Jonas Downey

It's hard to be good at your tech job right now

June 6, 2026

Codex's self portrait.

I’m writing this post because I want to say out loud what a lot of people are feeling: Working in tech during the AI transition is tough as hell.

There are pressures from all sides. Here are just a few of them:

Layoffs across the industry, especially reductions in management and support roles, as executives rush to replace human productivity with AI.
Mandates to learn and adopt new tools and processes incredibly quickly.
Shifting job requirements - like asking non-technical designers to become fluent with code-based workflows, or turning software engineering into an LLM-prompt-and-review lifecycle.
Obligations to accelerate work, do more with less, and increase your output.
A constantly changing market, where new breakthroughs and best-practice innovations launch nearly every week.
An influencer-led hype cycle pushing AI as The Way, along with a subtle or overt denigration of traditional ways of working.
A blurring of roles where non-experts can cosplay as experts because they created something with AI that looks credible on the surface.
A structural reset in how people build things, what they build, and the time and effort it takes to complete each step of the process.
Threats that entire job categories will be wiped out by AI advancements.

All of this adds up to a feeling of persistent intensity, and a sense of falling behind even when you’re working at max capacity. You have to rapidly adapt how you operate and how you spend your time.

Also: your job might no longer offer what attracted you to this line of work. If you loved to write code meticulously by hand – instead of asking a chatbot to write the code for you – you’re probably not super stoked about this movement.

And that’s not to mention the increasing public apprehension and negative impacts of AI on communities, which cast a looming shadow over the work whenever you have a rare moment to stop and think about it.

To top it off, the fragility of the job market leaves employees feeling more powerless to push back or share concerns openly.

Perhaps the most stressful side effect is the erosion of trust and confidence due to generative AI. It’s getting difficult to tell if something is real or fake, well-reasoned based on actual facts, or utter nonsense masquerading as truth. The worst case scenario is all of those at once. A truthy-looking document that’s half-accurate and half-bullshit is a dangerous document, because you need to look extra closely to spot the bullshit, and you might be accidentally lulled into believing it was all intentional.

Lately I’ve noticed my kids asking, “is this AI?” more often, and they’re increasingly skeptical of the information being presented to them. I find the same skepticism invading my work brain too. Did my coworker really think this through? Or did Claude Sonnet just half-ass a proposal based on some Granola notes?

We're facing an unstoppable onslaught of Brandolini's Law problems.

My kids are old enough to remember the world before AI existed, and maybe they’ll reflect on it like a before/after divide – similar to my memories of getting lost before we had always-on mapping devices in our pockets. It was scary, but we were unburdened by the shackles of constant ambient connectivity.

We were lost, but we were free to get lost.

The AI before-times will become similarly quaint. "Hey, remember when all information was authored by people?"

I know this post sounds pessimistic, which is odd coming from a person who works at an AI-oriented company. That’s exactly the problem: tech workers are experiencing these internal contradictions every day. Rejecting AI makes you obsolete, but embracing it comes with a laundry list of hard compromises.

I think the technology can be incredible when applied wisely, and I'm excited about the new creative potential it unlocks. Previously unsolveable problems are now solveable, and that kind of sea change is always worth exploring with curiosity.

Unfortunately, most of the tech industry doesn't take time for doing things wisely. It's structured to chase one gold rush after another, and companies are usually willing to go scorched Earth to win, without much consideration for what breaks along the way.

The AI movement is not particularly human-centered at the moment, and no one is presenting a counterculture argument for how it could be designed differently. Governments have little incentive or sufficient expertise to regulate anything. Frontier AI labs have all the control, but they're stuck between advancing the technology cautiously vs. building unfathomably valuable growth engines around it.

Let's remember that tech movements are not inevitable because some hype bros said so. Just look at the Metaverse or NFTs. It wasn't so long ago that web3 was going great. Tech only becomes inevitable when we recede into futility and allow the hypegrowth engines to roar unchecked.

Given the circumstances, the only way out is through. This has happened before: we pushed for web standards and accessibility, we pushed for health and safety in social platforms, we figured out the mobile revolution. Of course those things remain deeply flawed, but we made progress by speaking up and doing the work. This is a moment that requires the same. Our jobs are changing and so is everything else, but what hasn't changed is our responsibility to build with care and consideration for people first. It's hard, but that's the job.

This is my second post in a series on how design is changing with AI. Part 1 is here. Stay tuned for part 3.

Designing the wrong way is finally right

April 22, 2026

I've been designing software professionally for over 15 years, and for almost all of those years, I did it exactly the wrong way.

In 2013, I created prototypes in Rails to evaluate if we were making good decisions. In 2014, I made hand-coded websites since they were simple to ship and maintain. In 2016, I co-built a weather web app that eventually became a proper iOS app for the fun of it. In 2021, I finally learned how to design products in Figma. And then I worked at Figma for three and a half years, helping to launch a bunch of awesome creative tools for designers and developers.

For most of that time, I rarely embraced anything trendy in design at all. When Flash was big, I was doing HTML. When people were busy designing software in Photoshop, I was hacking the web. When Sketch and InVision were hot, I spent my days with chalkboard sketches and Sublime Text. Instead of designing mobile apps in Figma, I just worked directly in Xcode and Android Studio.

I'm not a contrarian on purpose, but I never saw the point of chasing after the design tools du jour because they're popular, or because someone on the Internet said they were the right way to do something.

I’ve always been focused on one simple goal: build useful stuff. When you can imagine something, design it, build it, evaluate it, and ship it yourself, you are unstoppable as a creative person. But that point of view made me a weirdo designer with an uncommon philosophy and skillset.

Working at Figma was the closest I ever got to the mainstream design zeitgeist, and from that experience, I learned the deepest depths about corporate software development. It helped me appreciate the coordination challenges and process overhead of large enterprises, and I gained a real understanding of why the industry firmly divided design and development into separate camps.

To be honest, I always felt a little uncomfortable about "drawing pictures of software" as a job, and the devout adoption of tools like Figma or Sketch as the only way to design. For rapid exploration and divergent thinking, those products are amazing and still essential. But when you’re ready to execute, why spend so much time fussing around with a representation of a thing, when you could just work on building the actual thing?

Fast forward to 2026, and the recent advances in AI tooling have made it dramatically easier for non-technical designers (or anyone) to build real working products. Suddenly the zeitgeist has crash-landed straight into my DIY approach. “Should designers code?” is so back! The wrong way is finally right.

The problem is: nobody has any idea how this new process is supposed to work. Now designers are hanging out in Terminals and engineers are vibe coding designs. It’s upsetting the whole careful balance that the entire industry had spent a decade or more establishing.

Our prior workflow…

designers draw pictures of screens.
designers give the pictures to developers.
developers build the screens.
everyone argues for a hot minute.
~ 1,500 Slack threads later ~
eventually we ship something that works.

…has now been compressed into:

everybody makes AI slop prototypes, which are 75% good but 25% annoyingly shitty.
nobody is quite sure what to do with them, but we’d better just ship something quickly to keep up with trends, and justify using all these Claude Max tokens.
also we can’t collaborate on making the slop prototypes better, because they’re a bunch of random bad HTML files and GitHub branches that we can't merge.
but anyway: who cares! ship! Do more with less! AI is the answer! (It’s the answer, right?)

as Karri wisely pointed out, this whole craze is speedrunning the prototyping and building part of the process, but often skipping over the “what to build??” part.

And the latter thing is what matters. Remember that the goal is build useful stuff, not just build stuff. The usefulness is the whole point.

Building some random software is pretty easy, and the cost of that is rapidly trending lower. Building great software that solves a real problem—and that real people enjoy using—remains an elusive sneaky bastard. I don’t see AI solving that, because it’s a human problem more than a technical one. But it can certainly help us find the answers faster.

I believe that eventually, the net result of all of this will be positive. Designers working directly with the real materials of software? Great. Broadening who’s able to demonstrate ideas with working code? Great. Accelerating the build process so we can prove or disprove ideas with less effort? Great.

We’ll just have to figure out how to make it all work in a way that’s sane and considered. My current advice is: slow down and make sure you’re investing time on impactful things. Typing a prompt into a slot machine and hoping for the best doesn't mean you’ve solved a meaningful problem. That's what Design (with a capital D) is all about!

This is my first post in a series on how design is changing with AI. Go here for part 2.

How to build a resilient design team

September 5, 2025

On the Figma blog: seven tips for building a team that's resilient to change.

Reigniting the spark of humanist software design

July 19, 2025

A while ago I watched this fireside chat with Jony Ive and Patrick Collision at Stripe Sessions.

Jony reflected on his experience as a college student, interacting with the original Macintosh for the first time. His feelings upon using the machine were exactly the same as mine: I need to pursue this same level of playfulness and care in my own work.

Of course, Jony went on to run design at Apple itself! But our similar early experiences reminded me of the reasons that I ended up in design in the first place. My interest had nothing to do with money, notoriety, or a specific technology. (If you cared about those things, becoming an artist or designer was a pretty stupid move.)

I was irrationally driven to create things that brought curiosity, joy, and utility to the world, like that early Mac. If I could help anyone feel how I felt when I first used that computer as a wide eyed 6-year old, then I would consider myself a phenomenal success as a creative person.

Many years later, I learned it’s not so hard to make a run of the mill product, but it's exceedingly difficult to make a great one. The secret art of great design is to put all of your enthusiasm, taste, and spirit into an object, such that it sparks an unspoken bond between yourself and the user. When they use the thing, they can feel your thoughtful consideration and care, because it vibrates out of every little detail. It's unmistakably obvious that you thought deeply about their experience using it.

In this way, you're not just making a product—you're making an emotional connection with people through that product. This is the ultimate pinnacle of the job, and it's tough as hell to get there.

It took me a long time to understand this. I’m not sure if I’ve ever truly achieved it, but that’s the root motivation that kept me going through a 25-year career working on creative tech. I still haven't grown tired of chasing it.

Over the last decade or so, it’s been getting more challenging to make things with that deep level of intention. It seems like the entire tech industry has been gradually eroding its soul (to the extent that it ever had one.) The incentives for building products today are inextricably tangled in matters of massive wealth, power, and growth—and all of those matters have been winning out for years.

Some of this is due to the taint of extreme capitalist influence in a market. When gobs of money pour into an industry, everyone's purity of motivation tends to fly out the window pretty quickly. Now you can either go tinker on a thoughtful thing in your garage, or you can earn generational wealth by doing some creepy AI stuff. It's not a big surprise that so many people choose the latter.

So that's one issue, but another problem is the way people build software and tech products today.

Creativity is like a fire. It's fragile and fickle, and it needs to be tended. It only burns brightly when the ingredients and conditions are just right.

To achieve soulful humanist design, you have to nurture that fire. You need quiet focus time to sit with a problem for a while. You need tons of practice and study to hone your craft. You need freedom and vulnerability to wander around and try 50 bad ideas, until the 51st good one materializes in an unexpected burst of inspiration. You need a strong eye for refining and distilling an idea down to its plainest essence.

You also have to care deeply about who you’re serving. Doing the right things for people has to be your guiding light above all else, and then you can build a respectful business around that.

And finally, you need the flexibility to be able to invent bold stuff. To try ideas that are totally unlike what’s come before. Your unique point of view and your values have to be baked into everything you create.

That’s how creativity works. But most modern software companies run in almost direct opposition to these points.

Need some focus time to explore? Good luck. There’s a constant stream of emails, chat messages, notifications, and meetings chipping your attention into tiny little slivers between obligations. Maybe you can get some creative time after work.

Want to care about customers? Cool, but how does that connect to our key business outcomes? How much recurring revenue will that deliver? What metrics can we swing upwards to beat our estimates? Maybe we can A/B test how much we need to care about people.

You wanted to be bold and inventive? Well, it needs to fit into our existing design patterns, so please be less inventive. And the bold stuff is hard to build, so please be less bold. Also, we didn’t have boldness and invention in the PRD for this project, so it’s out of scope right now. Since we have a launch deadline coming up soon, can we just try an MVP of this? Actually, let’s schedule a sync meeting to align on our objectives again. We can squeeze it in over your focus time.

The means of making software have turned into something of a production factory environment. We’ve piled a mess of constraints, guardrails, rules, tactics, and sprints on to the whole process. Creativity often happens around the edges, rather than being the core engine and purpose of the company.

This factory approach has an upside: it enables massive companies to operate at massive scales, so now the quantity and complexity of software getting built is basically infinite.

But how much of that software is actually good, and how much of it is crap? Every day we have more software that does more, but so much of it feels overoptimized, overcomplicated, underbaked, underconsidered, enshittified. Like it all exists for the sake of a balance sheet instead of any actual person using it.

So what's the remedy for this? I think it's twofold:

Someone running the company has to care passionately about high quality design—and they have to constantly prioritize that as a core aspect of how the company works. As a company scales, the quality of the work tends to go out the window, because care for great products gets overrun by organizational bureaucracy. That means the people in charge have to actively defend against this tendency, and regularly stamp it out whenever it creeps its way into the creative process.
Creators should be empowered and encouraged to deliver thoughtful, well-crafted work. A high bar for excellence has to be the default expectation for everyone. Empowering people means giving them more free space, reducing friction in making decisions, and blending boundaries between roles—ensuring everyone has the freedom to explore and build things they're excited about.

Weirdly, maybe AI can help?

Earlier in this post I made some snarky references to AI slop. I'm uncomfortable with the ethically dubious practices that have powered the AI boom, and I feel conflicted in embracing it.

Those (major) concerns aside, I'm cautiously optimistic that AI tech could improve our ability to create more things with deep consideration and care.

I realize this sounds strange. How could more automation result in more humanist design?

The answer is that technical contraints have always been the biggest barrier preventing people from realizing their best ideas, and AI is starting to help overcome those constraints.

I became more convinced during development of the new Hello Weather. There's not a single drop of AI in the product itself, but over the last year, we increasingly used AI code assistance to help solve problems that would have taken weeks or months to achieve on our own. In some cases we wouldn't have solved them at all.

Instead, we could go further and build something of higher quality, because we had help accelerating that process. And we did this with a tiny team under challenging time pressures.

If you harness these new tools in the right way, you become superpowered, and previously impossible things become possible. Then you can spend more time sweating the details on what really matters, and produce better work in the end. Your job doesn't go away—it gets even more effective.

In time, this could also serve as a counterweight to the organizational morass of enterprise scale companies, and give smaller teams more leverage to compete with big established products.

The key is that AI is not going to be the arbiter of taste and precision. It's not going to decide what's right for your ideas. It's not going to care about human perception or joy or humor. It's not going to understand your unique point of view and philosophy. It's not going to know how people feel in their bones when they use what you created.

That's the stuff that really matters. And it's all still up to us.

We don't have to settle for enshittified overoptimized slop. We can push against that by creating the antidotes.

It's up to us to design the world that we want to exist.

Building community on Bluesky

November 27, 2024

For whatever reason that probably isn't totally healthy, I love short-form text social platforms. The mix of humor, sincerity, shitposting, and real time information is a hot mess on the best of days, but all of that frenetic unfiltered energy has an unmistakable allure. It's like being in a panopticon of bored amateur poets.

Over the years, these platforms have helped me build connections and friendships, and played a large part in my career choices. I got my first job in product design because I saw a tweet about an exciting role, and took a moonshot attempt to make it happen. When I quit that job under public duress, the design community helped me out, and sent me countless messages of support on Twitter. (That meant a lot.)

I went to work for Twitter because I loved the product despite all its warts, and felt compelled to contribute to it. I ended up leading design for the main timeline of the app, the literal front door of Twitter. It was pretty damn cool!

Things were going good, but then the doors fell off in dramatic fashion. I decided to quit Twitter once as an employee, and again as a user a few months later. Since then, I've been sort of wandering around amongst the Twitter alternatives, giving a fair shot to Mastodon, Threads, and Bluesky for the last 2 years.

Short text vibe check

Mastodon and its technical underpinnings were all structurally great, but the wrist-slapping social norms, clunky UX, and lack of algorithmic feeds made it feel too insular and limited for me.

Then I tried to settle into Threads, but from the start I was deeply skeptical of the platform's product design decisions, draconian moderation, and big tech ownership. It was an uncomfortable alliance to contribute to an app that I didn't trust.

And then there's Bluesky. I was on there very early—I'm user ~30,000 or so—but the first phase of Bluesky was too feral even for my tolerance. Hellthreads, Alf kink, and lewd selfies weren't quite what I was looking for, so I kinda dipped out.

But the concepts underlying Bluesky were always incredibly compelling. The Bluesky project got started while I was working at Twitter, and our teams were working on a lot of the same ideas—custom algorithmic feeds, starter packs (we called them Followpacks), user-centered moderation controls, and more. These features surely would have landed at Twitter too, if it hadn't gotten X-ed out.

Since the US election, people have been fleeing X for Bluesky, so I thought it was worth giving the platform a second shot. It’s matured so much since the early days, and now the foundations feel solid, full of potential, and fully detached from the Jack Dorsey/Twitter origins.

Hello #designsky

I had no big intention of trying to build a community on Bluesky, but thought it would be interesting to play around with the tools, and hopefully get some friends together in the process.

I started by building a custom feed around the hashtag #designsky to understand how this worked. (Here's my first test post for this.)

There are several advantages to a custom feed:

it can be sorted in a ranked order rather than chronological.
it can have a mix of different inputs—like, posts with a hashtag, posts with keywords, posts from users on a certain list, and so on.
it can be very broadly inclusive or constrained, so you have flexibility in curating what shows up, and what the vibe is like.
it's super lightweight. People don't need to jump through a bunch of hoops to contribute to it or read it.

The Designsky feed felt pretty amazing even in its first version, and it picked up a bit of traction with some other designers. So I decided to keep going, and pulled together a starter pack of designers linked to the custom feed. Since then I've been gradually tuning all of this and expanding what shows up.

The internals of this setup are complex, because on Bluesky, starter packs, lists, hashtags, and feeds are all different concepts. I made them work together like this:

The #designsky hashtag is the unifying element that allows anyone to get a post into the Designsky feed. You can also just browse the hashtag if you don't care about feeds.
The starter pack is linked to the custom feed for discoverability, so if someone sees the starter pack, they can also find the feed.
I also maintain a separate list of designers who are in the starter pack. I use that list to automatically include designy posts that contain keywords (like "design," "UX," and that sort of stuff.) That way, members don't have to constantly tag #designsky for their posts to show up in the feed.
I added a second starter pack when the first one hit the 150-person limit.
These are all self-reinforcing feedback loops that help the community build traction in different dimensions.

All of this is very manual and annoying to maintain, and I don't have a ton of time for this! So I'm a somewhat lousy moderator of things. But it's been incredibly fun and rewarding to see the design community rebuilding itself and rediscovering old and new friendships.

Will this work out in the long term?

A platform's design and its underlying philosophies drive how people interact and behave on that platform. So far Bluesky is doing all the right things, both technically and philsophically. I'm optimistic that we finally have a new place worth investing in—for the first time in a long while.

Realistically there will always be capitalist pressures and a million hard problems to deal with on any social platform, and I wouldn't be surprised if those issues eventually happen on Bluesky too. But we can enjoy it while it's still great.

If you're on the butterfly app, please say hello! 👋🦋

Own your weirdness

May 11, 2024

Recently a designer reached out and asked this:

I love the visual and interaction design choices I have seen with your work. It honestly has a feeling that I can't find in other tools/sites out there. As it relates to your visual design choices (like the principles on your site "build weird things"), what has helped you get into that creative space where you feel free to experiment visually?

This is a good question that I hadn't exactly analyzed before! Thought I would share my answer here.

On the visual design side, it’s a little hard to explain because there are so many different aspects of how any design project ends up coming together.

My general approach is a combination of the following…

Having a short attention span, which always leads to exploring different ideas than I’ve tried before.
Taking any opportunities to be inventive whenever possible, rather than just doing the “usual stuff” that seems obvious or commonplace.
Striving to make things that have the friendly joyfulness and playfulness of old Macintosh UI, which inspired me heavily as a kid.
Caring about the craft, metaphor, and meaning of interfaces, just as much as the function of them.
Bringing in inspiration from non-software sources, especially art, nature, industrial design, and music.
Satisfying my own curiosity, and seeking the brief-but-euphoric feeling of making something you really enjoy using.

All together, this is a sort of mindset shift—giving yourself permission to think broadly, go against conventions, and then seeing where that takes you.

Oh, and one other important thing: people are weird. You and I are weird. We all see the world a little differently.

This is what makes you creatively unique. The trick is to own your weirdness, discover what you love, absorb your influences, and turn all of that into your own special taste, sensibility, and style.

Then mine that for all it's worth. It'll never let you down.

How to make a great case study

March 14, 2024

silly illustration by an AI robot

Lately I’ve seen some advice on social media about design case studies. People often recommend using a formula that’s likely to satisfy most hiring managers, like this:

Pick a project you worked on, and state the problem you were solving.
Explain how you arrived at that problem.
Explain how you tried to solve it.
Explain why your eventual solution was the best.
Demonstrate that it worked, with metrics and qualitative results.

That's a great start, but there's more to it than that! Here's a deeper way to think about it.

What’s a case study for?

A case study is a storytelling exercise. The point is to articulate certain unique aspects of your work experience.

This is not actually a story about a project. It’s a story about you, using the project as evidence of how you work and how you think.

With that in mind, you can see why only walking through the routine aspects of a project would be insufficient. Nearly every design process follows the same basic order of operations:

Customers were dissatisfied about something.
There was a business motivation to try fixing it.
The team did some research and narrowed down what to focus on.
They explored possible solutions.
They reviewed and refined the ideas.
They picked one and built it.
They shipped it and measured it.
It had positive or negative results.

This is just replaying how most projects happen. All of this is necessary, but it's not quite enough for a great story.

To make your story more compelling, think about what you'd want someone else to take away from it. What was special about this project, and how did it enrich your personal experience and point of view?

Was it…

Proof of great craft and sweating the details? A strategic gamble that paid off? A tough situation, like working with a difficult peer or a tight deadline? A new challenge you hadn’t attempted before? An example of your range, such as leading a team? A struggle or failure that taught you something valuable? A chance to invent something totally new?

…or other things like that.

Once you've put together a few of these on different topics, you can use them strategically for your portfolio or job interviews. Tell stories that represent what you care about, and relate in some way to where you want to go next.

There's no need for this to be overly dry or formal, either—don't be afraid to use your own voice and sense of humor. Design is messy, and nothing ever goes perfectly smoothly, so tell that tale! A great story has a bit of drama, insight, and levity. Bring your personality into the case study and it'll be a million times better.

P.S. it's always good to shout out your team in a case study, since most design work isn't made alone. You can do this while clarifying what your role was on the project, which helps a hiring panel get a better read on your experience.

Year in review

December 31, 2023

I don’t normally write year in review posts, but I want to start 2024 off right, so I’m doing this to close a few chapters and start some new ones.

Highlights

A great year at Figma

Following my unexpected exits from Basecamp and Twitter in 2021 and 2022, I was adrift about work, and uncertain whether I still had the energy to care about tech anymore. My professional identity was so tied up with those companies that I had to rediscover who I want to be.

I’m in my 40s, I’ve been doing this for quite a while, can I still hack it? Is there such a thing as a great second act? Should I even bother trying to have one?

I joined Figma with the hope that it would rekindle my spirit, working on a beloved creative tool with a ridiculously smart group of people.

I’m happy to say that’s how it worked out. 2023 wasn’t an easy year for Figma by any means, with huge launches and conferences to coordinate, the challenges of internal growth, and the major ups and downs of the Adobe acquisition. But the team has so much heart and enthusiasm that it spills over into everything we’re doing, and it turns out that’s all I really need from a job at this point.

I had the good fortune to work on Variables, Dev Mode, and a bunch of other big and small things we shipped in 2023. It was tough to pull off, but so amazing seeing all of this hard work land successfully. I felt incredibly lucky to be a part of it.

Finding my way as a manager

I’ve been managing teams for almost 5 years, but most of those years were clouded in some type of existential turmoil—ranging from shipping a new product amidst big public controversies, surviving the uncertainty of the pandemic and forced remote work, facing difficult social and political reckonings, trying to remain calm during the strange hostile takeover of a social media company, and riding the rollercoaster of the tech industry’s excesses and instability.

Moving into management is never easy, but doing this in 2019-2022 was a trial by fire on Extreme mode.

In 2023, I was finally able to breathe a little, focus on who am I as a manager, and get better at a lot of practical and philosophical things. In many ways I still feel like a complete newbie, but I think that’s probably just the reality of the job. Every day is always a fresh challenge you haven’t seen before.

I’m also lucky to have a super supportive crew of peer managers at Figma, which is something I never had in previous roles. I can’t emphasize enough how important this is—management is lonely, and you need people in your corner.

Side project progress

In February, we launched Weather Machine, an API service built on a complete rewrite of our tech stack that powers Hello Weather. This didn’t take off as we had hoped (more on that in the lowlights), but shipping this was a big achievement.

We also made a ton of progress on a complete ground-up rewrite of Hello Weather for iOS, which has been SO MUCH WORK. omg.

At this rate we’ll either launch the new app in 2024, or die trying. But this has been a great adventure as well, forcing me to get proficient with SwiftUI. I’ve done most of the front-end work for the app, and it’s been fun to work on, except for about a dozen things that are maddeningly hard to achieve with SwiftUI in its current form.

Personal stuff

Travel I went to New York for a week, visited San Francisco multiple times, drove the California coast from SF to LA, and spent a few perfect days as a tourist in my home city of Chicago. I love all of these places, and it was such a treat to see them.

Music We managed to nab tickets to one of Taylor Swift’s concerts at Soldier Field, saw the last Dead & Company shows at Wrigley Field, and Bonnie Raitt at the Chicago Theatre.

Here's my playlist from 2023.

Books I enjoyed Build by Tony Fadell, Department of Speculation by Jenny Offill, and Design as Art by Bruno Munari.

TV This was the year of The Bear and Doctor Who.

Family We survived, and tried to thrive. It wasn’t an easy year, but we’re still standing, so that’s a highlight?

Lowlights

Work/life balance

I haven’t figured out how to do management full-time while still nurturing my intrinsic need to keep creating and designing things myself. The side projects are nice, but they take a ton of time and effort, and it’s basically like having two different jobs. The net result is not nearly enough free time, and feeling pressure to be constantly productive, which isn't healthy.

Side project survival

Similarly, we were disappointed that Weather Machine didn’t have more success out of the gate. Hello Weather is still a net-negative financial endeavor, in that it pays for itself but it doesn’t pay for us to work on it (we essentially donate our time, and take occasional small payments when we can.) Our hope was that an API product could round this out, but alas, not yet.

Meetings and gap time

I’m an "introvert in denial," and the problem with remote design management is that you usually spend most of your waking hours talking to people on Zoom. I enjoy this, but it’s also very taxing, and I haven’t nailed the balance yet. Need to block out more gaps in the schedule.

Losing my voice

With so much going on, I haven’t had nearly enough time for reflection, writing, longform reading, and the creative play/exploration that I miss doing. I also spent a lot of effort trying to rebuild my networks on Mastodon and Threads, since I divorced myself from using Twitter earlier this year.

Health

It was a tough one for our family, with multiple bouts of Covid, and one of our kids being hospitalized with pneumonia, among various other issues. Glad we made it through.

Personal goals for 2024

I always overcommit to things, so this is it. Posting here for accountability!

Shipping Hello Weather.
Much more writing and sharing. Getting back to blogging, newslettering, and podcasting. (Longer term stretch goal: writing a book!)
A little refresh for this website.
Less social media, more books.
Being more present.

Happy new year, friends. Hope you have a healthy and joyful 2024.

Why side projects are essential for creatives—and employers should embrace them

October 5, 2023

Last week, an internal memo from Shopify's CEO leaked, stating that the company is tightening its policy about employee side projects. Here's a blurb from the memo, written by Tobi Lütke:

Shopify is like a professional sports team that requires our unshared attention. When you're at Shopify, we are building the entrepreneurship company for millions of entrepreneurs around the world, and that is our main quest. We all need to…think and act like founders, and build Shopify as if it is our own.

Although I understand this point of view, I think it’s a big steaming pile of BS. Here's why.

Nearly eight years ago, a friend and I started fiddling with the early ideas that turned into Hello Weather. At the time, we were hungry to learn about building iOS apps, but our day jobs didn't have a way for us to do that. So we decided to try making something in our spare time.

The project wasn't intended to go anywhere, but we immediately had a lot of fun working on it. It felt new and energizing, since we had freedom to make weird decisions that would never fly in a corporate environment. We had to wear multiple hats, and learn about aspects of product development that we hadn't personally experienced before—like setting up a business, doing marketing and promotion, deciding on pricing models, and a million other things.

Eventually, the app was real enough that we wanted to put it in the App Store, but there was a big problem: our employer had a tough policy about side projects.

The policy was a bit vague, but it was spiritually similar to Shopify's new stance. The gist was, please don't do stuff on the side. The company mostly wanted you to devote your attention and creativity to them alone.

I was feeling terribly anxious that our app would be blocked by the policy, so I reached out, explained the situation honestly, and asked for permission. Thankfully, the company was cool about it, and they revised the policy to be much more supportive about this sort of thing. We were able to launch the app and continue working on it for years after.

I'm so glad that happened!

That project is my favorite thing I've worked on in my 20+ year career. This modest little app remains the purest expression of how I want to make software.

It's been a valuable creative outlet, and a useful contrast to the strenuous complexity of working on massive-scale products. It also gave me a much deeper appreciation for what it takes to run a company, and what it's like to make all the tough decisions. (It’s really hard!)

Ironically, all of this made me much better at my full time job. I wouldn't be nearly as versatile or empathetic at work without this experience. The feedback loop between the two has been ovewhelmingly positive.

Now onto the “founder's mindset” that Tobi alludes to in his memo.

To be frank, this is nonsense. If you aren’t the founder of a company, you don’t get any of the benefits of being a founder. Expecting employees to act like company owners is extractive manipulation.

This ideology tends to take much more from employees than it gives back. They’ll develop an unhealthy mentality that their total dedication—and likely overwork—is essential to the company’s success. But it’s not, and most employees will never see personal returns like a founder might, regardless of how much they believe in the mission and grind it out.

Tech companies aren't sports teams, either. No one is getting international notoriety and multi-million dollar endorsement deals because they're great at programming a website! Let's be real about this.

And on the subject of ownership: when an employee leaves a company, they don’t own any of the work they did there. The company owns all of it, and they might even restrict people from sharing or talking about it at all. This is the opposite of being a founder with an ownership stake. The mindset thing is just a delusion.

To be clear—tech employees absolutely can influence the success of the companies they work for, by taking charge and driving work forward. But their level of commitment should be commensurate with their compensation and authority at the company.

So what's the best way to help employees develop a founder's mindset?

Let them found things! Give creative people the freedom to be creative in whatever dimensions they want.

The key is setting clear boundaries, and trusting people to honor them. A fair arrangement is like this:

No conflicts of interest – don’t work on a thing that’s the same as your full time gig. If you work at Slack, don’t make a chat app. This should be obvious.
Prioritize your day job – you agreed to work full time for a company, so work full time. That means 40 hours. Give the company your best, and don’t spend your attention at work moonlighting on something else.

But after that, the rest of your time is yours. If you have the chance, try a project that enriches your point of view or diversifies your experience. Don’t just do a side hustle; find a side passion. You’ll be better for it, and your day job will be too.

Threads & the terrible greatness of everything at once

July 8, 2023

Well, it happened. Elon took over Twitter, blew it up repeatedly through a series of befuddling product changes and self-owns, and now we have at least 3 other Twitters vying for attention. The newest entrant, Threads, has come bursting out of the gate with massive user numbers and a strong dose of millennial energy. Despite this (or maybe because of it) Threads feels like the first actually viable Twitter replacement.

Or is it?

Adam Mosseri, head of product for Instagram and Threads, posted an explanation that Threads is not going after "politics or hard news" due to the "negativity" of that subject matter. He also alluded to Facebook's proven inability to handle such material in a responsible way.

In short: we don't even trust ourselves to get this right, so we're not going to try.

This makes total sense from a big tech, corporate product perspective—especially coming from a company that has a not-insignificant amount of regulatory scrutiny hanging over its head.

And yet, that decision will probably extinguish the special sauce that made Twitter so culturally impactful.

The most succinct way I've found to describe Twitter is the terrible greatness of everything at once. Somehow, Twitter was able to capture a cultural zeitgeist, and collect many essential niche communities into one giant pool simultaneously. It was like a massive family gathering, with old guys ranting about the government, friends cracking inside jokes, celebs promoting their latest drop, stupid ads blasting at full volume, and weird kids taking lewd selfies in the bathroom.

On Twitter, all of those random people bumped into each other every day, and all hell broke loose. This is what made it so amazing, or so horrible, depending on the moment. It wasn't exactly real life, but it was messy like real life. And it had a real impact.

This happened because Twitter had a unique combination of product decisions, and lacked rules to enforce any specific decorum.

Software design often gets treated like graphic design: just a bunch of rectangles on a screen, or a series of buttons and inputs.

This is the wrong definition.

Software design is much more like urban planning or architecture. When you make software, you're defining the spaces and pathways that affect people’s behavior. You create the guardrails, and then people mostly follow them. It can be a position of great power and authority.

In the aggregate, all of your decisions—large and small—add up to the vibe of a product, just like the feel of walking into a house or a building. Is it cozy and friendly? Corporate and sterile? Ugly and messy? Risky and raunchy? It depends on how it was designed.

When I'm looking at these Twitter clones, what I really want to know is: where are the creative rebels? Where are the poets and writers, the artists, the anarchists testing the limits of what's acceptable? Where is Black Twitter? Where are the queer communities or youth activists?

These are the people who question the status quo and drive change over time. It seems like Threads doesn't want them, because they're going to be content-moderated and probably downranked into oblivion, unless they follow all the proper normie norms that the platform designed on purpose.

Which they won’t.

As a result, they probably won't hang out on Threads either. A sanitized Zuckerberg property is not the place for the next generation of punk kids. Threads will be fine for exchanging silly pleasantries with your fellow 35 year-olds, posting vacation pics, and seeing stupid jokes from brand accounts. But the deeper, tougher conversations are likely going to happen somewhere else.

For a while, all of that happened in one place. It was terrible, and it was great.

The daily haiku

January 1, 2023

In 2022, my kid and I challenged each other to write a haiku every day. It was difficult to compose and share all these poems, so we also started making an app to help us write together. We'll release the app later this year (hopefully!)

Throughout the process we gained a new appreciation for poetry and the forced economy of three lines of text. It was fun to surprise each other with strange words or unexpected combinations.

The list below contains every haiku I wrote. When you write one every day, most of them are terrible, but there are a handful of gems scattered throughout. My faves are marked with an extra highlight.

January

the very first time
there is a long road ahead
and that is the joy

existentially
i have some questions
but no time to ask

the clock is ticking
we hear it in the present
which is now the past

the curious things
we haven’t imagined yet
could become real

who absconded the
pop-tart that had been toasted
breakfast was ghosted

there were retractions
of the redactions hiding
legal infractions

sorry we could not
pay attention. our accounts
have been overdrawn

representatives
are standing by, please press one
until they sit down

a light extinguished
abruptly stopped, left no trace
but we remember

this hullaballoo
cacophanous balderdash
all mumbo jumbo

icy epitaph
of previous days frozen
a graceful stasis

please dear never mind
the right words i could not find
dropped out of my mind

empty shelves out of
stock markets breaking all time
record low morale

all the commuters,
computers, distributors
remotely working

these unusual
times have become usual
to abuse you all

sadly risible
a problem divisible
and invisible

we did not care for
your thoughts but you still put them
on this damn web site

phone rang three more times
unknown caller voicemail
pyramid scheme grift

our company is
like a family except
we will control you

a saturday night
fever dream imagining
alternate futures

if somewhere there is
another plane of spirits
i hope i see you

i want to go home
but this place is no longer
the same as it was

cracks in the plaster
looking up at the ceiling
is that a new one

hey i just met you
and this is crazy so here’s
a retraining order

hallucination,
imagination, or in
a simulation?

the robots have tracked
you and tried to distract you
it worked they hacked you

ambiguity
in all the words that you said
left me feeling cold

reflective sunrise
blasting through the cracks in the
curtains awakened

peering into a
dewdrop mirror image of
infinite spaces

off in the distance
past all the trees, did you see?
capitalists

feeling uneasy
burnt coffee tv static
water left running

February

all these sycophants
devotees and followers
attention hungry

hyperbolic noise
undulating through brainwaves
like stinging nettles

loading loading please
wait loading loading please wait
loading loading please

rainbows and meltdowns
unicorns and malady
glittery sadness

timely just in time
time out losing track of time
timeless out of time

eyeballs and hive minds
wasted on cheap bravado
polemic bombast

ringing in the years
wringing hands in latent fears
ringing in your ears

these unexpected
surprises snuck up like thieves
of our intentions

transmissions and codes
linking distant souls like a
ouija board seance

lost my mind somewhere
in aisle nine next to the
pickles and regret

chasing success and
grinding vanity hustle
bloodshot consequence

current resident
you have been selected to
throw away junk mail

confederate flag
urban assault vehicle
parked at chick-fil-a

image degraded
specific memories now
unfathomable

you irascible
scallywag with your crackpot
theories and grousing

staring into the
middle distance you left me
these obfuscations

running uphill you
appeared like magic and we
both ran together

what things did you see
before all this existed
when you were brand new

sacrosanct rules
built on indefensible
careless positions

psychedelic hues
maximum velocity
eyes closed spinning dark

self esteem self care
self conscious self aware self
loathing self despair

tiny little man
desperately trying to be
a really big deal

way in the future
wave from your flying car and
remember these days

grasping at straws or
gasping for air, parked out on
this bridge to nowhere

feeling sheepish
we did not anticipate
your savage actions

mountains sliced in half
streets carving up the river
vehicle worship

imperceptibly
subtle changes happening
slowly but quickly

March

stumbling backwards
repeating history for
deluded glory

the frenetic flap
of a hummingbird’s wing
to achieve stillness

what luck and fortune
to have a charmed life was it
karma or privilege

blast radius shock
waves crashing in from the sea
shell artillery

incredulity
institutionalizing
animosity

we taught the machine
to teach itself so it could
manipulate us

words words words words words
inundation of way too
much information

is this really a
worthwhile use of your time
shouting on facebook

the living dead heads
of state of mind your business
acumen at work

password secret key
finger print face ID i
am not a robot

all hopped up on corn
syrup and jingoism
crowds chant USA

star dust assembled
spontaneously grateful
you are here with me

hung out to dry with
your laissez-faire attitude
and banal ennui

quarterly metrics
targets and strategic goals
while burning the earth

walking a tightrope
dodging lacerations from
this porcupine mood

swig another drink
in a blustering brain fog
going through motions

moonlight obstructed
radiating light shadows
hazy silhouette

making excuses
petty justifications
soothe fragile egos

hark! forsooth! crikey!
dagnabbit! bollocks! blimey!
gadzooks! tarnation!

i don’t recognize
the aged visage looking in
the rear view mirror

pea pods paw pads see
saws crawdads meemaws doodads
scrimshaws TV ads

business man on a
corporate retreat slinging
pie charts and cocaine

magic god truth or
lies 5G conspiracy
what do you believe

between consciousness
i left all my best ideas
inaccessible

a slight objection
to your deflection which was
gaslight projection

dropping connection
weak signal breaking up
we lost each other

i’m trying to get
this over with but i still
can’t get over it

claustrophobic fog
of unreasonable pressure
you put on yourself

stop speaking in codes
nonsense jargon and lingo
two plus two is five

April

restoration or
intrusion, chemtrails or clouds
nature or human

dull stinging heartburn
residual from caring
more than we should have

drugstore fluorescent
sterile bottle painkillers
$21

clouds part sun ray bolts
squint eyes look down touch soft ground
pulse race head throbs crash

hollow claims punching
down ginning up outrage with
alternative facts

the rattling air ducts
a pencil stroke on paper
distant road noise hums

emotions hung up
like pressed shirts in the closet
languishing unused

electric lamp beams
disrespectful light into
the sacred dark night

system entropy
chaotic armageddeon
let’s go to the mall

confrontations and
escalations drumming up
these palpitations

fading sun light on
the horizon remember
all those times we had

spinning lately in
circumspect spirals lacking
confidence or spunk

jumping the tracks and
leaving pennies to get smashed
thrill of breaking rules

unacknowledged
despair left silent, buried
is eating at me

constant wavering
assertive indecisions
permanent changes

biding time until
the collapse or renaissance
villain or hero

spotted a UFO
watched a sea creature rise up
no one believed me

smoky orange scent
acidic metal taste of
adrenaline fear

freefalling into
unexpected dimensions
the ripcord has failed

casting lines off the
roof of the parking garage
late summer sundays

trying to silence
the noise within and look calm
so no one can tell

buzzing frequency
vibrating off of your head
nagging subconscious

stop invading my
headspace like a stray dog who
jumped over the fence

press this series of
buttons and you will control
all of the puppets

hey let’s make a deal
door number one two or three
sorry they’re all traps

worn creases on your
denim jacket, lines on your
forehead, past present

accept all cookies
terms of service I agree
skip ad like subscribe

take a break in half
just keep your head down the drain
carry on fire

your circuitous
twisted logic lighting gas
and blowing whistles

hot steam rising off
the pavement billowing haze
wilted humid minds

May

16 hours grinding
left catatonic and numb
8 hours silent

alarms and sirens
honking horns and blinking lights
but nothing changes

lavender hand soap
cotton candy sedative
kiwi root canal

i’m keeping busy
appearances of progress
calendars booked up

coffee left on a
little too long but drinking
the burn anyway

the gilded age of
anxiety influencers
desperate hustling

exit door blast off
hurtling through great heights until
concrete reunions

the sweet relief of
hot sun pouring through a cracked
sullen hazy gray

memories faded
in blurry outlines of past
love and adventures

we did not bother
to follow the rules due to
distrust and boredom

the temporary
silence projects visions of
future loneliness

oh hello we have
some news for you. everything
is pure chaos. haha

ring ring ring ring ring
ring ring ring ring ring ring ring
smash the snooze button

i will not abide
this divide over which you
preside amplified

gumdrop rainbow bright
tie dye circumstance skate shop
lilac escapade

there is a lot of
hot air blowing out your mouth
are you a balloon

chipped away at all
the energy we once had
now a burned out husk

hot cinnamon bun
sugarcoated dragonfly
afternoon mai tai

forgot why I wound
this string around my finger
so not to forget

phone rings computer
dings oven sings dryer bings
always nagged by things

carbonated air
conditioned pressure treated
shrink wrapped bleached and starched

all aboard this ship
never mind those loud sirens
please ignore the leaks

trading hours spent
at this glowing rectangle
to pay for free time

edits of updates
of revisions of changes
to all the edits

setting reminders
to schedule future events
to feel productive

please pass the mustard
this stale hot dog tastes like
diesel gas and wax

fog fog fog fog fog
lacking energy to think
or think of thinking

tunneling to the
other side of the world
to escape despair

interrupting worms
digging into habitats
for vegetables

blistering rays of
moonlight dancing on the roof
of your toyota

stop asking questions
about this self anointed
empire in ruins

June

brushing the dirt off
the sprouting of a seedling
hello bright white sky

breaking news reports
the same horrible thing that
just keeps happening

thou shalt not break thy
rules or thou shalt regret thy
deserved comeuppance

serenade infused
melodious energy
into my brainwaves

melted hot concrete
fried eggs and exhaust fumes
sun imposition

leftover sandwich
used to taste better but now
a soggy remorse

how are you doing
how was your weekend how are
your intrusive thoughts

dear sir or madam
we regret to inform you
nonstop for profit

bionic tonic
supersonic mnemonic
stereophonic

effervescent fizz
refreshing when you cracked the
bottle on my head

pouring chemicals
for grass that shouldn’t be there
killing weeds that should

bonded magnetic
effect surprisingly still
unbroken through years

crossed lines frequencies
ricochet word salad mush
across the wires

acquisitions and
contracts very cool very
legal very cursed

corporate julie
from downstate stuck alone in
fluorescent spreadsheets

purchased butts estates
a lovely gentrified place
full of total butts

little bird perched on
a blue plastic tube waiting
for the end of this

the applicants and
supplicants beseeching the
grants and sycophants

honest bulletin
announcing the lies framed as
truths by the liars

we won’t tolerate
that which offends our strong
righteous tolerance

AFAIK
IOU ASAP
JK IDC

trading cash for memes
fake coins and frauds made up to
make money and run

disclaimer fine print
everything we said was false
hope you were convinced

why did you eat that
gastrointestinal rage
stop belly aching

why this unforeseen
lethargy taking over
is it apathy

chartreuse turquoise smile
charcuterie tortoise smell
charcoal target small

horizontal line
stillness without inertia
pain interrupted

choke down these six pills
for the next five days so that
you will keep breathing

July

broken fever dream
collapsed in a frozen pool
unable to swim

rendering any
original thought will take
too much energy

wheeze and sleep this day
away while contemplating
mortality thoughts

what price will you pay
for the indefensible
freedom you worship

oh hello this is
another report from here
it’s all just the same

lingering inside
these four walls I can access
the world but not you

negative nay no
zip zero zilch nothing none
nada nary nope

this sunlight above
feels radiant and warm like
old friends forgotten

substitute candy
a valiant attempt but tastes
like disappointment

misconduct and greed
in twisted sordid scenes like
hieronymus bosch

intractable fool
obstinate ignoramus
indelible dolt

eternal robot
reincarnated again
as a new robot

what is this strange noise
emanating from this phone
why are you calling

rubber neck steel toe
glass house wood chuck gold star stone
wall chain mail string cheese

what random access
memory retrieved this lost
old note from beyond

the last sliver of
daylight disappears behind
the horizon, blue

hey siri hey google
alexa! can you hear me
please stop listening

the smell of burnt toast
lingering in this kitchen
butter sitting out

your neutrality
is maddening please decide
you’re not switzerland

this machine is not
accepting cash deposits
unclear what paused it

that bulwark stalwart
walmart pop tart matriarch
porch plastered hallmark

circling in place
passing by points visited
pretending they’re new

monsters hiding in
your mind’s attic waiting for
rude interruptions

synthetic parties
and prosthetic emotions
posted to insta

heart accelerant
fast forwarding rapidly
hanging on for life

shopping mall yoga
vitamins and supplements
schemes to get rich quick

poltergeist haunting
the sock drawer inconvenient
horror laundromat

August

trading your life’s time
for numbers in a spreadsheet
amid restless nights

32 winters
since the old river ran dry
this desert wasteland

checking your schedule
looking for blocks of free time
you’re not free at all

cantankerous joe
rides a miniature bike
on the submarine

why is the tv
advertising volume cranked
up to eleven

hi hello good day
a new opportunity
to stay in this rut

smooth saxophone jazz
wafting from the loudspeaker
while the bombs rain down

deadlines killing me
need a lifeline to keep from
lyin dead on the floor

dramatic mambo
dancing aliens from space
popping by for cake

some dull engine roar
off in the distance bleating
toxic atmosphere

the fear of regret
left a bitter aftertaste
resentment stasis

all the vibes are off
nothing works when you need it
works fine when you don’t

impenetrable
fortress government building
intimidation

microscopic drops
of pop atop mop top cops
coke crimes chop shop flops

skipping stones off the
pier watching waves roll in from
speedboats far away

popcorn popping on
raindrops dropping on (the roof)
bops bop bopping on

holding on for me
nothing left to give to you
selfish introspect

backache radiate
dull twinge of electric shock
in nervous networks

this indecision
calling attention to your
lack of bravery

waves in lockstep with
the orbiting moon sending
sultry vibrations

pachinko machine
chirping sweet persuasions and
taking your money

unexpected frog
appearance showing up by
surprise in this room

texting five feet from
each other separated
by air and drywall

September

hi mister cool guy
ray ban sunglasses sun tan
linen pants yacht rock

conspiracy schemes
posted on 4chan riled up
the nerds and memes

glued to devices
forgot how to think clearly
can’t pull to refresh

melancholy breeze
passes by summer’s last gasp
portending the end

legal proceedings
shouting negotiations
peanut gallery

seismic pressure broke
cracks in the pavement patched by
dinosaur petrol

wrong left turn left me
alone left out to dry left
behind in left field

conflicted worries
mixed into confusion soup
noodles of panic

torrential waves pour
over coffee subconscious
background mind freakout

wicked bingo game
disclaimer five in a row
summons the spirits

administrative
bureaucratic cubicle
autocratic rule

wearing a mask to
hide the truth or protect the
others from knowing

that nonconformist
t-shirt you like is half off at
urban outfitters

4am jolted
awake by uncertainty
spinning in the dark

permanent mellow
unending apathetic
consistently meh

revelatory
optimism of what has
yet to be explored

never mind the brain
sending rational commands
working against you

busy bulls buzzing
big bad business bureaucrats
belching beta bets

October

we changed when our
trust fell apart and couldn’t
be reassembled

we have considered
all the facts and concluded
you are an asshole

please insert card now
do not remove card do not
REMOVE CARD RIGHT NOW

hyperbolic hell
hysterical heightening
hyperventilating

we had objections
your dishonest deflections
feigned disconnections

is escapism
healthy self preservation
or just negligence

felled a redwood tree
to craft the furniture that
went right out of style

lemon rose spirits
sprinkled onto bacon wrapped
gentrification

when you changed the world
did you make it better or
just cash the paychecks

please excuse me for
being out of touch due to
insecurity

some crumbs i found in
the couch from a previous
past version of you

let’s go back to where
we started and do it all
over but better

disconnecting from
everything left me alone
in new potential

interruptions keep
breaking my concentration
attention pre gone

here is a story
that makes me sound smart without
saying it outright

pineapple pimple
peanuckle pinnacle people
pickle popsicle

November

we narrowly dodged
a terrible accident
and laughed in panic

do you think about
when we were kids and loved each
other so madly

this humble maudlin
blue atmosphere is fueling
morose disquiet

has naiveté
made you foolish or is it
a pathway to joy

your impossible
choice led me astray into
unwanted darkness

life is loaded with
regrets if you second guess
i guess i shouldn't have

oh hi reply guy
why you gotta drive by my
side with your stink eye

reading letters i
wrote twenty years ago that
sound like someone else

crawled into bed late
blurry eyes spy shadows and
foggy memories

trademark copyright
all rights reserved but they stole
your work anyway

painful words barb from
your mouth like shards of glass sent
right into my heart

have you completed
all of your tasks for the day
productive human

fiber optic lines
transfer at the speed of light
all of these cat gifs

this plastic bottle
will outlast us but pretend
to recycle it

rose colored glasses
lied to me! everything was
in fact terrible

turn the oven up
to 450 and throw in
all the pizza rolls

December

keeping your trinkets
coffee cups and collections
around for comfort

i'd like to connect
to your unprofessional
network of shitposts

double up double
down double header double
trouble double dare

what recalictrant
ossified calcified stale
retrograde thinking

copper pipe lukewarm
tap water concrete footprints
vinyl furniture

microwave popcorn
live tweeting rubbernecking
the apocalypse

text messages like
postcards we forgot how to
talk to each other

manufactured text
generated by machines
presented as human

platinum gold rewards
premier executive club
ultra super wash

permanent absence
makes this cold month colder still
i miss your laughter

despite everything
and all the complications
we are still hopeful

syncopated beat
secret rhythm entrancing
uncontrolled brain candy

sorry to disturb
you but ignoring problems
does not help solve them

manufactured cheese
product may contain traces
of wheat, soy, milk, soul

there are too many
cats wandering around here
it's freaking me out

computation and
algorithm automate
emotional state

maybe next year will
finally be the one that
feels relaxed again

60 24
7 30 52
365 time

exhuming old feuds
to reset for a new year
bygones gone to hell

The soul of a company

November 20, 2022

There have been approximately infinity thinkpieces about Twitter lately, so I'm hesitant to write another. But there is one aspect of this whole circus that I felt was worth calling out.

Some people have been comparing Elon Musk's corporate takeover and internal upheaval with Steve Jobs' legendary return to Apple in the late 90s. Maybe if you squint hard enough and suspend all reasonable doubt you can make this connection, but I think Elon is operating like the exact opposite of Steve.

In Apple's case, Jobs and crew had created a little renegade computer company in the late 70s, focused around a newly humanist approach to technology. They developed a strong vision of what personal computing could be, and that vision was already highly concentrated in their early products. Look at this 1984 release video of the original Mac. That product, and that company, already had a personality and a soul that was unlike anything else out there.

But as a business it was shaky, and Jobs was an unsteady punk who lacked discipline. So he got kicked out of his own company, and spent years away from Apple developing a stronger point of view about making computers and running businesses.

In the meantime, a revolving door of corporate goons took over Apple and tried a bunch of Haha Business product strategies that steered the company away from its humanist roots. It became a sad husk of its former self. At the low point, Apple's product line was confusing, stale, overpriced, and getting dunked on by clone manufacturers who were making more powerful Macs for less money. (I owned one of the clones during this dark era!)

When Jobs came back to Apple, the company was in free fall. He brought over inventive tech from NeXT, along with a decade of extra wisdom. He fired the corporate goons, drastically simplified the product line, and launched a bunch of new products oozing with that same concentrated vision we saw in 1984.

He restored Apple's soul. His best articulation of this was the iconic "intersection of liberal arts and technology" presentation in 2011.

OK, now on to Elon. Is he saving Twitter like Jobs, or destroying it like a bull in a china shop?

The answer depends on how you define the soul of Twitter. This is somewhat up for debate, because nobody has ever quite figured out what the hell Twitter is supposed to be. The company's most recent vision statement was "serving the public conversation" — a line vague enough to be interpreted in 100 different ways.

But if you parse it out, there's something meaningful in that statement. Twitter is about democratizing global access to information in real-time, and importantly, doing so in a way that's as safe and healthy as possible for everyone who participates. There is a strong humanist sensibility in Twitter, just like Apple.

Due to the nature of the product, Twitter has to operate more like a government than a company. It needs to look out for everyone on the platform, listen to them, and continually balance strategic decisions with the ever-shifting grounds of global culture. Twitter is about giving people a voice, taking care of them, and speaking truth to power. It will always be imperfect in the same way that democracy is imperfect. It needs its employees to care deeply about perfecting it anyway.

And that's why I think Musk is the opposite of Jobs. Mechanically you could argue his approach is similar (coming in hot, shaking up the company, firing people, and so on.) But his actions so far completely contradict Twitter's roots. Free speech absolutism does not make a platform safer. Brutalist leadership does not create a healthy environment for sharing ideas and making difficult ethical choices. Moving fast and breaking things will erode trust. Eliminating the inclusive culture makes it harder to represent the broad global population that Twitter supports.

It's possible that Elon will turn Twitter into some different thing that becomes successful anyway, due to his memelord reality distortion field and interminable hero worship from like-minded techbros. But he is not a Jobs-esque visionary who's righting the ship after it got off track due to mismanagement.

He's much more like the clumsy corporate goons who wrecked Apple after Jobs left. His ownership is rapidly chipping away at Twitter's soul. It may never come back again.

Processing painful work exits

November 5, 2022

Right now I'm feeling raw about the big changes at Twitter, and the implications for so many wonderful, dedicated people I worked with. They've been forced to figure out new life plans due to many factors out of their control.

I've been down this road before, and struggled mightily to get through it, so I'm sharing what I experienced in case it helps anyone feel a little less alone processing the turmoil.

The identity problem

One major cause of suffering was that I had associated my identity and personal sense of self-worth with my company and its culture. Although I was not an owner of the company, I felt invested in its success over many years. I was a vocal champion of our work, and I was proud of it.

I had failed to reconcile that critical detail: I was not an owner of the company! It all belonged to someone else. And they could do whatever the hell they wanted with it at any time.

Eventually, I realized I could still be proud of the work, and stand by my principles, without working there anymore. Of course your self-worth has nothing to do with your job, and I was foolish to associate them so closely. But it took a while to unbundle all of this emotionally. You can't rationalize your way out, or accelerate feeling better, you just have to take the time to process it.

The traumatic event

Even if you see this coming, it still hits you like a sack of bricks. On the surface it might sound silly to grieve a job loss, but if you've poured a significant chunk of your life into it, and built key relationships and friendships, it's absolutely a massive change. This is even more profound when the job was a great fit for your personal values, because you naturally developed a strong attachment to it.

It's exponentially harder when your exit from the company happens without sufficient care or courtesy. A severe, unexpected event can be deeply traumatic, because it feels like a total betrayal of what you believed and built.

The imposter syndrome

Another major challenge I suffered was questioning whether I was even good at my job anymore. After you've spent a few years at a company, you'll develop an internal reputation and institutional knowledge that's not transferrable anywhere else. When you cut ties, you have to give all of that up and start over.

This gets harder the longer you stay at a job. Going from a 5+ year role to a brand new one can be really disorienting. Some of your skills may have atrophied due to working in a particular way with a particular team. Or maybe the industry has changed and you haven't. You feel like a newbie, except now you're an oldie.

This is something you just have to face head-on, and the fresh start might end up being incredibly fruitful. In my case, I learned to work in different ways, made new relationships, and gained wisdom through the process.

Give yourself plenty of grace and time to figure this out. Remember: you're clearly very competent, or you wouldn't have lasted at the job you had. You'll be competent at the next one too!

The financial impact

Depending on your situation, this can be so terrifying. I don't have a super healthy relationship with money, and I had no experience floating without a paycheck for an extended period. I was also the only person supporting my family. All of that caused a lot of worry, even though we were totally fine for a while.

Ultimately I figured out that you can (and should) take breaks between jobs, and there are lots of strategies for handling that. Those breaks can be some of the best times in life, because you're unburdened from the daily grind. If possible, try to set aside the worry and be a free human for a month or two.

The subconscious stuff

With all of the above compounding at once, I was having all sorts of trouble. I was sleeping terribly, frequently waking up in a panic, acting cranky, trying to get a portfolio together, overscheduling my calendar with interviews, trying to keep up with former coworkers, etc. There was a low grade subconscious stress that persisted for a long time.

You can't control your subconscious, but you can help it chill out a little. Get plenty of fresh air and exercise, do meditation or therapy, drink a glass of wine, and pace yourself.

The next steps

You might not know it yet, but you're already stronger. Literally right now, today, you are stronger, even if you can't feel it. This will be an opportunity to reevaluate your priorities, with a more sophisticated lens than you had last time.

My only piece of advice is this: don't lose your idealism or become cynical. Remember the joyful moments, the successes, the friendships, the meaningful things you learned, and bring those with you. Try to set aside resentment or toxicity. It's not worth wasting brain cells ruminating on stale water under the bridge. (I will admit, this is much easier said than done.)

In order to do that, you might have to sharply disconnect from that past job. Mute or block news about it, delete social media stuff, or whatever you gotta do to put it in the rear view mirror.

In times like these, remember to say, "Thank you, next!" And lean on your support network too, because they will get you through this.

To manage or not to manage?

October 19, 2022

This year I've been coaching some designer friends and hearing about their struggles and career growth. Aside from "should I code?" the second-most common question is "should I move into management?"

There isn't an easy answer, but here are some tips to help you figure it out.

Are you able to stay balanced in trying times?

When you're a manager, dealing with tumultuous times is a core part of the job. This is because people are messy, and the world is messier still. Your team will have unexpected struggles, crises will occur, projects will get killed, orgs will reorg, coworkers will quit or have performance problems. There will always be interruptions and fires to fight, not to mention that times are tough outside of work too! You have to handle these challenges without getting bowled over.

Will you find joy in others' successes instead of your own?

Pro tip: you shouldn't be getting credit for your team's great work. Your team should be getting that. Your job is to create an environment and framework where people can thrive, grow, and bring ideas that far exceed your own.

That means you'll be evaluated based on whether other people are succeeding. This is critically different from being an IC designer, where you can directly manifest your own destiny by producing impactful work that's delivered on time.

Can you handle rapid context switching, overcommunication, and coordination?

A huge part of your job will involve talking all day about different topics in quick succession, making sure multiple simultaneous projects are on track, sharing information, sharing that same information again with another group of people, and so on. No matter how good you are at this, you probably still won't be that good at this.

It necessitates a consistent energy level, positivity, and a lot of empathy, because everyone on your team will have differing levels of understanding and needs for support.

Do you prefer working on granular problems, or broad collections of problems?

One fun thing about being a designer is the opportunity to get really deep on a specific project and focus on that. Maybe you're working on a new product feature, and you have 4 weeks to explore a range of different solutions and edge cases. You can dive into all the finer points.

As a manager, you're generally zoomed out a couple levels past that. You're looking at resourcing and execution across a range of important projects, both current and in the near future, and figuring out how to sequence them into a logical and meaningful progression. You won't know exactly how these problems will be solved, but you know that it's roughly possible within the constraints you've determined.

You do still have to dive into the finer details periodically, but it becomes a much smaller fraction of your day-to-day.

Are you OK with being unpopular, and making tough calls?

If you're a leader, you'll have to make unpopular decisions sometimes, and you're going to get criticized. Some of that criticism will be shared directly so you can make changes and improve, but even more will be happening privately. (The stuff you don't hear about is always more concerning.)

People will routinely question your vision, your fairness, and your weaknesses. That's because you have real authority to make decisions that affect people's professional and personal lives. With power comes responsibility.

You can earn your team's trust over time, you can be empathetic, and you can build a reputation for making good calls. But no matter how great you are at it, the power dynamics will still fundamentally separate you from the team that works for you. You have to build up a new support network of peer managers elsewhere.

Are you on board with the company's processes?

One last thing. If you're a manager, you become a company steward in a way that you weren't before. As an IC, you can be pretty rogue about your approach to work and how you act. If you're getting your work done, there's a lot of wiggle room there.

But as a manager, you end up safeguarding a lot of sensitive information about planning, performance, and interpersonal relationships. You have to stay more buttoned up. And you have to follow the processes the company has in place for those matters.

This means you need to be bought in to how the company thinks about management and process generally. If you strongly disagree with the way the company operates, you're not going to want to inflict those policies on your team, and it's going to be a constant struggle for you.

Make sure your own principles are mostly aligned with the company before you put on the manager hat.

Expansive and reductive modes of creative thinking

February 12, 2022

When you’re working on a creative problem, there are two major mental modes you might find yourself working in without consciously realizing it.

Expansive mode. This is usually what happens at the start of a project when you’re not exactly sure which direction to go. You expand your options by exploring a lot of possibilities, then see where those paths take you next.

Reductive mode. This happens when you’ve made decisions about the general direction, and you need to hone an idea and build it out. You reduce unknowns and gain confidence by working through finer details.

Occasionally a project is straightforward, and these modes happen naturally in a linear progression from expansion to reduction. But usually, projects are messy, and you end up vacillating back and forth.

When this happens, it’s critical to be aware of when you’re changing modes, and to make sure you have a good reason—because this is what can derail a project.

As an example, let’s say you’re working on a new app. After considering several different information architectures, you’ve decided to organize the screens into tabs. You start building out each tab, until you run into a problem: there are more screens than you expected, and they won’t all fit into the tab space.

At this point you might start questioning whether tabs were the right choice after all. Maybe a menu would be better? That sounds interesting, so you spend a day on new mockups exploring menu designs.

Well, a menu might be fine too, but now you’ve just blown extra time relitigating a core decision that you already made earlier, which likely has other cascading effects. This is the sort of change that can blow up a 2 week project into a 2 month project.

The reason? You jumped from reductive mode back to expansive mode. This should only happen if new information has totally invalidated your prior decisions and forced you to start over.

In this case, were the tabs really out the window? Maybe it’s OK to have a limited number of tabs. That means we’d need to prioritize the most important screens, and then figure out secondary navigation for everything else.

Regardless of which direction you ultimately choose, the key is being disciplined and conscientious about mode switching. If you feel strongly that you made a bad call, of course revisit it and go back into expansion mode. There’s no need to double down on a bad design. But you must be willing to accept the extra time investment it’ll cost you to get sidetracked.

Mind your mind modes and you’ll be more intentional about the choices you make, which also improves your efficiency in the long term.

Software’s missing humanities

February 7, 2022

Recently I asked my design pals on Twitter about their background in psychology, sociology, or human-computer interaction. Of course you can’t draw scientific conclusions from social media polls, but the results roughly matched what I would have guessed based on my own experience. Only about 20% of designers had formal training in these areas, with most identifying as self-taught.

Maybe it’s just me, but I think this is a problem! When you distill a product designer’s job into focus areas, there are 4 broad things they need to know really well.

1) The craft of product design. This one is obvious, and it’s surely what most designers focus on most. You need to know color theory, typography, visual hierarchy and layout, information architecture, interaction patterns, and how to combine all of that into a clear, usable interface. You also need to learn the tools that help you produce this work, whether that’s Swift, Sketch, CSS, or Figma.

2) The process of product design. Knowing the craft is fundamental, but it’s still not enough to get anything done. For that, you need to understand the varying phases of product work, from explorations to experiments to production. You need to know how to present your work, how to write about it, how to make difficult tradeoffs, how to timebox and prioritize what’s most important, and how to turn customer research and quantitative data into a working solution. Most of all, you need to know how to pair up with peers like engineers and product managers who are crucial to your success.

3) The economics of product design. Usually you’re designing a product for a company. That company probably wants to make money. That means you need to understand the business impacts of the work you’re doing, and balance corporate needs with customer needs. Ideally you can build something that’s mutually beneficial for everyone, but it’s not always easy—and of course, biz performance is ultimately what pays your paycheck.

4) The customers of product design. Now back to my main point. All of the previous parts are critical for a product designer to understand deeply, but they aren’t worth a hill of beans if the designer doesn’t also have a depth of understanding about WHO they’re designing products for, and what those people are trying to accomplish.

As we learned from my unscientific Twitter poll, a lot of designers have no formal training about how humans think or make decisions, which is literally what software is all about. Software is a process of presenting people with choices, giving them tools and commands to complete tasks, and guiding their behavior in one way or another. It’s all extremely psychological. Just look at the common practice of A/B testing—this is like running Pavlovian experiments on a large anonymized population. You ring many different sounding bells for a bunch of hungry humans, and see what makes them salivate the most.

Understanding the psychology behind software design is possibly more valuable than all the other skills combined. If you know how people think and how they make decisions—often irrationally—you’ll know how to help them more effectively. You'll develop curiosity about the who and the why before you even get into designing the what and how. Then you’ll make a better product, which in turn means you’ll have a more successful business.

Yet so many designers are still winging it, learning about the behavioral impacts of their work on the fly, or deferring to research partners to bring all the answers. This surely results in poorly designed products, makes businesses less efficient, and causes inadvertent harm on customers who have to suffer with the consequences of ignorant design.

I don't have any great solutions for this, but the root cause feels like lacking educational options for anyone looking to do software development. We're all cobbling our knowledge together through imprecise college curriculums, bootcamps, and self-taught random learning on the job. It makes the whole field extra inaccessible and difficult to master.

Have you seen examples of holistic or thoughtful software curriculums? I'd love to hear about them. Hit me up on Twitter or by email.

“Should designers code?” is an obsolete debate

November 7, 2021

I entered my software design career with a hybrid computer science and art background, so my creative process has always been programmatic. For nearly 20 years my medium of choice was the web, where I taught myself to to build my own stuff, first with plain HTML, then with CSS, then PHP, JavaScript, Rails, and all sorts of other tools along the way. Later on I dipped into building native apps with Swift.

I've long thought that this hybrid code/design approach was the ideal way to do software design, at least in the sense of deeply understanding all the core materials you're working with, so you can make informed choices.

Designing programmatically also has a number of productivity benefits, the best of which is that it's easy to make computers do a lot of annoying detail work for you. There's no need to spend time toiling over hypothetical mockups of interfaces, when you can just work directly on the actual interface in the actual codebase.

This is especially useful when you're working with large datasets and iterating on little details in bulk, like adjusting a visual element that will reappear 50x on a page. It's easier to change a couple lines of CSS than to update 50 separate parts in a mockup. You can immediately see the effects of the change, and then continue tweaking until you're happy, with no need to communicate all your pedantic nitpicks to a programmer. Commit the code and you're good!

BUT.

This year I started working at Twitter, which is a larger organization than I've ever experienced before. At Twitter, I'm not writing any code. I'm working with other designers in Figma, using a collection of neatly developed components from the company's design system.

I'm certainly a little less speedy, because I'm not a Figma pro yet. I also occasionally find myself yearning for a few of the advantages of programming.

But otherwise, I'm surprisingly happy with the new process…for two reasons.

Creative tools for designing interfaces are as sophisticated as they've ever been. Figma is built specifically for this purpose, so you can be fast and productive in maximum fidelity.
I realized that software design is not really about code at all. Code is just the material outcome of your design process, and a set of constraints that you need to consider throughout that process. Knowing programming does help you understand those constraints, but you can also achieve that by partnering closely with developers instead.

A designer's main job is a nested puzzle: identifying the right problems to solve, figuring out the right solutions to those problems, persuading lots of people that you did it all correctly, and then finally putting a well-built product in customers’ hands.

In a larger organization where systems are complex and there are dozens of different teams working on projects, the designer's role is more focused on communicating internally than on designing final production designs externally. You need to do the latter too, of course, but it's a fraction of the total design work you're churning out.

Most of your design work is in explorations, ideas, research, and presentations that help you collaborate with lots of stakeholders. Larger orgs necessarily have specialists focused on all the finer points of the work. They’re thoughtful and methodical in making changes.

In this scenario, the company is incentivized to make it fast and convenient for designers to churn out high quality, realistic mockups without having to dip into code. The speed of systemizing your UI like this is remarkable. Using the design system, we can spin up almost-production-quality comps in an afternoon, then distribute that for feedback right away.

And what’s more, the real-time features in Figma create a healthy collaborative space for lots of people to explore and review ideas simultaneously. It’s amazing and feels like a tool from the future.

At this point, the age-old “should designers code?” debate is mostly irrelevant. Designers should do whatever they need to do to make things happen, in whatever circumstances they’re in.

If you enjoy writing code, and you work at a company that wants you to write code, then yes you should. (You should also demand a raise, because you're doing two jobs, and it's truly difficult to be good at both things.)

If you don’t enjoy writing code, or you work at a place that doesn't require it, then don’t do it.

Both of these situations are good and fine. You do you. Don’t listen to anyone who tells you you’re wrong for whichever choice you made. 💞

How to keep your work and personal computing separate

November 6, 2021

Earlier this year I unexpectedly left a job I’d been doing for a long time, and I learned a lot from that experience. One of the sillier but important lessons is that mixing my work and personal data on the same computer was an absolutely terrible idea.

Obviously there are tons of advantages to just using one computer. One device is much simpler, and everything is always right where you need it.

But there are so many downsides I didn’t fully appreciate:

When you change jobs, it’s stressful and urgent work to split things back apart.
If your employer supplied your computer, they have some degree of control or ownership over it, so your personal data is at risk of being monitored or leaked (and vice-versa).
With no work/personal separation, it’s trivially easy for one to spill into the other. In my case, I would always check in with work stuff during off hours, because it was right there in front of me.

None of that is healthy!

Since the job change, I’ve made it a point to steadfastly, stubbornly keep my computing lives fully separate, with as little overlap as possible.

The problem is, how do you manage using multiple devices without turning your daily life into a constant sysadmin hellscape? And perhaps more importantly, how do you do this in a world where all communication and conveniences are linked to cloud accounts that follow you around?

There are a bunch of different ways to solve this, most of which are inelegant in some way, but here’s what I’ve done.

Two laptops. One for work, one for home. The work one is for 8-5 only, the home one is for any hours other than that. I don’t use them simultaneously.
A good desk & monitor that’s easy to dock. I have an LG 27” 5K display that hooks up to a Mac (which I leave in clamshell mode) with a single USB-C Thunderbolt cable. Along with that, I use a Keychron K6 keyboard and a Magic Trackpad. I can plug my work or home computer into this setup, and it works great.

Pro tip: if you’re in the market for one of those LG displays, get one on eBay instead. The retail price is bananas.
An iPad with a nice keyboard case. This is my personal hub while I’m working during the day. You could use a phone or a second computer instead, but the iPad is really ideal because a) it takes up barely any desk space, and typing on it is still quite comfortable, b) it’s powerful enough with multitasking, c) it feels perfect and fun as a little dedicated control panel for things.
I use an 11” iPad Air with a Smart Folio Keyboard. I run Messages and email in side-by-side mode, and I also use it to control Spotify and other environmental home stuff while I’m working. This way, any non-work-related notifications that pop up are still in sight.
Note: it would be great to use just one keyboard for both the iPad and work Mac, but I haven’t found a solution for that. My Keychron has multi-device Bluetooth support, but toggling between devices is laggy enough to be annoying and error prone. (I’m deathly afraid of typing a message meant for my family into work Slack!) Two keyboards is just safer and easier.
Two separate iCloud accounts. Personal iCloud is on the iPad and the home laptop. Another iCloud account is on the work laptop, in case I need something from the App Store or whatever.
Separate 1Password vaults, with a handful of items copied to both vaults. Work passwords and personal passwords shouldn’t (and can’t) mix in this scenario, but there are a handful of things you may need to access regardless of context, like benefits websites, financial accounts, and pay stubs. So those few passwords get manually copied to both places.
Separate headphones. This is a pain, but AirPods don’t seem to work well across different iCloud accounts. It’s easier to have two sets.
Work email, calendar, and Slack on my personal phone. This is arguably a major breach of my hardcore separation philosophy, but not being able to see or respond to messages from your phone is kinda busted in 2021, so it’s all on there.
I did still maintain some separation though: my work stuff is in the standard Gmail and Google Calendar apps, with notifications off. Personal stuff is in Spark and Fantastical. No shared apps.
No personal data on the work computer. None. At all. I don’t even read personal email in a browser tab.
Airdrop or Dropbox for getting things across the work/personal divide, on the rare occasion you need to. File sharing is probably the most annoying aspect of this arrangement (for example uploading a screenshot from your phone to your work computer) but Airdrop works fine most of the time.

So that’s how I’m doing this, and it’s pretty smooth!

I also asked people on Twitter for suggestions, and as you might expect, the answers were all over the place. Here are a few more ideas, if you’re not into the iPad/Mac split.

Logitech Flow to use two computers side by side simultaneously.
A wired KVM switch, with trackpad and keyboard in wired mode, so they toggle properly (Bluetooth switching doesn’t really work well for this.)
Dual-booting separate isolated operating systems, so you can boot into work mode or home mode individually.
Different work/personal user accounts on the same machine.

A recipe for design job searching & interviewing

September 5, 2021

Greetings, fellow design job seeker! If you're feeling rusty or uncertain about how to succeed in finding a new role, this is a writeup for you.

A few months ago I left my job of almost 10 years, and landed rather dramatically into a job market that I didn't know how to navigate. To figure it out, I interviewed with a lot of companies and learned on the fly.

Having gone through all of that, I came away with some hard-earned knowledge about the process. There's a recurring set of ingredients and steps you need to take for any job you want, just like a recipe. Imagine you're a restaurant chef and you have to prep a four course meal for the company that might hire you. Read through the steps below and you’ll have a good sense of how it usually goes.

Note: this writeup is tuned for senior level designers and design managers, but most of this will still apply if you're just starting out, or in an engineering/product role.

Also note: these suggestions are mainly about applying at mid-size, public companies that have a formal hiring pipeline. If you’re applying for startups, there will be a lot less fanfare. If you’re applying for a mega company like Google, there might be even more fanfare.

Step 1: Kitchen prep

Before you get into any job search, you're going to need some ingredients. Collect an inventory of your past work (hopefully you have this saved somewhere), reflect on everything you've done so far, and consider what you'd like to do next. Think about your personal principles and values, what aspects of work you enjoy and what you dislike, and your areas for growth in your next role.

Growth might mean doing more of the same work at a higher level, working on different problems that you haven't tried before, or switching into a new role/context entirely.

Lastly, think about how much money you hope to make, and generally what type of company seems appealing right now. The specifics are up to you, but you'll need to have a coherent explanation of your future interests, so be honest with yourself, get settled on a general direction, and write it down somewhere. You’ll need to know what you want, and you’ll need to be able to explain it to people.

Step 2: Set the menu

Now it's time to create an up-to-date portfolio and resumé that reflects what you've been up to. This is hard work. I spent many weeks building this website, which contains a deep dive into my projects, writing, and general philosophy as a designer.

You likely don't need something so in-depth. A one-page site with some personal background and a few work samples is probably the minimum, just make sure it communicates where you've been and where you hope to go next. You can also use a publishing tool like Notion, Craft, or Polywork if you don't want to do something super custom.

The portfolio, philosophy, and resumé are necessary but not sufficient aspects of the job search process. They're like line items on our dinner menu: they help set expectations for what you're offering, so hiring teams can make an initial judgement about you. If you're selling hamburgers, you're not going to attract companies hankering for tacos.

Step 3: Open the doors

OK, we're finally ready to start letting companies in to our restaurant. That means we have to go out and tell them we're open for business.

There are several ways to do that:

Announce that you're on the market, using whatever social networks you're on. I've found Twitter to be the best platform for design/tech folks, but use whatever works for you. Job searching is the primary time that LinkedIn is actually useful, so get your business suit on and go for it.

Regardless of what network you use, be extremely clear about how you want people to contact you: open up your DMs, share your email address, or set up a contact form. Ask people to retweet or boost your announcement for reach.
Tap in to your personal/whisper networks if you have those. Reach out to former colleagues and friends, holler in Slack channels, text people, just ask around. You might find out about upcoming openings that aren't published yet, or get some direct contacts for companies you’re interested in. Don’t be afraid to ask people for access to whisper networks, either.
Look at job boards and submit applications for openings at companies that seem like a good match. You already have the materials from Steps 1 and 2, so this won't be too tough, but make sure you tailor any application to the company/job description, rather than just sending in a generic form letter. Show the company you care about THIS specific job.

Important: quadruple-check that you have no typos or grammatical errors in your application! You don't want to disqualify yourself just because you misspelled the company’s name. This sounds ridiculous, but it happens a lot more often than you’d think.

Here are a few friendly job boards I like:

Ease into all of this slowly at first, and see if you get any responses. You can always blast-apply for all the roles you’re interested in, but if you get calls for several of them, it might be overwhelming.

Once you start applying, you should take notes on everything you're doing. Keep track of companies you've applied to, save links to the job descriptions, contact info, notes, compensation info, and anything else you want to track. You’ll also need Google Calendar, since almost everyone uses this to schedule interviews and calls. Make sure you have a system for tracking all of this in advance. I just used Tot for taking notes and Fantastical for events.

Step 4: Appetizers

Hopefully soon you’ll get callbacks or interest from some companies. Most of the time, you'll start by having a ~30 minute phone call with a recruiter. This is like an appetizer, just a warm-up to the main course.

They'll explain a bit about the company and the role, and you'll need to re-tell the same information from Step 1: your work experience, interests, and future goals again. Be sure to contextualize your answers around the job you're actually applying for, so if it's a design systems job, you’ll need to talk in more detail about your design systems experience.

The bar you’re trying to clear is proving you have basic competence and qualifications, and that you don’t seem like an asshole in some way.

Also prepare to talk about compensation expectations. Sometimes recruiters will ask, sometimes they won't. If they don't, it's fine to bring it up, but some folks will be cagey about money discussions until you've made it through more interview rounds. The main goal at this early stage is to make sure you're not way off. If you expect 150k and the role is going to top out at 100k, both parties shouldn't waste each other's time.

There are varying opinions about how to do the early compensation chat. Some people recommend never saying a number, and others claim you should definitely say a number. Here's what I found worked well:

Recruiter: Do you have a target for compensation?

Me: I'm pretty flexible. Do you have a general range you're expecting for this role?

Usually they'll state a conservative estimate, which is like the floor you would expect for the lowest-level entry into the position. You can probably expect the ceiling to be ~20% more than whatever they quote.

BTW: recruiters are legally not allowed to ask what you've been paid in the past, so it's your choice if offering that info would give you some leverage or not.

If you’re interviewing at a publicly traded company that offers equity (stock) as part of the compensation package, you need to know a lot of technical details about how that works. Check out the addendum at the end of this post for an explainer. You should have a good understanding of this before you talk to the recruiter, otherwise they’ll be speaking gibberish, and you’ll have to nod your head agreeably while desperately Googling info about stock grants. Let’s just say I learned this the hard way, lol.

One other note about compensation. Most companies will quote some combination of the following parts:

Salary
Signing bonus (usually a fixed number)
Annual bonus (usually 10-30% of your salary)
Equity (in many forms: RSUs, ESOPs, profit sharing)

You’ll get quoted a "total compensation" number, which is a projected sum of all those bits combined. Not all companies offer all those bits, either. You might get an annual bonus but not signing, or equity but no bonuses.

Regardless of the specifics, keep in mind that salary is the only guaranteed money. Everything else is subject to some amount of risk or variance. Bonuses may or may not be granted in full. Equity can range from useless to life-changing, depending on how the circumstances play out. It’s up to you to decide what blend you want, and what your risk tolerance is, but the safe bet is to optimize for salary first.

Step 5: First course

The next step after talking to a recruiter is typically a 1:1 call with the hiring manager (the person who will be your manager if you get hired.)

This is a more serious interview than the recruiter chat, but just barely. It’s mostly a “get to know you” call where the manager can go into more depth about the job, and learn about your background and interests. Get ready to repeat your story from Step 1 again! See why we needed to nail that down?

This is a perfect opening to get a stronger sense of the company and their motivation for hiring. The only reason companies hire people is because they’re struggling in some aspect, and they’re aspiring to make progress in a new way. So the hiring manager will usually be candid about that.

Like any good first course, it should be a great opening: not too light and not too heavy. Everyone should walk away from the conversation feeling good, with some positive energy to continue. If not, this will be the end of the line. Don’t feel bad about closing up shop if you're not feeling it. Just tell them you’re exploring other opportunities instead.

Step 6: Main course

If everything went well in the previous step, your recruiter will let you know they’d like to proceed. At this point the process may fork in a few ways:

A more rigorous interview or 1:1 presentation with the same hiring manager or a small group. You’ll present some past work, and talk about your skillset and experience in greater detail.
A series of “onsite” interviews. This is sort of a holdover from the days when a company would fly you in to their office and spend 8 hours with you in various intro meetings with stakeholders. In a remote context, it’s basically the same, just over Zoom instead.
A work assessment, either with a live pairing code/design session, or a take-home project you’ll complete over a designated period of time.

Option 2 is the most common, usually also with the presentation from 1, and occasionally ALSO requiring something like 3.

This phase is the hardest. It’s a lot of work. In most cases you’re looking at a 1-2 day commitment to presenting and being periodically grilled in interviews with cross-functional peers, like engineers and product folks. Not to mention all the prep time leading up to that.

That means it’s gut check time. You should be enthusiastic about this opportunity, if you’re going to take so much of your time and the company’s time. You don’t want to find yourself in a long series of grueling interviews when your heart isn’t in it, so make sure this is something you seriously want before you commit. Double check reviews on Glassdoor and Blind to get a sense of the company’s pros and cons—but take these with a grain of salt. They’re about as trustworthy as product reviews on Amazon.

The process will be exhausting for sure, but it’s also the primary opportunity for you to glean if you like this company and this team. The people you meet, their priorities, and their sensibilities will all become apparent. Remember that you’re interviewing them too. You should enjoy talking to them.

You’ll also get a sense of how organized the company is. Scheduling interview rounds with many participants is tough. There will be a lot of back and forth about times and dates. Some meetings will inevitably get rescheduled a few times. Your recruiter will prep you for whatever you’re expected to do, so you’ll know roughly what they're looking for.

You also have to make a presentation! These usually run about 45 minutes. If you're presenting remotely, you'll need to pipe your presentation into a Zoom or Google Meet screenshare, and then tell your story to a group of observers who have their mics muted and their video turned off. It’s a weird experience, sort of like just shouting into a cave and hoping people are hearing you.

Take about 10 minutes to introduce yourself, sharing your story and background (yet again), and then spend the remaining 30 minutes on case studies and showing some past projects. These ought to be tailored to the job you’re trying to get, so you’ll need a library of case studies to draw from.

In the case studies, focus on how you solved a type of problem rather than just showing generic design work. Your portfolio already gave everyone the big picture, so now focus in on some specifics. Show a case study where you overcame an engineering roadblock, or where you had a novel idea and persuaded the team to go for it. Any relevant examples that demonstrate your ability to get things done in the face of the many adversities of design work.

Also make it clear precisely what your role was in the work you did. Were you leading the project or executing someone else’s vision? How much of the final product did you produce?

For more advice on prepping a great portfolio presentation, check out this post from Brian Lovin.

After the presentation, you'll meet in smaller interview rounds with one or two people at a time. Show up to these interviews with a set of questions to ask. Here are a few that I asked almost everyone:

What’s the design culture like at your company?

How are product teams organized, and what’s the overall size and work process?

How is your work/life balance, and how has that changed over time?

How do you feel about this company’s transition to remote work?

What are the challenges you’re facing as a group right now?

What do you think success looks like for someone in this role?

What was your experience onboarding as a new employee at the company?

Are most of your projects product-driven, design-driven, engineering, or a mix? Who has the final say when there's a disagreement?

What’s coming up next for the company? Do you feel it’s in a healthy place, growing, positive initiatives, etc.?

At the end of all of this, you will be tired, so don’t pack several of these interview rounds into a single week unless you’re intentionally trying to sync up multiple offers.

Step 7: Dessert

Alright, you made it! The main course is heavy, but the finisher is hopefully sweet. A few days will go by, and then your recruiter will reach out with a decision to make an offer or not.

If not, don’t despair. Remember that this is a process of finding the right mutual fit. If the company decided to go in another direction, that's good for you too. You should join a company that’s eager to have you, because that’s where you’ll do your best work! It’s always valuable practice to go through an interview round—you’ll get better at it every time.

It’s also common for a company to discover they want to hire you, but not for the exact role you interviewed for. Be prepared to take a little detour along the way, and if that happens, it will prolong your timing somewhat.

But whenever you do get an offer, CONGRATS! It’s time to move on to the last step.

Step 8: The nightcap

Not all meals require a nightcap, but this has been a damn marathon, so a cup of coffee is in order.

Your recruiter will probably call you, and then inform you about the company’s intention to make an offer. This verbal conversation is a good time to settle any terms that you were uncertain about leading up to this point, and ask questions. If you’ve had a money conversation already, this is the time to ask for a bump to the high end of the range you expect.

Reagardless of your previous conversations, you should almost always ask for more money*. Why? Because the worst case scenario is that they’ll say no. In all other scenarios, you will get more money. So ask! Remember, the company has also invested a ton of time into interviewing you, so they’ll probably try to approve any reasonable requests.

The key word there is “reasonable.” You can’t realistically expect a place to 2x the number they quoted you originally, so don’t ask for something too extreme, or you'll run the risk of pissing them off. But you can certainly ask for a salary bump or whatever else feels fair, especially if you can justify it based on your prior experience.

*One caveat: don’t bother asking for more money if the company has a publicly published, transparent salary system. In that case it's probably not going to be negotiable because the company has standardized compensation for every role and level. Buffer is an example of this.

You should also have a start date in mind. Here’s my advice: the interim time between getting a job and starting the job is one of the sweetest tiny breaks in life. It's a moment to rest, relax, and know that you have something interesting to look forward to. So if you can, kick that start date a few extra weeks out, and take a little vacation.

The recruiter will need to get approval for all of this before making a written offer, so expect a couple of days of waiting.

Step 9: Settling the bill

It’s finally closing time at the restaurant. All that’s left now is agreeing to the terms, signing on many dotted lines and getting contracts settled. Nothing is official until it’s all on paper, so make sure you review the contracts thoroughly. If you need a carveout for side projects, don’t forget to report that. If you have any other changes, now’s the time.

You should also look closely at the benefits packages and make sure you understand everything. Double-check the 401k match if there is one, the health plans, vision, dental, wellness benefits, vacation time / PTO, and anything else the company offers.

Depending on the company's hiring rigor, there might be several more steps here, like doing a background check, verifying your past employment, contacting references, and ordering equipment.

Addendum 1: Making a decision when you’re considering more than one job

You might find yourself with several companies or offers you’re interested in. This is a good problem to have, but it can be difficult to figure out which option is the best fit.

The decision comes down to what makes sense on paper and what feels right. For the paper part, make a spreadsheet to cross-compare the practical details of each job, using these categories as columns:

Role/Level
Total Comp (estimate)
Salary
Signing Bonus
Annual Bonus
Equity
ESPP (discount/cap)
Vacation
Health Benefit
401k

For the feel part, try rating the options in these qualitiative categories:

Reputation
Job Fit
Vibe
Work/Life Balance
Future Outlook

This way you can visualize all the different aspects of the jobs you’re considering, and potentially rule out or down-rank the ones that aren’t working for you.

Addendum 2: WTF are RSUs?

MAJOR DISCLAIMER: I'm not a financial specialist, so the following explanation is just what I've learned trying to understand this for myself. Definitely do more research and make sure you fully grok these terms before you negotiate any compensation package. This is just a brief explainer of the major things you need to know.

RSU stands for Restricted Stock Unit. These are stock shares that a publicly traded company may grant to you, as part of your compensation agreement. It's "restricted" because you must work at the company for a certain amount of time before you're granted any shares.

Here's an example of an RSU agreement a company might offer:

"$400,000 in RSUs over a 4-year vesting period, with a one-year cliff, and annual refreshers."

Let's break this into human words:

If you work at the company for 4 years, you'll get the entire RSU grant. If you quit or get fired before that, you won't get the whole amount. 4 years is when you're fully vested.
You have to work at the company for at least 1 full year in order to get any stock at all. This is why it's called a "cliff." If you leave before the first year is up, you get zilch.
After the first year, you'll be granted 25% of your total amount. After year two, you'll get another 25%, and so on. In our example, after the one-year cliff, you'll get 25% of $400,000, or $100,000. Some companies use a different vesting schedule, like monthly or quarterly, so make sure you're clear on this. Once some portion of your grant is vested, you'll be able to sell the shares.
A "refresher" is an additional bit of stock that the company may grant on top of your original RSU agreement. Let's say you have the $400,000 agreement. A refresher would be some extra amount (maybe $25,000) added every year after the first year. This ensures you’ll still continue to get some stock annually if you stay at the company past the 4-year term of the base RSU agreement. Some refreshers also have a compounding factor, such that the refresher amount gets higher the longer you stay.

That's the basic explanation, but there’s a lot more to this. You should check out these detailed explanations to get a complete understanding, and be sure to dig into tax implications too:

If you made it this far, way to go! You’ve become a business professional!

I hope this little recipe was helpful for you. If you have any more advice or important things I missed, send me an email and let me know.

Thanks for reading, and best of luck!

P.S. shout out to Unsplash for all the silly stock photos of food stuff. Also shout out to the Haha Business guy for being so good at businessing.

P.P.S. I originally sent an early draft of this post to my newsletter. If you'd like exclusive access to my various brain ramblings, including at least one pun per month, subscribe below.

The eternal challenge of making one UI do two things

August 18, 2021

Recently Twitter launched a nice design refresh, and one of the changes was particularly controversial. The Follow button's styling was visually reversed from its previous design:

I’m convinced this was a mistake because I don’t think anyone would intentionally do something like this. It’s like turning on the lights when they are off. Obviously makes no sense. I bet it will be fixed ASAP.
[Before vs after:] pic.twitter.com/g6mY9ukTvV
— Rasmus Andersson (@rsms) August 15, 2021

On the surface this just looks like a styling change, but there’s a related bit of complexity lurking here that I wanted to point out…

Buttons that also show a status are always difficult to get right.

Why is this?

Most of the time a button is a one-way action. You see a button, you click it to do the thing it says, and you’re done. Here’s an example from ye olde days:

There’s no question what’s going on there. Either you’re OK with this or you Cancel. Regardless of which option you pick, this dialog and the buttons go away entirely, and you’re done with this decision.

Two-way buttons

By contrast, when a button represents the state of data stored in a system (like whether you’re following someone on Twitter or not) it’s also doing the work of a checkbox — turning a binary flag on or off — and submitting the change simultaneously.

So, what you really have is a checkbox and a submit button munged together. A fully extrapolated version of this UI might look like so:

Obviously, this takes up a lot more space than a single button, which is why designers end up making the compressed version.

I’m not sure if there’s a name for a munged checkbox-button, so I'm just going to call it a CHECKBUTTON.

There’s no universally accepted design pattern for checkbuttons, so there’s no perfectly right or wrong way to go about making one. Here are a bunch of examples of how one might design the two states of a Follow checkbutton:

Notice that you can style these however you want!

Furthermore, the language is not really ideal in any of them. “Following” isn’t an action word, it just explains the state. You have to infer that clicking the button will unfollow.

But “Unfollow” has a negative connotation that isn’t great either. Imagine clicking Follow and then having the button immediately say Unfollow. Sure it’s an accurate explanation of what will happen, but it’s also a little harsh, since you just made the choice to follow. And of course, any platform wants to encourage you to follow, not unfollow people.

Either word choice is a slight compromise, which is probably why the web version of Twitter has a THIRD state that says Unfollow when you hover the button:

This all gets even more complicated when you’re working with a design system. Design systems usually have a notion of primary and secondary button styles, which help differentiate the main actions on a screen from supplemental ones. The primary button style is more visually dominant.

With a checkbutton, you have to figure out how to map these styles onto the state of the data. Should it be…

ON=PRIMARY OFF=SECONDARY

ON=SECONDARY OFF=PRIMARY

???

The styling you choose depends on: 1) the button’s default state (on or off), 2) whether this is an action you want to visually emphasize, and 3) all the other buttons you have to contend with on the same screen. The choices are subjective and context-specific.

In Twitter’s case, the controversy over the change was due to swapping the styles people were already used to. Dann Petty shared an excellent explanation of how the new styling changes make sense when you look at them holistically, and in context with other buttons in the app.

In conclusion, designing checkbuttons is as clear as mud. I’ve personally been tripped up designing these at least half a dozen times. They almost always end up causing an internal design debate over the styling and word choices, so it’s not surprising to see this cause a stir in public too.

Have you seen any particularly good examples of a checkbutton? Hit me up on Twitter or by email and I’ll tack them on to this post.

Reviewing the Safari redesign in iOS 15

August 8, 2021

I've been running the iOS 15 beta releases on my iPhone, and the most noticeable change is a major redesign of the core UI in Safari. Apple has been iterating on this in the open, so I thought it might be fun to write up a little critique, as if I was working on this feature and trying to decide if it's production-ready or not.

Note: this post is about iOS 15 beta 4. It will probably be out of date after more betas ship.

What's new?

Here's a side-by-side comparison of Safari in iOS 14 and in iOS 15 beta 4, using Pitchfork as an example website with the content mostly blocked out, so you can see the differences. Pitchfork has its own bottom-oriented menu which gets into the mix here.

The summary of changes is as follows:

All UI for interacting with web pages has been moved from the top of the screen to the bottom.
Safari's top and bottom toolbars are now combined into a single floating URL bar, which is elevated above the page content.
Swiping the URL bar left or right moves between tabs.
Safari now supports tab groups, and has a whole new tab management interface.

Pros & cons

There are a few direct benefits to the new design:

Changing web pages is easier to reach.
Swiping between tabs is handy.
Tab management is significantly improved.
The new UI is unique and interesting!

There are also several downsides:

The floating URL bar sometimes feels "in the way." It's visually dominant in a way that the old design was not. This is because a floating element requires extra empty space above and below it, so it draws more visual attention than something anchored to an edge of the screen. It's also located in the space where you're commonly scrolling or tapping on things.
Formerly quick interactions have become fiddly or more complicated. Toggling to private browsing mode is especially clunky, now requiring multiple taps inside the new tab group options.
The buttons around the URL field are crammed tightly together and easy to accidentally tap. The URL itself is also substantially truncated to make space for all the buttons.
The bottom of the screen is now rather overloaded. The iOS home bar and Safari's URL bar are in close proximity with each other, such that swiping in the wrong spot can give you an unintended result. This is compounded even worse with websites like Pitchfork that have a bottom-oriented navigation design — you now have 3 different bottom navigations vying for attention (website, Safari URL bar, iOS home bar.)

Why are they changing this?

I'm all for experimenting with new ways to tackle an old UI problem. You'll never know if you can find a better design unless you try.

When you're redesigning something as fundamental as browser UI, you have to start with a strong opinion about what you're trying to improve. It's tough to beat time-tested, production software that everyone is used to, so you have to define what aspects you think could be better, and explore new designs with those targets in mind.

We don't know what Apple's priorities are, but it seems like they're trying to optimize for three things:

Reachability, so it's less of hand-stretch to interact with the browser's UI.
Saving space & decluttering, so the browser has less of its own chrome and more room for showing web content.
Uniqueness. I'm not sure if this is an explicit intention or just a side effect of designing for the first two.

Let's assess how well this new design hits the mark.

Reachability is improved for accessing Safari's URL input, but this also has a detrimental side effect on the reachability of website content. Website menus and navigational elements are often positioned up at the top of the screen. Top-oriented browser chrome helps push those elements vertically lower, so they're easier to reach. Without any browser chrome at the top, content is even further away from your hand, and thus harder to reach.

This is a significant drawback because 80% of the time in a browser, you're interacting with websites, not the web browser's UI itself. As a result, the overall reachability benefits of the new design are mixed.

Space saving is one of those designery goals that's often more rooted in extreme minimalism than in actual real-world use cases. I'd guess that no customer has ever complained about the space Safari's UI used up in iOS versions 1-14, because that space was occupied by several useful buttons and inputs, and it wasn't too much space anyway. It worked fine, and most people just don't care about this.

But as a designer, it's a worthy principle to let content be the star of the show as much as you can. If it's possible to get away with less browser chrome, and to have simpler interface, why not give it a shot?

So let's imagine we're giving it a shot. A great way to start is by collecting all of the various UI elements, and combining them into one place. This is like organizing your socks by putting them all together in one pile, and then figuring out how to subdivide after that.

That's what Apple has done here. Two distinct toolbars have merged into one toolbar.

The designer’s reason to do this is to aggressively oversimplify — cut out almost all the UI — and then make each individual affordance fight for its reintroduction to a prominent placement. This is an iterative process of paring everything back to the barest essentials, and then gradually reintroducing features that prove themselves to be so vital that they're too annoying to have tucked away in a secondary location.

As you can see in those screenshots, several buttons have been moved into the Share and Tabs submenus, rather than being prominently accessible all the time. Reader mode and Bookmarks didn't make the cut. The Reload button is now much smaller, and the Forward button only appears conditionally.

Uniqueness is also a designer goal that doesn't have an immediately obvious end-user impact, but it can have a lot of upside over time. If Apple decides to run with this new UI, Safari will have a standout interface that looks nothing like any other mobile web browser. That means it'll be easier to tell Safari apart from the others.

If Apple gets it right, they'll lead the industry with something new and weird, and other browser makers will likely end up following suit. This will subsequently affect how mobile website creators design their sites. And new innovations will also find their way into this bottom-oriented UI ecosystem over time.

All of this is why it’s worthwhile to try redesigning "solved problems" like browser UI. In the end, you might arrive somewhere better—or at least somewhere different.

Is the new design a success?

It depends on how you measure success. Based on our goals listed above, the new design is probably successful enough: it’s (somewhat) reachable, space saving, and unique.

But is it a significantly better experience overall?

So far, not really.

Generally, software is easier to use when affordances are prominent and visible, rather than buried away in submenus. Of course, you can’t make everything prominent and visible because there’s only so much space, so you have to prioritize things. There are three main choices for every input or button you need to include:

CLEAR AND OBVIOUS: The affordance is visible and prominent, and it has an icon and textual label describing its function.
OBVIOUS, BUT NOT CLEAR: The affordance is visible, but it has an icon without a text label, so users have to guess what the icon means.
CLEAR, BUT NOT OBVIOUS: The affordance is minimized or hidden in submenus. Users have to hunt around or guess where to find it, but once they find it, it's clearly labeled.

In complex software there are lots of affordances to organize, so you usually end up doing all three of these. The overall goal is to make the essentials as obvious and clear as you can, and then tuck away the more esoteric or less-frequently-used options.

With the Safari redesign, Apple has demoted several buttons into the NOT OBVIOUS category, and the ones that remain are all packed together. There are now at least five different affordances in that one small bar, which feels crowded and a bit unresolved. Some features, like private tabs, are deeply buried and probably don’t need to be.

In total, the new design still has more day-to-day friction than the old version it replaces. But it's not too far off, and Apple might decide that some increased friction is worth the tradeoff for all the other benefits outlined above.

What would I try next?

This depends on how committed the team is to the floating URL bar design. If they've locked on to this concept, all that's left is optimizing and polishing it as much as possible. No matter what, the floating bar is always going to feel a little clunky or crammed, because you simply can’t pack much more into one horizontal bar.

Whenever I'm feeling space-constrained in a design, I start questioning why we've backed ourselves into a situation where we don't have enough space to work with. So if the team still has time to try something else, I would suggest relenting on the ultra-minimal bar and explore other designs that would allow for more flexibility again.

For example, they might try something that works more like the Maps app's sliding bottom panel. With that pattern, you could keep most of the minimalism and reachability benefits of the floating bar, but with a lot more room for quickly showing secondary options.

Here's a rough mockup showing how that could look:

This is less minimal for sure, but also a bit more obvious and not as space-constrained. The challenge with this design would be how to present the tab management UI (should it go underneath the sliding panel, inside of it, or on top?)

Edit: Matt Birchler also had this thought and mocked up a nice variation too!

Anyway, I hope you enjoyed this little armchair design critique. It's difficult to change this sort of thing, especially when you're designing out in the open and getting tons of feedback from all over (especially rando designers writing on their blogs. 😅) Looking forward to seeing the final solution.

Update!

In iOS 15 beta 6, Apple shipped a new version of this interface that’s much closer to my mockup above. They also added an option to switch back to having a top-oriented URL bar if you prefer that.

I’ve been using this for a day, and it feels like a good compromise between the original iOS 14 design and the new floating URL bar concept. You might argue that designing in the open scared Apple’s designers from taking a bigger risk, but I think the feedback led to a much less jarring, more usable variation that still accomplishes all the goals above. It’s a great example of taking feedback and polishing an idea to be production-ready.

Staying vulnerable

May 16, 2021

I believe that any creative pursuit—whether it’s art, design, music, poetry, or whatever else—requires willful vulnerability. Interrogating the world around you, facing things you’re scared of, learning about other people’s struggles, internalizing all of that, digging deep within yourself, and using your experience and compassion to make something positive.

This means lowering your defenses. Reckoning with hard questions that challenge you. Having the humility and willingness to see through someone else’s eyes. Feeling their pain and joy as strongly as your own. Identifying your weaknesses and working to improve them. Using your station to lift others, even when it means putting yourself at risk.

It goes without saying that this is difficult and counterintuitive. You will be overwhelmed sometimes. It takes careful discipline and strength to stay leveled and keep going.

But you have to try. You have open yourself up, in order to affect change outside of yourself. There’s no other choice. These are the keys that unlock meaningful creativity, and a meaningful life.

Stay open, stay vulnerable. For good.

This website stinks

May 8, 2021

Is there any project worse than making a website for yourself?

That wasn't a rhetorical question. The answer is NO, there is almost nothing worse. The project requirements are garbage and the client nitpicks everything.

In my many years of working on the web, I’ve created dozens of personal sites, ranging from a basic single page to an exhaustive library of all my past creative work. And I was always unhappy with whatever decisions I made on every single one of them.

A designer working on their own site

I’ve finally realized that’s just the reality of making a personal site. It will never be satisfying, because there’s always something else you want to try: another color scheme or typeface that might work well, a new piece of tech you could experiment with, or a different way to present yourself entirely.

That’s why, this time around, I decided to focus on storytelling.

Most design portfolio sites are just the bare minimum, a few pictures on a website. I want to see more portfolios with some narrative and statement of intent—where someone came from, what they believe in, and some honest, plainly written explanations of their past work.

This stuff is important! If you don't tell your story, no one else will.

I’m tired of having my story scattered on other people’s platforms. Bringing it all together, and seeing it all in one place, forced me to reckon with what I’ve done, and begin to see and where I should go next.

I hope it’s a helpful example for some folks out there. Thanks for stopping by!

(P.S. I will admit, there is one thing I like about this site: the error page.)

Surviving through creative low points

April 9, 2021

The past couple of weeks have been tough, for no specific reason. I've been generally unfocused and lacking confidence. I haven't been as productive as usual, and I don't have an exact explanation for it.

For me, this sort of thing is cyclical. I've been through it enough to recognize when it's happening. Sometimes I'm riding high and cranking stuff out, and other times I'm very much not. I know that both situations are fleeting, and both will pass.

Everyone has highs and lows, of course. But it's harder to work through the lows when your job requires continual creative output, substantial amounts of compassion & empathy for others, or the self-confidence to make decisions and take risks. It's like trying to win a prize fight on an empty stomach, you just don't have the right energy.

It can be tempting to think of this phase as a sort of burnout mode, and take time away to recharge. Oddly, I've found that's usually even worse for my mental and emotional state. If I hit one of these low points and just bail for a while, I'll continue to dwell on it the whole time I'm supposedly "resting." Like I ran away from my problems rather than sorting them out. It just prolongs the feeling of being stuck, and then adds a dose of guilt and ongoing self-doubt.

My trick for getting through a lull is this: pick any uncontroversial, stupidly easy things to do, and just focus on those for a while. Notch any successes, regardless of how small or mundane. Fix one bug. Mop the floor. Organize the sock drawer. Make a list. Whatever you can do mindlessly, without having to question your decisions on some existential level.

Eventually, enough of those small successes add up to the feeling that you did something, and you don't feel so doubtful anymore.

Build yourself a little step stool out of the mud, until it's tall enough to climb all the way out.

Software gardening and death

March 3, 2021

This is grandpa's orchid. Grandpa was an avid gardener, and he kept a batch of lively orchids in his basement. When he passed away a few years ago, most of them didn't survive in his absence. We retrieved this one, and now we take care of it.

Software is a bit like this house plant: its wellbeing depends on the folks who constantly tend it. Without us around, it gradually erodes.

The app Weather Line recently announced it'll shut down soon, after 9 years of service. Some customers who recently purchased lifetime subscriptions are upset, because they only got a few months or years of use out of it.

But in software, “lifetime” doesn’t mean a human lifetime, or even the lifetime of a whole business. It only represents the creator's commitment to tending something.

When you buy a lifetime subscription, you’re buying into someone’s garden. They’ll keep sending you radishes as long as they’re in the dirt. Hopefully for a good long while, but who knows.

When you think about it this way, software is not such a technical thing. It’s a human thing. Buying an app is also buying a relationship with the people who make it.

When modern software dies, it leaves no trace. It's fully gone, obliterated from existence entirely. Folks usually react to the death of software like a bad breakup, with pain, shock, anger, and overreaction. “That software I used for 5 years, and those people who made it, they’re over! Screw them! I’m switching apps right now.”

These aren’t just lost apps and deleted bits. They’re also lost relationships. Human connections permanently severed. It’s surprisingly emotional, and stings for a while.

This also explains why people mourn dead software, long after it’s gone. Google Reader is still sorely missed. The loss of Rdio cuts deep for a legion of devotees (myself included.) Not just because these tools were unique and empowering, but because the people who made them imbued their creativity and thoughtfulness directly into the products. The soul and energy is irreplaceable. You can’t just switch to an alternative and recreate that.

Sometimes, thinking about the end of things helps you reflect on what you’re taking for granted. That’s why I wrote this post. There are a lot of great people making beautiful things and tending their gardens. And we’re amazingly fortunate to have access to more of those than any other time in human history.

Keep on gardening, and cherish your friendly gardeners. 🌸

How money dictates design decisions

February 23, 2021

Lately I've been thinking a lot about how products get started.

As a designer, there's one important choice you have to make at the beginning of a project, which sets the stage for every other decision you'll ever make…

💰💰💰 How you'll make money. 💰💰💰

That's it. That's the only thing that matters. Your entire future, and every single one of your design choices, will be forever defined by this one decision.

Let's say you're making a new email service. You could charge your users directly, and build a business from that revenue. Since your users are your customers, everything you design is for them—you have to convince them this product is worth paying for, so you'll focus on solving their problems and improving their lives.

Or, you might decide to make an email service like Gmail: free for everyone to use, but backed by ad revenue. In this case, your users are merely a trojan horse for making money. You need them to use the product constantly, in order for the advertising and growth numbers to pay back.

These two approaches completely change how you tackle the same design problems.

The first approach is about empowering people.

The second approach is about capturing people.

In HEY, we tackled one of the worst problems with email: everyone gets way too damn much of it! So we created The Screener. You decide who's allowed to email you, so your email volume is dramatically reduced by design. You end up checking your email less often than you did before.

But in Gmail, Google's financial incentives are all about MORE email. Because…

More email = More clicks = More views = More time spent = More ad revenue. 💸

So, although Gmail could add a Screener feature (and maybe they eventually will due to social pressures), it would be in direct opposition to their business incentives.

This is also how you get a whole cottage industry of email marketers tracking your interactions. When the most popular email platforms are already tracking you themselves, what's a little more tracking on top of that? It's tracking all the way down. Everyone gets a slice of the sweet sweet data pie.

This may all seem dead obvious by now, but to reiterate: the only products that have your back are the ones you pay for.

If you're currently using a service that either...

Doesn't have a business model yet, or
Has an ad-based business model

...your attention and data are being abused in some way.

Think we've all already learned that lesson, after more than a decade of destruction by the likes of Facebook, YouTube, and more?

We absolutely have not! Right now, the new darling of social media, Clubhouse, is financially backed by the same old venture capital gang at Andreessen Horowitz. It's experiencing fast growth, and it currently has no declared business model at all. (Though there's some chatter about some sort of Patreon-style payment system.)

Also not too surprisingly, Clubhouse is already doing problematic things with your contacts and data. Sound familiar?

Any company that "doesn't have a business model yet" actually has a business model—they just haven't said it out loud. They're gambling that they can give away a service for free, grow it to absurd usage numbers, and then turn on the money faucet later, through ads, acquisitions, or some other approach.

It's the same story every time. And we all keep falling for it.

As a designer, ignoring that early decision about making money leads you to make harmful product choices, like casually abusing everyone's contact data. Because you don't have to think too much about protecting your customers. You prioritize growth first.

As the famous Sinclair quote goes, it's difficult to get a person to understand something, when their salary depends on not understanding it.

If you want to know the underlying truth about a product, just look at how it's funded. That's all you need to know.

Achieving “simple design”

July 8, 2020

Yesterday I got an email asking how we came up with simple designs for Basecamp and HEY, so I thought I’d share the answer here.

At a high level it boils down to a handful of foundational principles that affect the decisions we made:

Always choosing clarity over being slick or fancy. We aim to make the UI totally obvious and self explanatory, by keeping individual screens pared down to the essentials, showing only one focused thing at a time, and so on. Good product design eliminates the need for an instruction manual!
Caring about copywriting, and taking the time and space to explain things with words, instead of making minimalist UIs with lots of unlabeled buttons, etc. (Although we’re still guilty of having a few of those.)
Prioritizing respectful interfaces that don’t overwhelm or try to nag the user into certain behaviors. We intentionally don’t include things like notification counts/badges, 3-column designs, or other distracting elements unless we absolutely can’t avoid them. We don’t like the idea of having “sticky” interfaces—we want our customers to use our products to get the job done, and then go do something else. That makes the whole design approach more peaceful in general.
Having a strong editorial sensibility, and knowing when to split complex concepts into simpler individual parts. This one is more of an art than a science, but we have a strong instinct for breaking down problems until they can be easily understood in simple UI flows.

There’s one other thing that’s important for simple design. It’s not merely a matter of having clear or basic-looking interfaces. (It’s easy to make a simple UI that doesn’t really do much.)

The magic combo is having simple interfaces paired with powerful capabilities below the surface. For example, HEY looks simple, and it’s straightforward to use, but it’s backed by some deeply considered ideas, logic, and machinery that reduces the effort in keeping up with email. The interface itself is simple, but the thinking and the system behind it is complex. The product is valuable because it saves people time and anxiety dealing with the terrible email mess that they had just learned to live with.

This was originally posted on Signal vs. Noise.

How to focus in an open office

August 22, 2019

@ Quartz

Nobody really owns product work

June 12, 2019

A few years ago I helped design the search feature for Basecamp. We’d invented a unique Mad Libs-style interface, and I was rather fond of how it turned out.

About six months later, other folks at the company had a new idea for the search UI, and they replaced my design with a completely different version. The new version was much faster to use, and worked better in every way, but I was still slightly bummed that my original design was erased out of existence.

Fast forward a couple years later.

We’ve been working on lots of new stuff lately, and many of my prototype concepts have already been obliterated or mutated several times over by other teams with better ideas.

But now, I’m finding that process to be exciting and exhilarating, instead of disheartening!

What changed?

Somewhere along the line I realized and accepted the truth: nobody really owns anything in a product made by a team.

Whatever ownership you have over an individual contribution is immediately forfeited the moment you commit the code. At that moment, the work becomes part of the ever-evolving organism that comprises a software system.

Each piece of work is like a pebble tossed into a river. Maybe your pebble will become bedrock—sticking around for a long time and altering the water’s trajectory. Or, maybe it’ll quickly dissolve into dust when new pebbles come along and crash into it. Both of those outcomes are completely natural and worthy of celebration.

In this way, collaborative software work is egalitarian. It doesn’t matter who did what, as long as the team is collectively accomplishing something greater than any one person could have done alone.

(This also goes for people with the title Product Owner. They don’t actually own the whole product or any of its component parts. They just own accountability for decisions about what to build and when.)

Once you realize this basic truth, you can separate yourself emotionally from the work you’ve done. But this is easy to say and hard to do, because it’s so counterintuitive! How can you be deeply, personally invested in making something, and then immediately stop caring about it when you’re finished?

The trick is to change how you evaluate forward progress: the long-term survival of your own contributions is irrelevant. The important thing is that the product is evolving into the best version your team can create together.

The more you appreciate the power of the group over the individual, the sooner you’ll become a more effective collaborator. You’ll be more willing to hear and absorb others’ viewpoints. You’ll be more eager to seek out everyone’s best ideas, instead of digging in and defending your own. And you’ll be able to celebrate other people’s achievements with authenticity instead of territorial resentment.

This also requires self-confidence, which is especially difficult to come by when you’re early in your career and trying to prove yourself. Imposter syndrome is a powerful beast.

Here are a few ways I’ve talked myself out of moments of weakness.

Since my work got changed later, does that mean I did a bad job? Usually not. If your project got shipped, and you completed it on time, and everyone was satisfied with the work, it met all the requirements it needed to meet at that moment. That’s great.

If my ideas didn’t get traction, should I just stop speaking up? No, keep trying! Often the right idea is built upon many not-quite-right-ideas. Suggesting the wrong thing can quickly lead to discovering the right thing.

How can I be sure I’m having an impact, when my work didn’t last for the long haul? Measure your work against what came before it, not what came after it. In my case, I designed Search v1, which later got replaced by Search v2. But what came before Search v1? LITERALLY NOTHING. We made a giant leap forward by building and shipping that foundation, and then we improved on that foundation later. That’s successful impact!

Our monkey brains are weird, so even with this rationale, you might never be able to completely eliminate that moment of gut-reactive sadness when something you created is overwritten. That’s OK. Just appreciate the journey you’ve been on, look ahead to future destinations, and it’ll subside quickly enough. ✨

This was originally posted on Signal vs. Noise.

The right amount of perfect

January 31, 2019

Everybody knows that perfect is the enemy of good, but it’s one of those tenets that’s easy to say and hard to live by. When you’re working on a creative project, there’s almost always something you wanted to do better, or some little detail that didn’t quite live up to your standards. That can be tough to accept.

This is why thoughtful project scoping and timeboxing is so important: if you don’t have a structured process and an end date for your work, you’ll be more likely to wander out into the perfectionist weeds. The farther out you get, the more time you’ve spent—mostly for diminishing returns.

But even with a structure in place, there’s still another tricky aspect of perfectionism: what perfect means for one project doesn’t necessarily apply in the same way to another. You have to redefine your standards every time.

Here’s an example.

Right now we’re working on some new stuff. It’s in the very early stages, so our level of tolerance for imperfections should be very high. We’re in the figuring-things-out phase, NOT the production-quality product phase.

So what’s the problem?

We’re extremely good at making production-quality software! Maybe a little too good. Our natural temptation is to apply our usual rigorous development practices to the new stuff we’re exploring.

You don’t need so much rigor, early on. You need only the right amount of perfect. What that means depends entirely on your situation.

When you’re inventing something from scratch…

…the right amount of perfect is an ugly sketch with a Sharpie marker. Or some hardly-formed daydreams, haphazardly pecked into a notes app.

When you’re making a prototype of an idea…

…the right amount of perfect is a barely-working demo. Can you show the idea to someone, well enough to demonstrate how it should work—even if it’s stitched together with duct tape and popsicle sticks?

When you’re building something new…

…the right amount of perfect is “basically functional.” You need to use this new thing to learn and keep iterating, so it has to work fundamentally. But it certainly doesn’t have to be polished. It can be clunky. It can have lots of bugs. It can have unfinished parts. At this stage, finishing everything to a high level of perfection is a waste of time, because you might throw out half the work along the way. You need just enough perfect to be able to make judgements and improvements, but no more than that.

Finally, when you’re certain your idea has legs…

…and you’re committing to going for it, that’s when you can swing back around and make it fully considered, polished, and complete. This is the moment for production-quality rigor. Full speed ahead. Get those high standards back in action!

Transitioning between those phases is tumultuous, but it helps to clearly define which phase of a project you’re in, and what the expectations are for what you’re making. (You can do that formally or informally.)

My trick is to repeatedly ask myself, “How fancy does this need to be, for right now?” The answer is usually: NOT SO FANCY. This is a helpful gut check that helps you pull back from overdoing something.

Consider full perfection a luxury you can indulge when you have nothing else more significant to worry about. For most teams, and most projects, that happens exactly 0% of the time. 😅

This was originally posted on Signal vs. Noise.

Working in quality time instead of clock time

October 9, 2018

One of the things I love about flexible remote work is the freedom to step away from something whenever I need to.

Right now I’m exploring designs for a new product idea. R&D work like this depends on having good mental and emotional energy. Sometimes you have it, sometimes you don’t.

When you’re energetic and motivated, great things happen spontaneously, in unpredictable bursts of inspiration.

But when you’re tired, distracted, or in the weeds on something, it’s usually better to stop working. Just admit (temporary) defeat and give yourself a chance to regroup. Do something else that’s less taxing, or call it quits and start again later.

I always find this difficult to do, because the working world tells us that full-time employees should put in 8+ consecutive hours no matter what. So what if you’re frustrated, burned out, or not making much progress? Too bad, gotta punch the clock! Back to the grind! Grind it out!

The problem is, grinding it out is counterproductive for creative work, because creativity doesn’t happen on a linear time scale. Forcing it usually makes things worse. If you drain your human gas tank all the way to empty, you’ll get even more burned out. And then your bad mood and low energy spills over to another workday, prolonging the creative drought.

Don’t do that! Walk away instead, and leave it for your future, better self to look at with fresh eyes.

Then start thinking about productivity in terms of quality time instead of clock time. You might end up making the same progress with only 20 energetic hours that you would have made in 60 tired hours.

Once you get in the habit of that, you can optimize your schedule around your own energy and enthusiasm. I’m usually at my creative peak in the mid-morning and lose steam after lunch, so I shuffle my work accordingly. I do exploratory freeform stuff in the morning, and I save routine tasks (like implementing something I already know how to do) for the afternoon. I also have a rather short attention span, so I take tiny breaks a lot.

Your schedule might be the opposite. But whatever it is, give yourself the freedom to go with the flow, or shut off the flow altogether. Some days suck and you have to cut your losses. Other times you just need to walk away for 20 minutes to get a flash of inspiration.

The key is to be self-aware and completely flexible about time. Dump the clock. You’ll be much happier and more effective, and your work will still get done in the end.

This was originally posted on Signal vs. Noise.

How you’re being manipulated by software

September 17, 2018

The Book of Life (1898)

There’s a term we use in software design called the happy path. It describes a best-case scenario, in which customers use a product exactly as intended, without bumping into any edge cases or uncommon problems. This includes the interface you see when you sign up, setup steps you have to complete, and so on.

For software designers, a happy path is also an extremely powerful psychological tool that allows us to control people’s behavior and direct them to do whatever we want.

If that sounds surprising—and slightly terrifying—think about how many times you’ve blown past a lengthy software license agreement and clicked the Agree button without looking.

Were you thinking deeply about what you were doing?

Probably not. And you’re not alone! Research shows that humans have a natural aversion to decision making. As Smashing Magazine describes it, people simply don’t like to make choices unless they have to:

Making an explicit decision requires effort, after all. Time, thought and consideration are often required to determine the best choice. It turns out that people are remarkably sensitive (and averse) to the amount of effort that making a choice demands.

And therein lies the trouble.

If you pay close attention, you’ll notice something else about software happy paths. Like a tell in a poker game, they subtly reveal a company’s underlying motives.

Since designers know you’ll probably avoid making difficult decisions, they can take advantage of your passivity and coax you into doing anything they want.

For example, if you’ve ever installed the Facebook Messenger app, you were likely encouraged to continuously upload all of your phone’s contacts to the service. This is framed as a way to help you text people quickly.

Look at that screen for a moment. There’s no opt out button! You can only choose OK or Learn More.

And who wants to Learn More when they’re signing up for a chat app? Almost nobody.

I’m guessing at least 80% of Facebook’s users just tap OK and move along immediately. There’s even a little animated arrow encouraging you to tap OK, in case you momentarily considered doing something else.

But let’s say you’re among the 20% that happens to pick the Learn More button. You’ll get a cutesy second screen:

This screen finally has an opt-out button, in plain text, buried underneath some copy that vaguely implies you’re wrong for questioning any of this.

What’s more, Facebook’s designers neglected to mention a rather important detail: continuously uploading your contacts helps them collect a ton of data about people who aren’t even on Facebook.

Tapping that OK button is a trivially small decision. It takes just one minuscule tap of your finger. It’s done in less than a second.

But the impact is quite large indeed! You’re implicitly agreeing to send Facebook little bits of info about everyone you know. Now imagine the network effects when you multiply that by the millions or billions of users who also tapped OK in the blink of an eye.

This little happy path is feeding a massive data beast, which probably has details about almost everyone on Earth. And Facebook had ample space — two separate screens! — in which to mention anything about this.

So why didn’t they?

Because endless growth and data collection is the foundation of their business, and that necessitates doing invasive things to their users.

They need you to feed the beast, and they certainly don’t want you to think about it. So they use cartoon animals and sneaky happy paths to make sure you stay blissfully unaware.

Using software is inherently a handshake agreement between you and the service provider. It’s not unlike paying for a physical service.

The problem is, many of the dominant software makers are abusing your handshake in increasingly dastardly ways. They treat their customers like sitting ducks — just a bunch of data points waiting to be harvested. And when growth slows, they resort to deceptive tactics to keep the trend lines pointing skyward.

So what can we do, as consumers?

First, keep your eye out for sneaky manipulation, especially when you’re first signing up for a service. If you’re asked to share personal information or forced to commit to something that makes you feel uncomfortable, you’re probably being used.

Second, slow down and thoroughly consider the choices you’re making. You’ll end up discovering weird, surprising things about services that you thought were harmless.

Third, be wary of any “free” software platforms. Sure, you’re not giving those companies any money directly. Instead, you’re giving them something else they’ll use to get money — your attention, your time, your personal information—all things that are arguably more valuable than money.

And finally, pay for software! When you pay real money to software creators, you’re supporting them, and they’ll support you in return.

More and more independent software makers are standing up and defending users against data misuse and manipulation. Recently, Feedbin significantly altered their tech to protect their users from being tracked. That’s a great example, and there are many others like it.

Vote with your wallet, and support the people who really do have your back.

This was originally posted on Signal vs. Noise.

Software is breaking our brains and businesses

March 12, 2018

…and it doesn't have to be this way.

An ode to experimental design

February 23, 2018

If you search the Internet to learn about A/B testing, you’ll find scads of articles bursting with tips for cranking your business performance into the stratosphere.

You’ll get blazing hot secrets like…

BOOST YOUR CONVERSION RATE BY 300% WITH THIS TINY TWEAK

and…

DESTROY YOUR COMPETITION USING A STATISTICALLY SIGNIFICANT SHADE OF BLUE

…and it just keeps going like that, into an overenthusiastic pit of armchair psychology.

As the gurus tell it, A/B testing is like Vegas slots: plunk some crap into a machine, score a handful of 🍒🍒🍒s, and voilà, Easy Bake Revenue!

With a pitch like that, who could resist? It sounds so simple. If you don’t do it, you’re obviously a fool who’s leaving money on the table.

Welp, I have a couple of hard truths for ya:

It’s not as easy as it sounds, and those big gains aren’t such a sure thing.
Setting out to dramatically boost some arbitrary metric (signups, conversions, revenue, whatever) is the wrong way to approach a design problem.

How do I know this?

I spent most of last year testing dozens of conversion-related design ideas, and I found that the jacked-up performance aspect is the least interesting part of the process, by far.

The most interesting part is how it can change your thinking. It energizes your adventurous spirit, introduces you to uncharted territory, and lands you in cool places you never expected to go.

Here’s what I learned, and why I’ve come to love doing experimental design.

Testing turns your designs into trash.

After running tests for a while, you’ll find yourself throwing away mountains of design work for just a handful of meaningful improvements.

Do that enough, and you’ll notice something: Maybe design isn’t such a special endeavor after all!

The truth is…a lot of design is ephemeral, malleable, disposable…garbage.

Anything you make today merely represents one moment in time. Maybe it’s your best idea now, but it’s not necessarily the best idea you’ll have in another two days or two months.

Testing makes this painfully obvious on a shorter time scale. You’ll soon become less emotionally invested in your precious creations, and more focused on the problems you care about.

Testing strengthens your gusto.

I don’t know about you, but it took me years to build up the confidence to make hard design decisions. I still struggle with it sometimes.

You have to succeed and fail a lot. You have to take criticism a lot. And you have to trust your gut and keep at it, day after day.

Experimentation is a great way to build that muscle. It’s an opportunity to try things you aren’t completely sure about, and gives you a sweet little safety net for failures.

Testing makes you thoughtful.

It can be tempting to do experiments like the lottery: throw a bunch of random shit at the wall and then declare victory when one thing performed best by random chance.

You might get lucky a few times that way, but it’s a terrible long-term approach. Without some overarching vision, you’ll be left with a gnarly mess of test results born from guesses, and no clear plan for what to do next.

The better way, of course, is to start with good ideas! Do some research, come up with educated hypotheses and concepts you believe in, then build and test them to verify your thinking instead of defining it.

Testing destroys perfectionism.

It’s so freeing to ship a bare-bones version of an idea because it’s “just a test” that you’ll either improve or throw away when it’s done.

If you thought that same design had to stick around permanently, you’d probably never launch it with a lot of known flaws or incomplete parts. You’d want to fix up every last detail and make everything perfect first.

Amazingly, those rough, imperfect tests often outperform the supposedly perfected version you already had in place. When you see that, you’ll realize your outsized attention to detail might not matter as much as you thought.

A license for imperfection is an extremely useful defense against Fussy Designer disease. We should all be vaccinated early and often.

Testing builds empathy.

This sounds counterintuitive: running an experiment is mostly a pragmatic and statistical kind of thing. How is that related to empathy?

It’s related because you’re forced to learn what happens when real human people interact with your work. Your choices all have directly measurable effects, so you can’t hide behind bullshitty designerspeak or vague justifications when the data shows you’re just flat wrong.

That means you have to get outside your insular designer bubble, stop thinking of people as numbers, and get in their shoes a bit.

When you do that, the business boosts you want will happen as a natural side effect of continually tuning your product to serve your customers’ real-life situations. Making things clearer or more efficient for your customers always pays off.

Testing helps you make space.

One tough challenge in UI design is making physical space for new things you want to do. There’s only so much room on a screen!

You might have ideas that require injecting steps into an existing UI flow, adding more screens, revising a visual hierarchy, or rearranging certain navigational elements.

Doing stuff like that is a gamble. You might be confident that your new version is better in some way, but are you sure your improvements are worth the extra steps or added complexity?

Testing lets you dip your toes in the water. You can run a short experiment and see if you’re busting your business before committing to a direction.

Testing tells the truth.

The truth is weird. Sometimes common sense wins out. Sometimes a wild idea succeeds. Sometimes a version you hated performs the best. Sometimes your favorite design turns out to be a total stinker.

Where else in the design world can you get opinion-free feedback like this? There are no Art Directors or Product Managers or App Store reviewers telling you what they think is right. It’s real human nature telling you what’s right!

It’s a fascinating, powerful, bizarre reality.

This was originally posted on Signal vs. Noise.

The mortality and joy of productivity

December 13, 2017

Illustration via The British Library

“How much time left until I’m dead?”

I try not to think about that question, but yet, it’s always there, hidden away in my mind’s attic, nestled alongside all the other intentionally suppressed memories, which, despite my best efforts to keep them stowed, tend to stubbornly reappear in my subconscious against my will.

I’d better get to work.

Work staves off my feelings of helplessness against the unstoppable march of time. I’ll get some work done and feel accomplished. I’m using my time wisely after all. Not frittering and twittering away my precious minutes.

In a modern life where stillness is rarified and busyness is glorified, the scarce moments of downtime feel like a neglectful mistake. The guilt washes over you, thinking of what you might have gotten done, what greatness you could have accomplished, instead of this vague nothingness.

And so, we all shove and squeeze more tasks into a life that can’t be filled any fuller. We deny our limitations and remain convinced of our inefficiencies.

We seek out tricks to get faster.

We hack our lives,
and hack our bodies,
and hack our kids,
and hack every last second
until we’ve hacked our brains
into believing we accomplished something meaningful.

At some primordial level we’re all optimizing for time, running down our own clocks, whether we can bear to admit it or not. Time is all we have, and we never have enough.

So we pray at the altar of productivity, lusting for the promise of extra free time that never seems to come — which is probably for the best, since we wouldn’t know what to do with it if we had some.

I’d better get to work.

I sit down to build a software tool that helps people get their work done. I find happiness in this process, knowing that I’m using my valuable time so others can reclaim some of theirs.

Maybe I’ll save them a few minutes a day.

A few minutes they didn’t have to spend on something mundane.

A few minutes to breathe.

My work is real, but it’s also ephemeral. It exists in a transitory state until it, too, reaches its end of life: bits and bytes unceremoniously overwritten and replaced by the next new version.

Most traces of my work will not survive me. I know this because a large percentage of it is already gone, obsoleted and obliterated by time and progress.

There’s a comfort in this. Obsolescence is freedom. Freedom from past decisions, past mistakes, past victories.

My work has no past, and my work has no future.

So why am I like everyone else — obsessed with working more, working better, working faster?

I think it’s the joy of it. Feeding the unrelenting creative fire that burns fast and hot. Finding a thrill in the unknown. Taking a chance on something new. Hiding from my mortality inside a perpetual state of forward motion.

Maybe we’ve got it all wrong. Productivity in this life doesn’t have to be about optimizing time. It could be about optimizing joy. Packing the most joy into each moment.

That’s a productive pursuit.

I’d better get to work.

This post was originally written for The Human in the Machine.

Move slowly and fix things

November 14, 2017

Synoptic Table of Physiognomic Traits

Recently I took a monthlong sabbatical from my job as a product designer.

When you take 30 days away from work, you have a lot of time and headspace that’s normally used up. Inevitably you start to reflect on your life.

And so, I pondered what the hell I’m doing with mine. What does it mean to be a software designer in 2018, compared to when I first began my weird career in the early 2000s?

The answer is weighing on me.

As software continues to invade our lives in surreptitious ways, the social and ethical implications are increasingly significant.

Our work is HEAVY and it’s getting heavier all the time. I think a lot of designers haven’t deeply considered this, and they don’t appreciate the real-life effects of the work they’re doing.

Here’s a little example. About 10 years ago, Twitter looked like so:

Twitter circa 2007

How cute was that? If you weren’t paying attention back then, Twitter was kind of a joke. It was a silly viral app where people wrote about their dog or their ham sandwich.

Today, things are a bit different. Twitter became the megaphone for the leader of the free world, who uses it to broadcast his every whim. It’s also the world’s best source for real-time news, and it’s full of abuse problems.

That’s a massive sea change! And it all happened in only 10 years.

Do you think the creators of that little 2007 status-sharing concept knew this is where they’d end up, just a decade later?

Seems like they didn’t:

People can’t decide whether Twitter is the next YouTube, or the digital equivalent of a hula hoop. To those who think it’s frivolous, Evan Williams responds: “Whoever said that things have to be useful?”

Twitter: Is Brevity The Next Big Thing? (Newsweek, April 2007)

Considering these beginnings, is it any surprise that Twitter has struggled at running a massive, serious global communications platform, which now affects the world order?

That’s not what they originally built. It grew into something else, and now they’re not quite sure how to handle it.

I’m not picking on Twitter in particular, but its trajectory illustrates a systemic challenge.

Designers and programmers are great at inventing software. We obsess over every aspect of that process: the tech we use, our methodology, the way it looks, and how it performs.

Unfortunately we’re not nearly as obsessed with what happens after that, when people integrate our products into the real world. They use our stuff and it takes on a life of its own. Then we move on to making the next thing. We’re builders, not sociologists.

This approach wasn’t a problem when apps were mostly isolated tools people used to manage spreadsheets or send emails. Small products with small impacts.

But now most software is so much more than that. It listens to us. It goes everywhere we go. It tracks everything we do. It has our fingerprints. Our heart rate. Our money. Our location. Our face. It’s the primary way we communicate our thoughts and feelings to our friends and family.

It’s deeply personal and ingrained into every aspect of our lives. It commands our gaze more and more every day.

We’ve rapidly ceded an enormous amount of trust to software, under the hazy guise of forward progress and personal convenience. And since software is constantly evolving—one small point release at a time—each new breach of trust or privacy feels relatively small and easy to justify.

Oh, they’ll just have my location. Oh, they’ll just have my identity. Oh, they’ll just have an always-on microphone in the room.

Most software products are owned and operated by corporations, whose business interests often contradict their users’ interests. Even small, harmless-looking apps might be harvesting data about you and selling it.

And that’s not even counting the army of machine learning bots that will soon be unleashed to make decisions for us.

It all sounds like an Orwellian dystopia when you write it out like this, but this is not fiction. It’s the real truth.

A scene from WALL-E, or the actual software industry in 2018?

See what I mean by HEAVY? Is this what we signed up for, when we embarked on a career in tech?

15 years ago, it was a slightly different story. The Internet was a nascent and bizarre wild west, and it had an egalitarian vibe. It was exciting and aspirational — you’d get paid to make cool things in a fast-moving industry, paired with the hippie notion that design can change the world.

Well, that motto was right on the money. There’s just one part we forgot: change can have a dark side too.

If you’re a designer, ask yourself this question…

Is your work helpful or harmful?

You might have optimistically deluded yourself into believing it’s always helpful because you’re a nice person, and design is a noble-seeming endeavor, and you have good intentions.

But let’s be brutally honest for a minute.

If you’re designing sticky features that are meant to maximize the time people spend using your product instead of doing something else in their life, is that helpful?

If you’re trying to inflate the number of people on your platform so you can report corporate growth to your shareholders, is that helpful?

If your business model depends on using dark patterns or deceptive marketing to con users into clicking on advertising, is that helpful?

If you’re trying to replace meaningful human culture with automated tech, is that helpful?

If your business collects and sells personal data about people, is that helpful?

If your company is striving to dominate an industry by any means necessary, is that helpful?

If you do those things…

Are you even a Designer at all?

Or are you a glorified Huckster—a puffed-up propaganda artist with a fancy job title in an open-plan office?

Whether we choose to recognize it or not, designers have both the authority and the responsibility to prevent our products from becoming needlessly invasive, addictive, dishonest, or harmful. We can continue to pretend this is someone else’s job, but it’s not. It’s our job.

We’re the first line of defense to protect people’s privacy, safety, and sanity. In many, many cases we’re failing at that right now.

If the past 20 years of tech represent the Move Fast and Break Things era, now it’s time to slow down and take stock of what’s broken. The world needs as much care and conscience as we can muster. Defend your users against anti-patterns and shady business practices. Raise your hand and object to harmful design ideas. Call out bad stuff when you see it. Thoughtfully reflect on what you’re sending out into the world every day.

The stakes are high and they’ll keep getting higher. Let’s get to work.

This was originally posted on Signal vs. Noise.

The unnecessary fragmentation of design jobs

March 28, 2017

Photo by Sanwal Deen

Hey there, tech designer person. Have you noticed the increasing number of vague specializations we’ve invented for ourselves?

Here are a few I grabbed from a job board 10 minutes ago.

UX Designer UX/UI Designer UI Designer Graphic Designer (UX & UI focus) Visual Designer Digital Designer Product Designer Presentation Designer Front End Designer Web Designer

Bleh. What’s the difference between UX and UX/UI and UI? Isn’t Product also UX/UI? Isn’t a Front End a UI? What’s a Graphic Designer with UX & UI Focus? And isn’t all of this Visual/Digital design?

For an outsider, the differences are extremely subtle. I’ve been talking to a lot of industry newcomers lately, and they’re almost unanimously confused. They’re struggling to gain the right experience and make portfolios to match our foggy job definitions.

Even worse, the companies hiring seem equally puzzled. One designer told me he took a UX job at a startup, and then his new boss asked him to explain what UX is about — after he had already been hired to do it!

UX AND UI, WHY OH WHY

This must be happening because everyone can barely keep up with the demand for design work. Companies are racing to fill seats and execute hastily-defined design processes without bothering to question if it’s all necessary for their particular business.

If your company does that, you might find yourself in a game of Designer Hot Potato like this one:

Bob’s good at customer research, so he’s on UX. He’ll make some personas and get a bunch of post-it notes on the wall right away.

Then we’ll get everyone together to look at the post-its and move them around.

Then we’ll write down ideas and ask Natalie to make wireframes. She’s our UX/UI person.

Then she’ll hand those over to Beth, our UI designer, who’s good at turning wireframes into a high fidelity UI mockup.

Then Beth will hand that over to Steven, our Front End person, to make a prototype.

Then we’ll try it to figure out what we did wrong, and check back with Bob on the post-its again. TO THE POST-ITS!!!

This is surely good for 3M’s office supplies revenue, but as a creative process it sounds painful to me.

I’ve never had a job quite like that.

For much of my career, I was a lone wolf — the only designery person at a small business or government org—so I had to figure everything out myself. I had to talk to people, learn about the problems they were having, come up with ideas, create a good-looking solution, write words, and build the UI piece of the final product.

It was tough, and it took years of practice to become competent at any of it. But I loved the diversity of the work and the exciting potential for new discoveries.

Recently John Maeda’s Design in Tech Report suggested a name for my kind of role: Computational Designer.

These computational designers exist in a hazy middle ground — not quite pure engineers, not quite pure designers — but their hybrid status is increasingly attractive to technology companies. …The most successful designers will be those who can work with intangible materials — code, words, and voice. (via WIRED)

I dig this idea, but I don’t think we even need the word “Computational.” I think the software industry has been overthinking this, and what John describes is just Design.

Design (with a capital D)

I believe Design requires a holistic grasp of problems, potential, and materials.

If you’re only focused on examining problems, you’re not empowered to dream up the proper solutions.

If you’re only dreaming up what you could do, you’re not close enough to the ground-level truth.

If you’re only working on the nitty gritty implementation, you know about the what but not a lot about the why.

A capital-D Designer is comfortable working organically across all of that, without needing to slice it up into separate little steps and responsibilities.

This is possible in the real world

That’s exactly how great small teams work. They skip most of the formal process stuff, and have Designers do everything: writing, visuals, code, project management, whatever it takes.

Think this sounds too hard? Like there’s no way you could possibly be good at all of that?

Take a step back for a second. We’re only talking about making software.

Yes it’s hard…but in the grand scheme of things it’s not THAT hard.

If you’re not convinced, take a look at Art. Lebedev Studio:

Founded in Moscow in 1995, Art. Lebedev Studio is the only design company in the world offering product design, city and environmental design, graphic design, websites, interfaces, packaging, typeface design, custom patterns and book publishing under one roof.

That’s a lot of stuff! Projects across mediums, genres, industries, you name it. No artificial limits on anything. Inventing things using whatever materials and means necessary.

And that’s not even a new idea. Now look at Raymond Loewy, born in 1893:

Raymond Loewy (November 5, 1893—July 14, 1986) was an industrial designer who achieved fame for the magnitude of his design efforts across a variety of industries. Among his designs were the Shell, Exxon, TWA and BP logos, the Greyhound bus, the Coca-Cola bottle, the Lucky Strike package, Coldspot refrigerators, Studebaker cars, and the Air Force One airplane. He was involved with numerous railroad and locomotive designs. His career spanned seven decades.

Some of Raymond’s logos

A seven decade career making not just logos and products, but planes, trains, and automobiles too! Here’s Raymond, by the way:

Raymond Loewy, one hell of a cool Designer.

So if Art Lebedev’s shop can do all that, and Raymond Loewy could do what he did, why are we so insufferably particular about boxing ourselves into tiny little specialties just to make websites and apps?

Imagine if we stopped doing that, and tossed out our process assumptions and self-defeating arguments about what should be one person’s responsibility versus someone else’s.

Maybe we could all gain that magical holistic understanding, and grow to become Computational Designers. Or even just Designers.

You can make it happen

If you like this notion, try treating your career like your most important project. Be curious and restless. Aim to be constantly learning and trying new stuff without limits. Find a company or a work environment that lets you take a shot at everything you want to do (they’re out there!)…or invent your own little niche if you can’t find that.

This may not be the easiest career path to travel. It’s almost certainly not. But I guarantee you’ll enjoy the ride—especially since you’ve designed it yourself.

How to launch software changes without pissing people off

March 14, 2017

Software designers and developers are all about NEW. We like to experiment with far-out ideas and make shiny things. Our livelihood depends on it.

We’re so addicted to NEW that sometimes it clouds our judgment. We love NEW and everyone else should too, so we force heavy-handed product changes onto our customers without much explanation.

And if they didn’t want that? Or if they got needlessly interrupted by it?…Shhh…we’re not so interested in those problems.

Dislike Facebook’s redesign? Deal with it! Confused by the newest Windows updates? Oh well! Missing some features in the new Final Cut? Too bad, they’re gone forever!

It’s no surprise that these sorts of changes are comically unpopular:

Developers get away with this anyway because we wield all the power. We can push a button and instantly transform an experience for millions of people in one shot.

Imagine if that kind of thing happened in the real world. Let’s say this was your living room:

And one day it suddenly became like this:

You wouldn’t be cool with that at all. You’d be totally freaked out!

What!? Where are all my books? What is all this creepy stuff? Whose head is that? Are those antlers?

That’s exactly what we do to our customers all the time. No wonder they’re always ranting on Twitter.

Why do we make disruptive changes?

There are a few reasons developers decide to steamroll NEW stuff.

It’s hard for us to keep legacy tech around. It’s easier to put everyone on the newest iteration and maintain only that.
It’s hard for us to make transitions elegant. A redesigned screen or feature might be jarring, but it takes extra care to ease people into the change.
It’s hard for us to balance business interests and our users’ needs. Sometimes we need to make a big move to stay relevant in the market or help the bottom line, so we drop a bombshell update on the world — continuity be damned.

Notice a theme there? It’s hard for us. Our laziness or time constraints take over, so we pass the buck.

How we can do better

Not all changes are massively disruptive, so we just need a strategy for identifying the ones that are, and then handle them properly.

Here’s how we do it at Basecamp.

Make only additive updates and improvements.

Taking away a feature is a surefire way to upset your customers. Even if it’s something small or innocuous, you can guarantee someone depended heavily on that one thing you took away.

The solution? Don’t take things away (if you can possibly avoid it.)

Thoughtfully adding stuff is great. Who wouldn’t want more for their money?

It’s also fine to improve rough spots. Make the same features look better, work better, or get the job done faster. Nobody’s going to be bothered by that.

The don’t-remove-stuff philosophy has a strategic upside, too. If you can’t take anything away, you’ll be more conscientious about what you put in.

Take extra care when making a disruptive change.

Sometimes you have a big idea that makes your product better, but switching over will be bumpy for your existing users. In that case it’s worth the additional effort to smooth things out, even if it means extending your development budget to build transition-related features.

We did this last year when we launched some big changes in Basecamp 3. We spent a few extra weeks making a settings screen for the new features we were introducing, so we wouldn’t be shoving them down our customers’ throats. The new stuff was turned off by default, so people could opt in if they wanted to, rather than having to opt out of something they didn’t want.

Whatever extra time you spend doing this is a drop in the bucket compared to the exponentially greater time your customers might have wasted out of confusion or frustration.

Don’t bother pre-announcing changes.

You might think it’d be helpful to warn everyone before a big launch, like…

In three weeks, this website will be totally unrecognizable. You’ll have to figure everything out from scratch, but we think the new one is nicer. Enjoy!

…but what good does that do? Maybe the advance notice dulls the shock, but the customer can’t act on this information. They have to wait to be interrupted again later by the actual change.

This only prolongs the anxiety, with very little upside. It’s better to focus energy on the transition instead—make it so smooth that there’s no need for a pre-announcement.

Explain what’s different.

It’s bad enough to be forced into an update you didn’t agree to, but it’s even worse if you have no idea what happened or why things changed.

Make sure you have a way to introduce and explain what’s new when you launch, either via in-app announcements, a mailing list, a blog, or whatever method you have to communicate with customers.

People may not like the changes, but at least they won’t be blindsided. It’s the courteous thing to do.

Split distinct major versions and keep them around forever.

When we’ve collected enough new ideas to constitute a major rethink of Basecamp (this usually takes years), we create a whole new version from scratch. The previous versions live on in perpetuity in maintenance mode.

That means even there’s no disruption for people who are happily using a previous version. We incur the maintenance time and costs to keep it all running, and they keep paying us like they always did.

This might not work for some products, but it’s worked well for ours. Our customers get to keep using the version they like for as long as they want, with no pressure to do anything else. They can migrate to the newer version on their own timeline. Or not.

You’ll be glad you did

Working through these issues might not be the most fun and exciting part of your job, but it makes a big difference in how people perceive your product, your service, and your company as a whole.

A few people will always complain about any change you make. That’s life. But these approaches will help keep your support load lower and your customers happier.

This was originally posted on Signal vs. Noise.

Strategies for building a dual-platform mobile app

March 5, 2017

A few tips to help your app co-exist on iOS and Android.

The underappreciated value of incremental design

September 8, 2016

The Convair Model 118 Flying Car.

Apple announced iPhone 7 this week, and without missing a beat, the tech press decried it as dull. Tech pundits seem to have this same argument cued up every time Apple launches something that’s not game-changing innovation. I think they’re totally missing the point.

There are two ways to update an existing product:

Make a brand new version that’s unlike everything before it.
Improve it by simplifying it, making it more powerful, or adding new capabilities.

You can’t do #1 all the time. It’s just not possible. It’s a testament to Apple’s design prowess that they’ve pulled off #1 so many times, the public now expects it as a matter of routine.

Furthermore, making brand new versions all the time isn’t even necessarily good for customers. The iPhone is a stable, mature product that’s wildly popular and used by a massive number of people. Changing it dramatically every year is going to piss people off. Do you always want to relearn how your phone works every time you upgrade it? Do you always want to suffer the inevitable flaws and unforeseen bugs that arise when new moonshot stuff is launched at scale for the first time?

Sure you do, if you’re a tech reporter! But not if you’re a non-tech-obsessed human person who just wants to text their friends and check Facebook. If you’re that person, stability is a virtue, not a downside.

More importantly, there’s a critical aspect to these seemingly “mundane” product updates that people in the peanut gallery are missing:

Incremental updates help stack the deck for a big-splash release in the future.

When you have an existing product and you do want to make a big change to it, you can do that two ways:

Bite the bullet, and launch it all at once in a massive blowout release that shocks everybody.
Spread the changes out over a couple of releases that get you to the same end goal, but that aren’t as individually shocking to your customers.

In the case of iPhone 7, I believe the removal of the headphone jack is a tell that they’re doing the latter. I think whatever is coming after iPhone 7 depended on reclaiming that headphone jack space for something else. Every tiny bit of space matters!

By killing the jack in this release, they’re freeing themselves up to make a bigger move next. They knew everyone would whine and vent about that detail now. That means the next BIG launch won’t be marred by discussion about headphone jacks, because we’ll all have gotten over it by then. (People have a surprisingly short-term memory for the very strong opinions they held even a year earlier.)

The bottom line is, people get excited about changes and shiny new things, but they also hate changes — especially when they’re disruptive or different in ways that don’t seem to be a clear improvement over the old ways.

So, launching an update to an existing product is a difficult balancing act between these two extremes. Sometimes the big splash is fully warranted, but the rest of the time it’s best to be conservative and incremental. Apple’s carefully orchestrated release cadence is the perfect example of this, much to the chagrin of the overeager tech press.

Product releases are part of a larger long-term strategy, and they only make sense when you know the full picture. Only Apple knows theirs, but I’d bet on something big next time around. I suspect we won’t be bored for much longer.

This was originally posted on Signal vs. Noise.

The art of designing with heart

August 29, 2016

One of the things I love about making software is that it’s a deeply mental exercise, chock full of heady processes, abstractions, and interconnected pathways.

You can fill your brain with the practical nuts and bolts side of it—research, strategy, prototyping, programming, UI, operations, and more. Lots more.

And if that’s not enough? Indulge yourself in metrics and performance. Every last detail can be tested, quantified and optimized to the fullest. Get high on KPIs and keep your eyes on your ROI!

The problem is…with so much to think about, and so many logistics to obsess over, it’s easy to forget the reason you’re doing any of this in the first place:

🚨️ YOUR SOFTWARE EXISTS TO HELP PEOPLE! 🚨

Designers usually call this notion User Experience or Empathy. I think those names stink. They’re buzzwordy and vague enough to mean different things in different contexts.

I think we should call it what it really is: Designing With Heart.

This isn’t something that’s the responsibility of one specific team in your company, or one step in a process that you can check off. It’s a core value that informs every decision you make.

Here’s what that means in practice.

At the other end of all your strategy and metrics and tech, there are real people. Living, breathing people — who are busy dealing with their weird life, arguing with their kids, trying to figure out what’s for dinner.

When you build software, you’re painstakingly inventing a machine that stands in your place, feigns sentience, and interacts with these people on your behalf so they can accomplish something meaningful.

Your software is not just a bunch of code and UI you smushed together. It’s also a compilation of your best ideas, your best intentions, your desire to help others, your compassion, your feelings, your soul.

Your software is YOU.

(That is, if you believe in the art of it. And you should, if you give a damn about doing it right.)

When you see things in this light, you’ll notice that a lot of software is dull and lifeless.

Consider your bank’s website, or your insurance company’s billing system. They’re probably cold and impersonal. That’s because the designers treated their job as a mechanical sequence: they took a set of requirements, invented imaginary personas, wrote user stories, and sprinted their way through the work until the requirements were met. All head, no heart.

Capital One’s “sign in” page.

Now, you might think it’s fine for a bank site to be plain and transactional. After all, banking is literally a set of transactions.

But compare that to the experience you’d have with a nice bank teller (if you can still remember what that was like.) The teller smiles at you, asks how your day is going, double-checks that your math is right, offers to help with something you might have forgotten, and gives you a lollipop! 🍭

That’s a transaction with a bit of heart.

OK, so let’s say we want our software to take the place of the bank teller. That means it should ideally provide the same humane, helpful service that they did. But how?

One option is to anthropomorphize the interface and stick some personality into it, which results in UI that’s funny, folksy, clever, sarcastic, or cartoonish.

Poncho the sassy weathercat sends you messages that say “Zzz Zzzzzzz” and “Purrrrrrrrrrrrr.”

I think this only works in small doses, because humans have a low tolerance for bullshit. Unless you’re really good at it, jokey and cutesy stuff gets irritating quickly. That’s even worse than just being mechanical, because it’s a waste of time. It’s usually better to cut to the chase.

So if mechanical is bad, and excess personality is also bad…Then what’s good?

The sweet spot is right in the middle. Good software is friendly, casual, approachable — but also serious, gracious, and respectful. Just like a pleasant real-life experience you’d have at a local business.

Achieving this sounds difficult (it is) but there’s an easy trick that helps a lot.

When you’re designing something, imagine you’re sitting in a room, helping a real person with the task at hand. What would you say to them? How would you explain this screen or feature? What advice would you give? What would you tell them to do next?

Say the answers out loud, and then write down what you said. Now you’re 80% of the way there!

If you were helping someone in person, you wouldn’t be austere or formal. You wouldn’t use buzzwords or jargon or business-speak. You also wouldn’t drop HOT SARCASTIC JOKE BOMBS on them and distract them with goofy asides. You’d watch what they do, see where they get stuck, and walk them through it. You’d speak from the heart.

This common sense technique helps you see the forest for the trees. If you struggle to explain something out loud, it’s probably not clear enough. That insight leads you to ask questions like…

Can we make this interface simpler or more direct?
Can we reduce or eliminate the choices someone has to make?
Are we using natural, casual language to explain things fully?
Is this design respectful of a person’s time and attention?
Is this something I would personally enjoy using?
Did we take any shortcuts that benefit US instead of THEM?
Did we make any incorrect assumptions?

Now your design will inevitably end up clearer and friendlier. That makes your customers happier and more efficient, so they can stop fiddling with software and get back to dinner with their argumentative kids.

That should be the underlying motivation for your work. Not tech, not styling, not stats, and not money. Helping people comes first. The rest follows.

Designing With Heart doesn’t just apply to making a product, either. It can also guide your marketing, advertising, and sales work.

For example, let’s say you want to increase the number of paying customers for your product. (Who doesn’t?) That’s a business-first problem, not a people-first problem.

If you only think business-first, you might blast out canned promotional emails, or show “BUY NOW” callouts all over the place, or interrupt key workflows with interstitial popup ads.

The Wall Street Journal asks you to buy before you’ve even arrived.

These techniques may well be useful for increasing raw business performance, but they can be annoying and smarmy to customers. That’s the opposite of what we want. So how do we reconcile the difference?

Easy: think about people again!

There’s nothing inherently bad about clearly communicating the value of your product, making it easier to buy it, spreading your message to new audiences, or even asking for referrals or reviews — as long as you do so in a way that’s considerate, honest, and at the right moment.

Don’t interrupt people when they’re in the middle of something, nag them incessantly, or hard-sell them into doing what you want. If you ask for a favor, make it worth their time by thoughtfully explaining why you need their help, and perhaps offering an incentive in trade.

Follow this approach and your promotional efforts won’t just benefit you, they’ll benefit people too.

There’s one more thing you can do to Design With Heart: don’t be afraid to reveal yourself.

People develop emotional connections to other people—not machines.

When your customers can see who’s behind the curtain, and when you speak to them with honesty and authenticity, they’ll be more likely to identify with your message and approach.

Nate Kontny’s Highrise updates always have a personal touch.

If you built something because you fundamentally care about helping people, and you intend to have their back…say it! Put your name on it, tell your story, show your face, and stand behind your work. Share your real personality rather than trying to graft a fake one onto an inanimate program.

Your customers will respond in kind — and that’s the most rewarding thing of all. 💞

This was originally posted on Signal vs. Noise.

Just keep chipping away at it

July 15, 2016

Why perfection and speed may not matter as much as you think.

Why we need paid family leave in the U.S.

June 9, 2016

When you have a newborn baby, your home life descends into temporary chaos. There’s crying and messes and strange liquids everywhere, plus doctor appointments, grocery store runs, and endless laundry. And that’s not all: new moms need lots of support and ample time to recover.

But since Americans keep prioritizing EXTREME PRODUCTIVITY and individualism over everything else, most working parents don’t have time to get their lives in order. We’re expected to get back to the grind right away.

Don’t like it? Too bad. Stick that baby in a daycare, choke down a few painkillers, slap on a fake smile, and numb your way through the whole mess. You’ll see the kid on the weekends. It’s the American way!

Truth be told…the American way is fucked. This is what really happens when you go back to work so soon:

You’re a distracted, tired employee who’s running on fumes and whose mind is elsewhere.
You’re fighting with your partner because you’re overwhelmed trying to balance too much at once.
You’re missing precious time with your new child. At this early age they change every 20 minutes. You want to be there for that, and they need you to be there.

I know these things from experience. I had no parental leave when my daughter was born 7 years ago. I took a couple weeks of vacation and went back to work, leaving my wife alone with an especially feisty newborn. We slogged through it, but we suffered the fallout for a long time after that.

And I still had it relatively easy! At least I had some paid vacation time to use, and we could afford to have my wife stay home. Lower income families don’t have those options. If you’re earning hourly wages and living paycheck to paycheck, think you’ll skip getting paid when you suddenly have another person to care for?

These days, I’m so fortunate to work for a forward-thinking company with a generous parental leave policy. When my son was born in April, I was given 6 weeks of paid time off—a rare benefit for a father in the U.S.

Having that time allowed me to relax and focus entirely on my family. Being dad was my full-time job when it was needed most. I could do all the laundry, calm the crying, and help my wife get rest.

The family leave experience

I missed about a month of work, and everything kept on running without me. We put a couple of my projects on hold. It was fine.

My job paid me my usual salary, but even more than that, they gave me a priceless gift: dedicated time with my new son. That experience endeared me to the company more than just about anything else they could do. In return, I came back to work feeling enthusiastic instead of worn out and stressed.

Now, of course paid leave is wonderful for an employee, but how about for a business? Why should a company pay workers not to work? It’s already expensive to pay for health insurance and other employee benefits.

That’s a fair argument, but forcing zombified employees back to work doesn’t make their problems magically go away. It just causes extra stress and burnout. That results in higher turnover. And turnover is even more expensive! Research shows many businesses save money overall with a paid family leave policy due to reduced turnover rates.

Whether a national solution for parental leave in the U.S. involves a cultural shift, government action, private sector changes, or some combination of all three, I hope I’ve helped shine a little light on the truth.

If you’re an American worker, look for jobs that have supportive family policies. (They’re hard to find right now, but they do exist.)

It’s worth the effort. You won’t remember yet another month you spent at work, but you’ll never forget the beginning of your child’s life.

And if you care about this issue like I do, keep talking about it! Call your representatives. Talk to your boss. Let’s help change it for everyone and make this post obsolete.

Let’s stop trivializing design work

May 12, 2016

This week, Instagram updated their logo, and right on cue, the Internet exploded about it. This is not a post about that. Rather, this is a post about how we all critique design in public.

For example, this tweet got a lot of traction, especially from designy people:

Behind the scenes on the new Instagram logo pic.twitter.com/WPld3t0rJF
— Cody Sanfilippo (@codysanfilippo) May 11, 2016

And rightfully so…it’s a funny GIF. Anything with that thumbs up kid is gold!

There’s just one problem. Jokes like this spread the misconception that design is an easy and shallow aesthetic exercise. This seems to happen every time a major brand redesigns.

In case you’ve never made an app icon, here’s what it takes. (I just did this recently for my app Hello Weather.)

You need to:

Distill the overall concept and purpose of your app—and possibly your whole company—into a single visual symbol.
Design something that fits well with the platform’s guidelines about proportions and color use. This is harder when you support multiple platforms that have different guidelines.
Attempt to stand out a little, while not standing out too much, lest you come off as obnoxious relative to other app icons.
Find a color scheme that has good contrast and works in a bunch of different scenarios (on a black background, on a white background, on top of a bad photo of somebody’s weird poodle, etc.)

Preferably it should also be flexible enough to reduce to a simple black and white glyph as needed.

Did I mention it needs to scale up and down and be semi-legible from 16x16 to 512x512? An app icon is not just one icon. It’s all of these icons:

Icon size variations required for an iOS app

Oh by the way, you have just one tiny square in which to cram all those requirements.

So making an icon is trickier than it appears, and there are a lot of constraints to consider. A company as smart and design-minded as Instagram didn’t just crack open Illustrator and hack together an icon in 20 minutes — they probably designed and tested dozens of variations for weeks or months before choosing the final one.

Choosing is tough too. Let’s say you end up with 2 or 3 versions you like. There’s no way to know which one is right, but no matter what you pick, loads of people will tell you it’s wrong. An alarming number of people have the free time to tell you that they “don’t care for red” or any number of other equally inane comments.

It takes bravery and some pretty thick skin to launch stuff like this. Maybe it’s best to hide in a bunker for the week.

Here are some designers preparing for Internet feedback before launching a rebranding.

Overall, making an app icon is still a heck of a lot easier than landing a rocket on a boat in the ocean or the millions of things in life that are really truly difficult. But it’s not child’s play, either.

That’s why everyone has an app idea but only a small handful of people actually make apps: it’s hard to do, and even harder to do well. As designers who intend to be taken seriously (and paid well) for their efforts, we should acknowledge that and talk about it more often.

A good start is to change how you react to new design work in public. When people make big changes or launch new stuff, applaud them, support them, share positive comments or thoughtful critiques. Lead by example. That’s what you’d want them to do for you.

Why I love ugly, messy interfaces — and you probably do too

April 6, 2016

Illustration by Nate Otto

Beautiful. Fresh. Clean. Simple. Minimal. These words have been dominating design discourse for a while now. In case you’ve managed to miss them, check out this review of portfolio websites over on Creativebloq. The word beautiful is used 6 times, and simple 11 times. In one article.

Designers use these words to describe their values, goals, and results. They plaster their portfolios and resumés with them. Non-designers use them too. They’re everywhere.

If you’ve hitched a ride on this wagon, you might have a website that looks something like this:

compliments.dk

Lovely designs like this have become so commonplace that beautiful and clean are almost baseline constraints for new projects. It’s like every designer had the same Pinterest coffeeshop fever dream, and decided the whole world had to become lifestyle-chic.

And that makes sense, really! Everyone likes easily digestible things that look bright and stylish. Nobody wants ugly, messy stuff.

Or do they?

Here’s some ugly design that’s unbeatable.

Craigslist

Here’s some cluttered design that’s quite popular.

Adobe Photoshop CC

Here’s some complex design that 1.5 billion people use every month.

Facebook

So…wait. If beautiful, fresh, clean, and simple are so important, why hasn’t someone upended all of these products with something nicer? It’s not for a lack of trying. There are countless simpler, better-looking Craigslist and Photoshop competitors, for example.

The answer is that these products do an incredible job of solving their users’ problems, and their complex interfaces are a key reason for their success.

Let’s say your goal is to make a global peer-to-peer commerce network. That’s a big, complicated project to tackle.

You could attempt to reduce your solution down to a minimal version, cutting out features and reducing density in the name of beauty and simplicity. Here’s a Craigslist redesign concept like that. (Designers sure hate Craigslist, don’t they? Has any other site had more unsolicited redesigns?)

Craigslist redesign concept by Aurélien SALOMON.

Or, you might decide that you really can’t cut features, because it’s more important to nail every use case you care about. (Remember, you have to support a huge number of scenarios to reach table stakes for this project.) Now beauty and simplicity are instantly a much lower priority. Making something useful comes first.

For another example, think of Photoshop. How many graphic designers who idolize Swiss Style also use Photoshop every day? Probably most of them. Yet Photoshop’s UI is the antithesis of minimal — it has more nasty junk drawers than your parents’ unkempt basement. It doesn’t matter at all, because people don’t come to Photoshop for inspirational UI. They use it to get the job done.

In other words, sometimes this isn’t so great:

When this is what you really need:

Now, obviously I’m not suggesting you should go clutter up your design work, or make it look crappy on purpose. I’m also not suggesting that the examples above couldn’t be improved.

My point is: there is no single right way to do things. There’s no reason to assume that having a lot of links or text on a page, or a dense UI, or a sparse aesthetic is fundamentally bad — those might be fine choices for the problem at hand. Especially if it’s a big, hairy problem.

Products that solve big, hairy problems are life savers. I love using these products because they work so damn well. Sure they’re kind of a sprawling mess. That’s exactly why they work!

We needn’t all pray at the beautiful minimalist design altar. Design doesn’t have to be precious. Toss out your assumptions and build what works best.

This was originally posted on Signal vs. Noise. Adapted from a talk I gave at_ University of Illinois Webcon_.

How we made an iPhone app on the side

February 6, 2016

Getting a side project done—eventually.

Knowing the words is half the battle

February 3, 2016

One of my favorite career stories is this one from Michael Beirut:

I designed little magazines when I was in the third and fourth grades, and I made logos for my friends’ bands when I was in the seventh grade. I could do hand lettering, and if someone wanted an animal in the logo, I could do that; if someone needed a poster for the school play, I could do that, too.

All along, I had no idea that what I was doing was called graphic design. I lived in the middle of nowhere at a time when no one knew anything about something like graphic design.

By accident, I happened to find a book in my high school library…it was called Aim for a Job in Graphic Design/Art. I opened the book up, and it was like receiving an instruction manual for my future career: it was all right there. I was about 15 at the time, and I thought, “This is what I want to do.”

This bears repeating: one of the world’s preeminent graphic designers **didn’t know graphic design was a thing **— let alone a job you could get paid for — until high school.

He knew what the idea of graphic design was, and he even knew how to do it. But he didn’t know what to call it.

Perhaps the biggest obstacle to gaining skills in a given domain is knowing the right words. Being a beginner is intimidating because you don’t speak the same language as experts, who have often forgotten what it’s like to be a beginner.

If you’ve ever had to talk to a car mechanic, you know how it feels. In the immortal words of George Costanza:

Of course [car mechanics] are trying to screw you! They can make up anything, and nobody knows! “Why, you need a new Johnson Rod in here.” Ohh…a Johnson Rod…Yeah, well, better put one of those on!

Here’s another example. Millions of people use iPhones, but they don’t know the official names for all the interface widgets and the underlying stuff that makes them work. It doesn’t affect their ability to use an iPhone, because the iPhone is well-designed.

Customer:

I went to Twitter, then hit the thing that said “Notifications”, and a new screen came in, then I saw some messages, and it stopped working.

By contrast, an iOS developer knows the domain words, so they can be more precise:

Developer:

The customer opened the Twitter app, then selected the Notifications Tab in the Tab Bar. The Notifications Table View rendered for a moment but then the app crashed. The issue might be the Notifications View Controller or some malformed data in one of the notifications.

In product design, this is related to User Experience (UX). Part of a UX designer’s job is making sure a product’s internal language is either hidden away, or translated into common words that users can understand and interact with. If you don’t do this, you might end up with this kind of thing.

A customer support rep’s job is the opposite: they translate customer-speak into domain words so a specific problem can be resolved — especially in the case of a bug report that gets passed along to developers.

Here’s one last example. I’ve been an obsessive music fan for most of my life, but I’ve never formally studied it, so I don’t know the terminology. Check out this video of Jeremy Leaird-Koch building an electronic song from scratch on an OP-1. (Jump to 1:25 or so.) Be sure to watch the subtitles.

If you make it through the whole video, you’ll see a ton of expert language:

Sequencing
Swing
Delay
Kit
Wubbing
Phasing
Filters
Ambient poly lead
Modulation
Envelope sharpening
Arp (arpeggio)

I’ve put in 30+ years of music listening, and these phrases might as well be in a foreign tongue.

So it’s not enough to have exposure to the outer surface of a domain. If you want to level up your understanding, you have to be willing to feel ignorant for a while and study it in depth, until you find your sea legs and pick up a handful of those all-important words. There’s no magic to it. This willingness, and a lot of practice, is all that separates the experts from the beginners.

Once you’ve learned a bit of lingo, you’ll find that the words help you ask questions. The questions help you learn how things interact. When you know how things interact, you can start understanding the system as a whole. And pretty soon, you’re an expert too.

As experts who’ve put in the time, then, how can we make things more approachable for beginners? Wouldn’t it be nice if we could simply eliminate all jargon and special words? Then we’d have no problem, right?

Well, then we’d have a new problem: we’d have no way to talk to each other! Any sufficiently complex system needs names for its component parts— otherwise there’s no way to talk in detail about the system. So eliminating internal complexity isn’t always possible or even desirable. Still, there are a few things we can do to help.

Use plain words instead of fancy words.

For example, if you’re a programmer modeling a message sent by a client, call it ClientMessage instead of ExternalActorSubmissionContent.

Give abstractions familiar names, so they seem less foreign.

In Basecamp 3, we called group chats Campfires and direct messages Pings. They’re still abstractions that users have to learn, but at least they’re helpful names—a little descriptive and a little less intimidating.

Listen to how beginners talk about the problem, and inherit their language.

We did this recently by noticing our customers called Basecamp projects “Basecamps.” They’d say, “Oh, I made a Basecamp for that.” So we ran with it and called Basecamps Basecamps instead of Projects.

Don’t assume simple words are adequately clear.

Trying to be too simple or succinct is usually worse than being clear and verbose. This is why people are confused about what food is “healthy.” Even though healthy is a simple word, it’s an unclear way to define food.

If you’re in the privileged position of being an expert at something, don’t forget what it felt like to be a beginner. Let those battle scars inform how you communicate, and choose your words with intention. If you need a reminder of how it feels to be a newbie, just pick yourself up an OP-1 and let me know how that ambient poly lead turns out!

This was originally posted on Signal vs. Noise.

A rallying cry for the Weird Wild Web

September 25, 2015

This year, 2015, marked the 20th anniversary of the first time I stuck some HTML on a server and put it out for the world to see. (Sorry about that one, world.)

Twenty years! Twenty years is a long time to do anything, especially in tech. Given how fast things churn, it’s rather unbelievable that I’m still gainfully employed to write HTML for anything at all in 2015.

I’ve been reflecting on this recently, as the web’s future keeps sounding rather bleak. It seems that nary a week passes without someone predicting the end of the open web as we know it. Perhaps understandably so — at a glance, the web appears to be suffering a death by a thousand cuts.

Let’s recap a few of the most common arguments for why the web is totally screwed.

Corporations and governments are encroaching on the open web and trying to control it from all sides (bandwidth, access, content, etc.)
Social media sites are sucking up most of the traffic and attention. In the process, they’ve become stand-in replacements for the entire Internet (think AOL 2.0.) This has the side effect of turning smaller individual websites into irrelevant sideshows.
User-hostile advertising practices are degrading user experience on the web to an alarming extent.
Native apps provide a better and friendlier alternative to traditional websites-in-browsers. As native apps continue to mature, they’ll gradually eat the web with specialized UI for every situation — which means you’ll never need to access the web directly in a browser anymore. This will turn the web into a content delivery mechanism (i.e. HTTP requests) rather than an endpoint for users to interact with directly.
Web designers and developers are overusing slick copycat layouts, styling, and template tools. This makes web production easier and trendy looking, but at the expense of individuality and substance, leading us into a bleak dystopian future where web UI becomes the software equivalent of suburban tract housing.
Publishing platforms like Medium are piggybacking off independent writers’ content while offering relatively little differentiation or authorship credit in exchange. These platforms are gathering all the small-time folks under a few large umbrellas, thereby reaping most of the financial benefit while hammering more nails in the coffins of traditional independent blogs.

Alright, so wow. That all sounds pretty terrible, doesn’t it?

A lot of those things are true. The times are certainly changing, as they always do. We web folk should keep thinking seriously about this, lest we become the old crusty janitors left to turn out the lights.

But hold on. Forget about all those problems for a moment, foreboding as they may seem. Is there anything good happening now? How about:

Despite their repeated attempts, big corporations haven’t killed the open web — at least not yet!
Small mom and pop independents now have access to massive audiences that used to be impossible to come by. Whether your business is writing, art, or anything else, it’s easier than ever to get yourself out there and make a living or solve new interesting problems with the web. Kickstarter, Medium, and Etsy are incredible platforms for the little guy.
Web tech is as sophisticated, diverse, and powerful as it’s ever been. (Granted, we’re abusing it for bandwidth-munching ads and gratuitous effects — but that’s on us. We can stop. We should stop. Please, stop.)
Native apps haven’t eaten the web either. Native is fantastic and powerful and lovely, but you know who still has websites? Facebook. Instagram. Whatsapp. Medium. These are enormous services, some of which even launched as native-only and then added web versions later, because the web as a platform is still too important and universally applicable to ignore.
We — the small, independent weirdos — still have the power to meaningfully contribute to the web and change it for the better.

So where does that leave us?

First of all, let’s chill out for a minute. Maybe the naysayers are right and we’re all doomed, but the web is still alive and kicking right now.

Secondly, let’s reflect on our missteps and start walking back the most egregious abuses of slick tech and bad UX we’ve willingly let slide the past few years. Ad blocking on iOS is forcing the issue — but it’s rather sad that we let it be forced in the first place.

And finally…

Let’s make the web weird again!

Twenty years ago the web was super weird. No one had any clue what this thing was about or how it worked, so we were trying everything. Sites were badly organized, ugly, strange. Some were loosely organized communities. Some were just text. Even the best produced sites had the feeling of being held together by duct tape and straws.

Now to be clear, I’m not nostalgic for that time at all. Making websites sucked. Nothing worked well. The tech was painfully slow and limiting in every imaginable dimension. I don’t want to go back.

But the one thing the web had then, and which it has lost a lot since, was the sense of rampant experimentation. The feeling that it was fine not to have everything figured out or perfectly polished before letting people see it. That we were all in this bizarre human experiment together.

If we want the web to keep thriving, we have to start letting ourselves experiment (and fail) more. The web still has a low barrier to entry and the biggest possible audience. That’s an incredible thing.

So c’mon everybody. Let’s mess this place up again! Get weird. It’ll be better for it.

This was originally posted on Signal vs. Noise.

The special recipe for delight

June 3, 2015

Delight is a word interaction designers have been throwing around for the past couple of years. Some people think it’s an overblown buzzword, while others believe it’s a subject worthy of an entire conference.

One part of “designing delight” is about turning otherwise mundane tasks into funny or interesting moments. On the UI side, this might include adding thoughtful animations, cutesy or clever copywriting, and perhaps tossing in a few surprises on top.

These surface-level treatments help make a product seem more human and less computery, which is surely a good thing to do. But there’s another, deeper kind of delight. For this post I’ll call it DELIGHT. Here’s an example.

I recently moved my sizable photo library to Google Photos, for a variety of boring reasons: it syncs with Google Drive, storage space is generous, sharing albums is easy, it doesn’t mess with my existing file structure, and searching is miles ahead of competing services. Sure enough, it all works very well — currently besting Apple’s or Dropbox’s offerings.

I was already satisfied, and then Google Photos did something I didn’t expect. When I synced my tens of thousands of photos, the Google Photos “Assistant” bot worked behind the scenes to breathe new life into them, by automatically compiling them into animations, stories, and collages. The stories and collages were roughly what you’d expect a computer to achieve when laying out photos: a fine enough job, but not too mind-blowing. It was the animation idea that knocked my socks off.

As any parent of a young child (who just WON’T SIT STILL) can tell you, you often need to take 30 photos in a row to get one good one. So we do that a lot. This means our photo libraries are cluttered with countless batches of photos, most of which are basically blurry garbage. Who has the time to go through all of them to find that one perfect gem? Definitely not parents of young children!

Google’s engineers realized this, so they transformed all that garbage into something great.

Now that, right there, is DELIGHT.

Not only did this feature make amazing use of all those junky photos I haven’t looked at in years, it did so automatically. Google Photos just made my entire library much better without my intervention.

This feature has been around for a couple of years, but it doesn’t show off its true power until you backload your 10 years’ worth of stuff. And before now, backloading all your stuff sounded rather unappealing since the Photos feature was deeply intertwined with a big social network.

It took Google a long time to find the special recipe — that perfect combination of features, capabilities, and surprises — to get DELIGHT. To make it happen, they needed to mix cheap storage, tons of processing power, robust file syncing, plus a healthy dose of smart thinking and a willingness to decouple Photos from its social networking parent.

Now, DELIGHT isn’t really about the software itself. Seeing photos of your kid from 3 years ago in a brand new way is sentimental and emotional. It just so happens that the software helped make those emotions happen. I love my kid, not the software, but now I’m certainly more endeared to the software and the people who created it.

This is what product design is about. Finding the special recipe for DELIGHT. Making people badasses by giving them new superpowers they couldn’t have achieved on their own. Everything else along the way — the animations, the copywriting, the tech, etc. — is just supporting material for the main act.

This was originally posted on Signal vs. Noise.

Asking why

January 26, 2015

Last week I asked a question on Twitter: If you have a personal website, why do you have it?

Some people used their site as a hub that collects their online identities. Others liked to fiddle with web tech or writing. Several treated it as a showcase for their professional work, to possibly get a job. Everyone else, it seems, didn’t have a reason aside from a general feeling of obligation.

I think that last group indicates a sea change. In the early days of the web, your site was a big part of your identity. It was one of the best places to share information, prove your geek mettle, and make a little network of fellow weirdos. In 2015, we have a million other ways to do that, so a personal site feels left over from a bygone era — a tiny island adrift in a vast ocean of apps, status updates, and clickbait headlines.

And so, its purpose has become even more vague. People don’t know what a personal site is for anymore, so they go through the motions. They put the same things everyone else puts on there. A giant photo of a city. Something that says “Hi, I’m Dave.” Fancy scrolling effects. A bunch of social media icons. An unintelligible skills chart. A quickly neglected blog.

All these choices are based on assumptions. First, the assumption that you even need a website. Second, that a website looks a certain way and has this usual kind of stuff on it. And third, that some anonymous group of users will stumble upon it and be interested in it.

As an industry, we have this problem a lot. We do things because that’s how everyone else does things. We assume that what’s popular must be good, so we don’t ask questions...we just do it! Even if we’re not that into it. This is also why you see countless corporate websites that look exactly the same and automatically generated hipster logos. It’s much easier to assume an existing pattern works and reapply it than to dig in and find a deeper understanding of the real problem you’re trying to solve.

But shortcuts like this rarely lead anywhere new or interesting. Why replicate what hundreds or thousands of people already did? The best you can achieve is as good as everyone else. That makes you forgettable. There’s a simple solution: ask why you’re doing something, and don’t bother getting started until you have a clear answer. This applies to any situation, but in this particular example...

Why should this website exist?

That question leads to more specific questions...

What am I trying to get out of this? What’s unique about my story? Do I have anything to say? Why would someone look at this? Why do I want them to look at it? What do those visitors really need to know? What should they do next?

When you work outwards from why, you unlock all sorts of revelations that aren’t about obligatory features or popular trends. You might find that those scrolling effects and skills charts have nothing to do with your story and the outcome you want. Maybe you’ll uncover a parade of new ideas dying to see the light of day. Or you’ll decide your site is just for your own experimentation, and that’s OK too.

If you find no strong reasons for a project to exist, all the better! Kick it to the curb and free yourself to spend time on something else.

This was originally posted on Signal vs. Noise.

Strategies for getting feedback (and not hating it)

January 20, 2015

Recently my team has been working on core product improvements. We planned to move quickly on a range of projects, and we wanted to make sure everyone at the company stayed in the loop. Plus, our company is full of smart folks who know the product inside and out, and we were hoping to use that hive mind to our advantage.

That’s easy when you have 5 or 10 people, but it’s challenging with 45. We had to share a lot of info and avoid pestering everyone in the process, so we began experimenting with a few new ways of working. Some of ‘em worked, others...kind of worked. Here are a handful of the strategies we tried the hard way.

Make screencasts for easier reviews.

No matter how many times you’ve done it, asking people for feedback is a harrowing ordeal. They’re busy working on something else, and you’re requesting their precious time and attention.

We wondered: what’s the most effortless way to communicate what we’re working on? Long written messages or storyboards take a lot of time to wade through. So instead of that, we started making 3-5 minute screencast demo videos for each project-in-progress. We share these videos with everyone at the company and ask them to comment. They’re friendly and easy to watch.

In each demo, we talk about the motivation behind the project and what we’re trying to accomplish. We explain how our solution addresses those things. We also mention weak spots or details we’re not sure about.

These videos helped quell broad questions like “why are we even doing this?” because they demonstrate that we’ve thought through the big picture stuff. As a result, the criticism we receive is more specific and actionable. Sidenote: if you do this, you’ll have to get comfortable recording screencasts. After about 5 of them, you get the hang of it. The first step is accepting that yes, your voice is weird, and your face is kind of weird too, and wow, you’re not good at this at all, are you?

Seek out people who have different perspectives.

Getting the truth isn’t always as easy as mass-emailing people. You might actually have to talk to them. Sorry, fellow introverts!

We’ve made a concerted effort to chat with people outside our immediate development team, like our customer support people, data analyst, QA folks, and anyone else in the company who might look at the problem from a different angle. Sometimes they don’t speak up on their own, but if you reach out personally, they’ll almost certainly mention things you never considered.

Decode vague comments.

How many times have you heard (or said) stuff like this?

"This one looks more readable." "I like how this one is clean and simple." "This version makes your eyes jump to the important part of the page." "This seems like it’s the most usable." "This solution might be too noisy."

This feedback isn’t necessarily bad, it’s just incomplete. Words like clean, usable, and noisy don’t have much meaning. They roughly suggest something about hierarchy, contrast, and spacing.

When we get feedback like that, we dig deeper and ask for clarification. If something looks more readable, why? What about the design is better? More whitespace? Typeface pairings?

Once you unravel the real issues, you’ll know which direction to go. You’ll also get better at offering suggestions to others. Instead of saying, “hey this design looks bad and weird,” you’ll say, “this doesn’t fit in well with our usual styling.” Details like that give your colleague a hint about what they need to improve.

Emotionally separate yourself from your work during critiques.

If you’re working on a project you care about, you’re invested. Sharing your work puts your ass on the line, and hearing a negative reaction will sting. (Admittedly, it’s even harder in front of the whole company. Your ass is on all the lines.)

But the only way to make something great is to recognize that it might not be great yet. Your goal is to find the best solution, not to measure your personal self-worth by it.

Furthermore, most people are reluctant to tell you what they really think. Got negative feedback? Cool! You just succeeded at finding the truth. That’s a win in itself.

When it’s time to share and evaluate what you’ve done, try to put your emotions and sweat equity aside. If you can manage this, you’ll be able to debate the ideas logically instead of emotionally.

When nobody responds, you probably haven’t nailed it.

We noticed that people rally around an obviously good or bad solution. If a solution is strong, you’ll hear about a few minor nitpicks, usually interspersed with an excessive quantity of happy emojis. If it’s clearly bad, a few honest folks will call it out (with not so many emojis.)

When the team is indecisive, or worse—silent—there might be bigger underlying issues at stake. The best way to move forward is to get the whole team together and air it out. Get on the phone, or Skype, or have a meeting and chat in person.

We did this with a project that wasn’t going so well. We were creatively stuck, but we’d been trying to work through it individually. When we reconvened as a group, everyone had a chance to voice their concerns and agree on what to do next.

Make the call.

What happens when everyone disagrees? You might have multiple viable ways to proceed and no definitive answer on any of them.

Now it’s up to you to weigh everything you heard. How much time do you have left to make changes? Which solution do you feel strongly about? Does someone else feel strongly when you don’t? Is there a compromise version, or another option you haven’t considered yet?

The answers here are always different, but one thing remains the same: it’s up to you. It’s tempting to pawn off these decisions to other people, or wait for a consensus to appear, but it’s better to choose a direction than to keep spinning your wheels trying to please the group. Making the call has the side effect of drawing out people who were on the fence — if it’s the wrong call for some reason, they’ll speak up before it’s too late!

Don’t be embarrassed when things don’t work out.

Not every project is an immediate success...or even an eventual success. Out of our last 10 projects, 2 didn’t go smoothly. The first one shipped after we took a break and regrouped. We shelved the second one entirely, because we tried numerous approaches and there was no clear path forward.

Admitting defeat doesn’t feel great, but it’s far better than trudging ahead with a design that simply isn’t working. Who wants to ship and support something like that?

Return the favor.

Try offering thoughtful critiques of others’ work. Be kind, honest, and specific. It’s surprisingly difficult to do!

If you’ve been in the game for a while, coach and mentor others. Help them improve and share the feedback love. Teach them to screencast so they’ll get used to their weird voices and faces too (eventually.)

This was originally posted on Signal vs. Noise.

Writing-first design

November 21, 2014

A quick way to measure a designer’s maturity is to watch what they do at the beginning of a project. Inexperienced designers are often smitten by the allure of new tools and quick results, so they’ll jump in to Sketch and start messing with layouts and style explorations. Seasoned designers know this can be distracting, so they might start by doing research or drawing in a paper sketchbook instead.

Sketching is great, but before I start sketching, I start writing. Writing first has lots of advantages, regardless of the project you’re working on. Here are a few examples.

Example 1: You’re making a simple website, and your client doesn’t have any copy yet.

Great! Here’s an opportunity to write it. Skip the lorem ipsum and start telling your client’s story. What’s special about this client? What problems are they trying to solve by having this website? How can you explain those ideas to people who visit the site? And why should the site’s visitors care?

Answering these questions requires you to gain understanding. You can’t write anything without knowing your subject. You’ll be forced to learn a lot about the client’s business, their history, and their audience. Having this information will clarify your vision for the overall project.

Example 2: You’re making a website, and the client gave you copy to start with.

Great! Don’t design anything yet. Put on your editor’s hat and think critically. Is the text arranged correctly? Does it have the right tone of voice? Is it too long or too short? Is it suitable for the web? Can you chop it up into separate pages and keep it coherent? What’s still missing?

Chances are, this handed-over writing might be lousy. Be honest and propose copy changes before you get much deeper into the design. Don’t be afraid to do a rewrite — treat writing as part of the design, not just an element on the page.

Example 3: You’re making an app or interface elements.

In that case, you’re likely designing affordances — communicating actions the user can take. These might take the form of explanatory copy, prompts, buttons, labels, error messages, etc.

Great! Hop into a text editor. Write out as many variations as you can. It’s easy to mock basic UI in text, like this:

Are you sure you want to delete that file? [ Yes, I’m sure ] [ Never mind ]

Deleting this file will remove it permanently. Are you sure? [ Yes, delete it ] [ No, cancel ]

And don’t be afraid to have a little fun with it:

That file will disappear completely and never be found. Carry on? [ Indeed, ashes to ashes and so forth ] [ No, I can’t let go ]

Example 4: You’re making a graphics-heavy poster that has almost no writing at all.

Great! Write down what you think you’re trying to accomplish. Spend 5 or 10 minutes on it. The notes are entirely to help you clear your head and figure out what to do.

Putting writing first improves your chances of success in the final product. It’s good practice, and it makes the rest of your job easier.

Now, what does the overall creative process look like? I’ve found it works well like this:

Spend time writing until you’re happy with the first draft.
Sketch visual ideas on paper.
Open your software tool of choice and explore aesthetics: colors, type, imagery, and style.
Put it all together and try different layouts and arrangements.
Continue editing once you see everything in context.

Obviously that exact order is not always right for every project. There’s no right way to do things! But following this general process helps guarantee you’re staying on the right path.

This was originally posted on Signal vs. Noise.

The power of free design: why you should do pro-bono work (sometimes)

August 26, 2014

A few months ago, my uncle Tim started a project to restore a small theater in downtown Antioch, Illinois. The century-old theater had closed due to general disrepair and outdated tech. It needed an extensive revamp, and it was going to be costly.

Tim's a real estate developer, and he was putting up his own money to get this project off the ground. But he needed help. He wanted to do a Kickstarter project and a fundraising campaign to raise $100,000 for the renovation.

He asked me if I had any recommendations for someone to make a website:

I need somebody good, fast, cheap and available. That's only 1/2 a joke.

The only person I knew who fit that impossible criteria was me! I believed in the spirit of the project and thought it was worth my side project time. So I offered to help (for free.)

He had some rough marketing materials drafted, but it was clear we needed something more cohesive. I asked him to tell me the story of the theater, so I could get a sense of its past and future. From there, we moved on to visual design. I explored some type and color treatments and we chose a logo.

Logo sketches. We had the name spelled wrong.

Then we designed several print materials to get the word out locally, including brochures, posters, and an enormous 200-square-foot banner to hang on the front of the theater:

One giant banner.

Finally, I launched the website, while Tim's team got the Kickstarter campaign started and planned promotional events.

Throughout the whole project, we spent extra attention on copywriting. We carefully explained the theater's rich history and its ongoing value for the downtown. Bottom line, if anyone was going to give us money, they had to understand why it was worth it.

All together, I spent about 3 weeks of my occasional spare time on the project, and we ended up with a strong marketing effort, with a unified look and a consistent message. If you were anywhere near downtown Antioch, you couldn't miss that SAVE THE ANTIOCH THEATRE logo on posters in every shop window.

But even with all that promotion, we weren't so confident this would succeed. Will people care about a neglected old movie theater? Can we really raise $65k on Kickstarter for a small suburban town? For a while, the campaign stalled out around $25k and it seemed like we were done.

Not so. In fact, the campaign took off like crazy, and we ended up raising nearly $20,000 more than the original goal—enough to hit a stretch goal and upgrade the projection tech to 3D.

So, marketing done, money raised, theater saved! End of story, right? Not quite. Turns out that the campaign built a wave of energy and kicked off a broader movement toward improving the entire downtown:

I am not exaggerating this, but the messaging has inspired key business people to engage in the overall downtown revitalization effort, and has instilled a belief that things can get done. They see that residents will respond to quality.

This is what design can do—it can inspire people and change things for the better. It's easy to forget about that when you're doing client work, or routine production work, or whatever your day-job specialty happens to be.

Furthermore, pro-bono work gives you a chance to stretch your legs and try stuff you've never done, which can improve your day job work too. With this project, I took time to learn Sketch and used Basecamp with folks who were new to the product. I discovered some interesting challenges with onboarding, and used features I rarely use in my regular work. These lessons will help me improve Basecamp.

If you have the means and the time, take on some free work* once in a while. Help out a cause you feel strongly about. When money's not at play, you'll be motivated by an entirely different set of factors, and you might be surprised by the results.

*Jessica's chart holds true: be careful to set clear limits and scope on the project, so you don't get abused and everyone knows what to expect.

It’s OK not to use tools

May 21, 2014

Recently I did a little side project to improve the website for a non-profit animal shelter in our town. The existing site was an outdated Microsoft FrontPage menagerie, so basically anything I did would be a big improvement.

I spent around 20 minutes creating a simple design in HTML, and then several hours editing, rewriting, and refining the copy. In the end, I reduced a scattershot 25-page website down to about 8 focused pages written in a friendly tone.

My next instinct was to apply our great modern web toolset to the site. Let’s add a static site generator or a CMS! Let’s add Sass and a grid system! Let’s do more fashionable things!

Then I started looking at those tools critically. A static site generator usually requires knowing Markdown and esoteric commands and configuration. A typical CMS will need setup, logins, security patches, templates, and maintenance. Even hosted CMSes have a lot of cognitive overhead, and the content is trapped away inside someone else’s system.

These are tools made by geeks, for geeks. Why do we need a CMS for an 8-page site? And for that matter, why even bother with Sass? Regular old CSS can do the job just fine.

Who knows who will take over the site in the future. I’ll hang with it for a while, but someday someone else might have to work on it. It would surely be easier to do that with 8 simple, straightforward HTML files than with some custom WordPress installation that’s several versions out of date. So what if I have to repeat the navigation markup 8 separate times? It’s not that hard. We used to do it for much larger sites!

Today, a basic HTML/CSS site seems almost passé. But why? Is it because our new tools are so significantly better, or because we’ve gone overboard complicating simple things?

As builders, we like tools and tech because they’re interesting and new, and we enjoy mastering them. But when you think about the people we’re building for, the reality is usually the opposite. They need simple designs, clear writing, less tech, and fewer abstractions. They want to get stray animals adopted, not fuss around with website stuff.

Remember when the web was damn simple? It still can be. It’s up to us to make it that way.

This was originally posted on Signal vs. Noise.

On writing interfaces well

September 24, 2013

Interface designers like to talk shop about visual styling: colors, icons, type, gradients, shadows, spacing. If it can be tweaked in Photoshop, there’s probably a lengthy Twitter debate about it.

Aesthetics are debatable, but writing is essential. Peel away the layers of styling and you’ll be left with words. Writing is the meat of a design, and it’s one of the hardest things to get right.

So why don’t designers talk about writing more often? I think there are three reasons:

It’s not sexy. 15 edits of a single sentence don’t make for a flashy portfolio piece (although I’d love to see more portfolios like that.)
We’re all pretty bad at it. Writing is difficult, and most of us probably weren’t trained to do it well.
We think people don’t read. Jakob Nielsen’s research showed that people don’t read on the web, and on average, they’ll read only 20% of the words on a page.

As a result, designers undervalue text. We cut copywriting back to the bare minimum. Sometimes we exclude important details to keep things short. We overload interfaces with obscure icons, invisible gestures, and no explanatory text at all. Instead of “writing” or “copy” we even call it something generic: “content.” The measly text we have left is often a low quality afterthought.

Who cares, right? People don’t read anyway. Well, maybe they don’t read because they know what they want, and this junky writing is a waste of their time. How can we improve?

Write better words, not fewer words.

Writing for interfaces isn’t just about brevity. Brevity is a luxury that you can occasionally get away with. It may take quite a few words to explain what’s happening, and that’s fine — a paragraph of clear instructions is better than a vague sentence. (Though a clear sentence is better than both of those.)

Here’s an example. I worked on the recurring events feature for the Basecamp calendar, so you can schedule an event that happens more than once. When you edit a recurring event, Basecamp asks what you intended to do. Did you want to change just that one event? Or subsequent events too? Maybe you didn’t know this event repeated, so you might be surprised at the question.

At first, I wrote a concise, robotic version of this dialog:

You're moving a repeating event. Which events to do you want to update?

Only this event

All events in the series

Never mind

Good enough? Nope. What’s a “series”? What does any of this mean? Exactly what’s going to change? There’s no way to know. This text makes too many assumptions.

After a round of feedback, I tried a second version:

You're moving an event that repeats. Do you want to move all future versions?

Move all future versions.

Move this one only.

Never mind, don't move anything.

This is a little better. Now we know that we’re only concerned with future versions. But this copy still feels repetitive and mechanical. After a bit more feedback, we ended here:

You're moving a repeating event. Do you want to move all future versions of this event too?

Yes, move all future versions.

No, just move this one and keep the others where they were.

Never mind, don't move anything.

We added a lot of words! But now the choices are clear, and the tone of this text feels more natural and friendly.

Write for your friend.

Most of us learned to write in the Official Style, in which your message is mostly obfuscated by nouns, buzzwords, and other garbage. It’s the writing you’d use to meet the 1,000-words length requirement on a term paper.

That’s the opposite of how you should write copy for your website or app (or anything, really.) Instead, write like you’re talking to a friend who needs help. Be casual, positive, and encouraging. If you wouldn’t naturally say it out loud, it’s not right. Keep working until it feels natural. Edit relentlessly.

Good writing is good editing. Remember that people will only read your words when they’re motivated, so make it worth their while. Say everything that needs to be said, but no more. Set a high standard for yourself — would you want to take the time to read this? Edit, edit, and edit again until you nail it.

Quality writing is hard work that takes time, but it’s worth it. Accumulated across your entire website or app, consistently good writing will help reduce your users’ confusion, and your customer support burden to boot.

Forget about Jakob’s 20% rule. Make your writing 100% worth reading, and people will read it.

This was originally posted on Signal vs. Noise.

A message from some far off star

August 5, 2013

My grandmother died 17 years ago, due to complications after heart surgery. I was 16 then.

A few days ago, my mom gave me a letter that grandma wrote to me before her surgery. I didn't know this letter existed until now. Receiving it almost 2 decades later, as a grown adult with his own family, somehow made it even sweeter and more impactful — a shot directly to the heart. It's the best letter I've ever received, and some of the best advice. Though it's a private note, I wanted to share her wisdom with you too.

Jonas -

That last letter you wrote to me was so wonderful. But then, you have always been wonderful and dear to me. I know that you know this -

I wish for all 3 of you happy years ahead, and compassion and caring and faith in others and yourself. Love and be a caring and dear son as you have always been. For your closest family will be the strongest and most loving part of your life, including your wife and kids to come. Peers come and then go. Though it seems they will always hang around, somehow this isn't the case, and within a fairly short time they are scattered here and there. So it is your family who will always be in your corner.

And so will I, from some far off star!

I love you

Love - Gramma

Tips for quick and flexible design prototyping

July 18, 2013

This article was originally published at netmagazine.com. With their site transitioning to Creative Bloq, I'm republishing here for posterity.

For the past several months at 37signals, I've been working on a new app called Know Your Company. At the beginning of the project, we had a lot of ideas, but we weren't sure if they would gel into a cohesive product or not.

To find out, we built a functional prototype. During this phase, I stayed mindful of how I approach design problems. I wanted to forget my past tricks, build things better and faster, and try crazy stuff outside of our comfort zone. Here are a few tips I picked up along the way.

Start with the essence

When you're first starting out, the sky's the limit, which is both exhilarating and overwhelming. Narrow down by identifying the core of your idea. What's the one thing that's so important, the project couldn't exist without it? That's what you should work on first. Start exploring and see if it even has legs. If not, regroup and start anew.

Focus on what it does, not how it looks

Conceiving ideas is hard and fiddling is easy, so you might lose your mojo by working on unimportant details too soon. Be disciplined, focus on capability and avoid distractions that slow down your progress.

We fell into this trap. We accumulated too much styling in an early version, and started wasting time debating it. Realizing our folly, we switched the entire UI to plain black and white to ensure we were working on the real problems.

Hang loose

Once you have distractions under control, play it fast and loose. Try your wildest ideas first. You can always fall back to something more conservative if they don't work out.

We always like to experiment with weird elements — interesting shapes, animations, colors, or layouts. Forget what's been done before and do something different. Look for real world inspiration.

Follow interesting paths

Ideas build on themselves. One idea leads to another, and suddenly you have a diverse pool of things to try.

Often these evolved ideas are stronger than your first ones, so don't be afraid to change course for a few days. You might end up with a final set of features that's entirely different than your original vision.

Throw it out

Many early explorations are junk. That's healthy. At one point we trashed thousands of lines of code. Don't get attached to what you already built - be critical, let it prove its worth, and relentlessly cut anything that isn't working.

Do Repeat Yourself

When you're working on a production app, optimization and the Don't Repeat Yourself principle are important. But for a prototype, some duplication can be beneficial.

Let's say we're working on two similar features: messages and notes. Those interfaces and behaviors are similar, so you might be tempted to optimize right away and make them share CSS styles, markup, JavaScript, etc.

But maybe next week we'll decide that messages should look or work much differently than notes. Or we might axe the messages feature altogether. Then all that optimization work was pointless.

Keep things decoupled until you're certain they're sticking around.

Fake it

A prototype should be as real as you can make it, but don't go nuts. If something is too hard to build, stub in examples and get things as close to real as possible. (My early measure of "too hard" was anything that took more than an hour or two to figure out.)

As an example, at first we didn't build authentication into the prototype, we just pretended there was a logged-in user.

Keep the momentum going and review often

Working on new stuff is fun, but there's also no obvious deadline for when you're done. So keep hustling and cover as much ground as you can. If you hit a lull, get out of it quickly by reconvening and deciding what's next.

I also stayed motivated by watching my daily commits. I like to see a lot of progress every day, and Github's profile page is great inspiration for keeping the streak going.

Mop the floor when you have free time

When you're moving fast, trying ideas, cutting features, and stubbing in examples, things can get messy in a hurry. Take occasional chances to weed the garden.

We like to keep a "Chowder" list in Basecamp for minor problems that need attention. It's the perfect list to tackle when your creative juices are tapped out, or if you're waiting for someone else to finish some work before you can move on.

Know when to stop

At some point, the prototype needs to get real. This time we waited a little too long and had polished too much before calling in a programmer. This made it overwhelming for him to jump in cold. A good lesson learned – prove the concepts as fast as you can. If you're confident the idea is strong, then get to work building with a real production crew.

So that's what I've learned this time around, but the creative process remains a mysterious beast. What tips do you have for taming it?

What my daughter taught me about worrying

May 2, 2013

My daughter is an intense person. She's curious and imaginative, introverted but outwardly compassionate, wise but silly, and deeply emotional. In her four short years, she has taught me more about my own life and character than I will likely ever teach her about hers.

But all those wonderful traits don't come without a cost. Her sensitivity leads to frequent bouts of worrying. We don't live a particularly stressful or troubling life — as careful guardians of her well-being, we're purposeful about limiting her exposure to grown up problems.

So her worries are largely focused on simple matters. When she was younger and lost a toy, she jumped to absurd conclusions: "Is it under the house? Under the fridge? Is it in a tiny corner? In a vent? In the wall?" She worries that her mother has left the house without her knowing. She worries that her betta fish has died when it's not moving. She worries that the stuffed animal she wants will be sold out. She cares about everything, even the flaked-off bits of polish from her painted fingernails, so she must carefully save them from an uncertain fate. And the list goes on and on.

A worrysome text message.

These issues aren't uncommon. She's learning to manage her feelings and her level of control over her environment. These are healthy steps that will help her cope with bigger problems later.

But helping her through this phase has made me reconsider what we think of as "grown up problems," and how we handle those problems. Trivial worries don't go away with age, they just multiply. Adults worry about a tremendous number of things, many of them far more insignificant than the lost toy that's theoretically stuck under the refrigerator.

Think of all the things, big and small, that probably concerned you today:

Which shirt should I wear? Do I look presentable enough?
Global warming is going to be awful.
Uh oh, I'm running late.
The lawn needs mowing.
Hey, I have new Twitter followers! I'd better think of a smart tweet.
What's going to happen 15 years from now?
Am I getting enough done? What do others think of my work?

…and THAT list goes on and on, and on…

How do we deal with these worries? Some, we internalize. Others, we act on. And some, we need help solving. But regardless of our ability to manage them, why do we allow this crap to consume and distract us every day?

As pompous adults, we assume that our age and experience has granted us a righteous view of the true world. We're eager to instruct our kids to get over their childish nonsense and join our reality. And then we teach them how to be agitated about unkempt lawns, baseball scores, physical appearances, and cell phones.

This is bad. Child worldviews are open ended and full of ideas and wonder. Adult worldviews are cynical and full of pointless bullshit.

For now, I'm going to be critical about what worries me and occupies my mental attention. I'm sure the kid will teach me a thing or two about what really matters and how I should feel about it. In the meantime, I'll be right there with her in child world, for as long as she'll allow me to visit.

Learning programming made me a better designer

February 22, 2013

At 37signals, our designers write code. Not just HTML and CSS — Ruby and JavaScript too. We can all get reasonably far implementing an idea before calling in a programmer for help.

I was lucky to get a crash course in Rails when production for the new Basecamp was kicking into high gear. But even after a year in the trenches, I wasn’t confident I was Doing It Right™. So last fall I took the Rails for Designers class at The Starter League. Obviously, the class helped me get better at programming. I wasn’t expecting it to transform my design process — yet that’s exactly what happened.

Before you can walk, you have to stand on your own feet.

An interface isn’t just a series of static screens pasted together. It’s a flow, with inputs and outputs. You can’t truly evaluate an interface until you can use it, and you can’t use it until you build it. Anything less than the real thing is a fuzzy approximation.

It’s fine to bring in a programmer when you’re confident that your idea is worth building, but what if you’re not so sure? Now you’ve used someone else’s time and mental energy to make something that might hit the dumpster. That stinks.

This hit home recently when we started working on a new app. Before, we’d make a static mockup or build a few working pieces and then call in a programmer assist. This time, we’ve been able to stay in the prototype phase much longer – almost 2 months – without having to use up a programmer’s time to test concepts and explore ideas.

You don’t have to be a code master. I am most definitely not. If you can just make things functional, that’s enough to evaluate and a huge head start for a real programmer to make it great.

An ode to writing at night

February 20, 2013

Morning is a dreadful sight
My groggy brain be stale
Afternoon could be alright
But still to no avail

I try to write at dinner time
Cacophony abounds
After dinner no such luck
The child's making sounds

Evening time is plenty fine
I'm feeling so much fitter
Regretfully I realize
I wasted time on Twitter

At last I've time to grab a pen
And sort out all my thoughts
Too bad it's after midnight now
The words are mostly blots.

Building a website with Symphony

July 10, 2011

Between 2010 and 2011 I wrote a series of posts about building a data-driven website using Symphony. Those posts have been offline for quite a while, but people still ask me for them all the time.

So, I cobbled them together into a single PDF for reference. Download below, and enjoy!

Building a site with Symphony (6MB PDF)

This Ephemeral Year

February 2, 2011

In 2010, I rebuilt my website. As is my way, I overloaded the project with too many technology changes, forcing me to learn tons of new stuff before I could do any real work. I also fell into the worst client trap of being perpetually unsatisfied with any design I produced. Nevertheless, I trudged on, and finally decided it was decent enough to launch in March.

One of the new features was the Ephemera section, which was rushed out the door at the last minute, but turned out to be the best addition to the site. The idea was to start tracking little memorable bits of my life — items that would otherwise be lost in time. I have a terrible memory, and I'm finding that my once-reliable Internet footprints are getting more and more fragmented across many different services. Back in the good old days, you could just read your email archives and remember everything that happened.

The Ephemera page does two things. First, it provides simple statistics about my various web activities. Second, it displays a record of my actual, physical life, which means that I'm required keep a minimal daily log of what happens. I had zero confidence that I could maintain even the most rudimentary task on a daily basis, so I kept it dead simple: a one-line text annotation, and a quantitative (0-10) ranking of the day in four categories: Mood, Workload, Sunlight, and Sleep.

So, what did I learn?

Merely logging into a website, choosing four numbers, and writing a one-line sentence every day is incredibly hard to keep up. Feltron has the right idea by "outsourcing" the data collection.
If you miss a day, or a week, you won't remember what the hell happened yesterday — let alone last Tuesday.
Life is filled with countless meaningless interactions and uninteresting chores. Some days memorable things happen, and other days you eat pancakes and clean up cat barf.
It's hard to be quantitative about your life. As an example, should my daily Sleep entry be an exact representation of the number of hours I slept, or should it be qualitative relative to how tired I really feel? It's a judgment call.
Trends confirm that moderation is good. Big surprise, mood plummets as workload nears maximum!

How it works

I've been dreaming about doing native/live data visualization on the web for years. The technology is finally coming around; there are numerous libraries and tools available that do in-browser charting, using either SVG or the <canvas> element to render the charts. I tried almost all of these and settled on Highcharts for this project, as it was the fastest way to get some decent output. I combined that with a healthy dose of CSS effects, and there you have it!

View the project here.

Glitch art

August 10, 2009

In 2006, I wrote a short essay about Glitch Art for Ninth Letter. I'm posting it here for posterity and reference, since a few places around the web still refer to it (including Wikipedia.)

Glitch Art (2.0MB PDF)

Collecting life

June 21, 2009

My grandfather passed away on New Year's Eve, 2004. He was a complex and conflicted guy. At times he could be inexcusably harsh, but he also had a sly and silly sense of humor. This Jekyll/Hyde situation left one guessing as to which grandpa would show up on a given day, but I rooted for the sweet, funny family man, and tried to dismiss the cranky curmudgeon when I could.

In his later years, he became increasingly immobile and dealt with chronic pain. He was a great outdoorsman, a navy mechanic, and craftsman in his youth, but years of hard work and the resulting physical damage caught up with him. Still, he kept up with several hobbies even as his body failed.

Joe Downey on a tiny bike on a Navy ship.

When I was a kid, my grandpa turned me on to coin collecting. It's definitely a "young boy and his grandpa" sort of activity and I'll always identify it that way. These days I have little time to devote to squinting over dimes and looking for mint marks, but I still appreciate the storytelling and historical aspects of collecting. When I see an old coin, I like to imagine who held it in their hand before me, and what was happening the day that chunk of metal was violently smashed into something valuable.

Maybe because he was bored and stuck in the house, or maybe because he simply liked it a lot, Grandpa collected coins until his last day at home. He had established a fairly substantial eBay habit to fill gaps in his collections, but his main late period interest was the state quarter releases. Most curiously (and resourcefully), he chose to organize the quarters in prescription pill bottles, each carefully labeled with the state's name and mint. For the finishing touch, he engineered custom wooden shelving to hold each one of these pill bottles, with little circular holes for each one.

Quarters in pill bottles.

I couldn't help but love this. For starters, it's telling that he had so many pill bottles at his disposal, though I hope they weren't all from his own prescriptions (maybe he made friends with a pharmacist!) He lovingly and obsessively sorted these coins, but for what purpose other than his own amusement isn't clear — he may have intended to share the collection with the grandkids someday.

Most bittersweet is that the quantity of coins per state decreases markedly over time. The early pill bottles are overflowing, but later states are represented by only one or two coins; the collection whimpers to an end abruptly at state 35 (West Virginia), which was the last quarter released before his death. He had the full intention of completing this collection, as I also have 15 states' worth of empty, pre-labeled pill bottles that never met a quarter.

These bottles have been sitting in a box in my basement since mid-2005. Mainly, I've been too busy to do anything with them, but I've also been in a quandary about what to do. I was initially planning to complete the collection, but I decided against interfering with such a vivid snapshot in time.

We could also just cash them in. (Individually, they have high circulation rates, and aren't in a physical condition to be worth much above their face value, even many decades from now.) My grandpa had a more valuable collection of older coins — which we are also storing — and our storage space is at a premium!

But cashing them in would neglect the object quality of the overall collection. All together, this is his last work. I envision him assembling the bottles, labeling them, analyzing each quarter and placing it in its right spot. I suspect that like any good journey, the process of collection was more entertaining than the end result. Yet the end result (and my imagining of Grandpa's process) is all I've got left.

The question I can't answer is: do we honor our relatives by keeping up the material things that meant something to them? Or do we simply acknowledge their contextual worth and move along? In a life busy maintaining our own odds and ends, what place do these objects have? If their value consists primarily of nostalgia or memory, then maybe the trash heap (or in this case, the bank) is where they belong. I just wonder if discarding the objects will inadvertently put the memories in the trash too.

For now at least, I still have the bottles. In a box. In my basement.