Dictation With a Twist

Want to dictate in one language but write in another?

Lispr is an advanced dictation app that just dropped this insane feature. (I was one of the first people to sign up for it.) Note that right now the only three real-time translation options are English, Spanish, and French. I'd be shocked if more don't arrive soon.

An Invitation to the Hot New AI App

I wrote recently about the Siri AI that Apple should have launched. If you'd like in on Instinct, click here. (First come, first served.)

DIY Software

Want to roll your own version of [insert name of app or program]? Go nuts with Reverse Engineer Anything that's currently terrifying Adobe's senior management. Every exec at every software vendor ought to be paying attention to this powerful GitHub.

Access Your Mac Anywhere

Want to dial in to your Mac via your iPhone, iPad, or another Mac? Go nuts with Screens 5 (paid) or go the open-source route with Sill. I tried the latter. It worked like a charm.

Feed Me

Finally, looking to score a deal on food while preventing it to go to waste? Check out the Too Good to Go app.

A Rant

Last week Apple dropped the HomePod mini v2. Better chip? Check. More expensive than its 2022 predecessor? Check.

A complete product? Crickets.

Evidently, it's acceptable these days to ship a product without a key feature: Siri AI.

Would I like a new home speaker–and a smart one, to boot? Sure, but I'll pass on Apple's latest product for now.

Remembering RJ Mitte

On a sad note, the actor best known for Breaking Bad died far too young last week at 34. Damn shame.

See you next week.

Feedback

Any tips for me?

Yesterday Notion announced a modified pricing scheme. Simple it is not. AI credits now fall into three buckets.

The company's post here explains the changes but lacks a proper visual. I fired up Claude and decided to create one. I know that my clients and I will benefit. Maybe you will as well.

From the post:

Simon Says

We'll see if Notion's claim ultimately holds true.

All prescriptive nonfiction titles should contain clear, professional visuals. The right charts, graphs, and tables don't just give readers' eyes a break from endless text blocks. They also prove that the authors have done their research. Think of them as credibility steroids.

My 2022 release Project Management in the Hybrid Workplace is no exception to this rule. One of many its figures compares two popular but contrasting software development methods: Waterfall and Agile.

Is this representation glamorous? Hell no, but it effectively serves its purpose.

AI Experiments

On a sleepy Tuesday afternoon, I asked the revamped Claude Design to create a visually pleasing infographic based on that table using my website's palette.

Five minutes later, voilà!

Note that Claude independently added the infographic's title and its one-sentence description. No prompts necessary. Ditto for the URL in the footer, although I can't copyright it.

Pro Tip: Limit Your Use of Cool Infographics

Claude's interpretation of my table works well, but only in the right contexts. Viewing online is one of them. For two reasons, though, I would never include it if I were writing Project Management in the Hybrid Workplace today. First, there's the aforementioned copyright issue. Second, the infographic's relative complexity would make presenting it in a 5.5" x 8.5" book challenging—and those numbers exclude margins. Brass tacks: most readers would struggle to digest it.

As always, remember your audience.

What about using it during a keynote or webinar?

Hard pass—largely for the same reasons. Speakers who present dense slides and tables often lose their audiences. (Case in point: the clueless presenter in this post.) Conference attendees are doing one of the following:

1. Listening to the person on stage.
2. Trying to absorb the content on the slide.
3. As is frequently the case, neither.

Foolish are the souls who believe audience members are concurrently reading and listening.

Simon Says

Design whatever you like using these newfangled tools, but remember your audience. Put simply:

AI doesn't change that simple heuristic one bit.

Not a day goes by that I don't noodle with artificial intelligence in some way. For example, last June, I used NotebookLM to generate two podcasts based on a chapter of Low-Code/No-Code. It also churned out a respectable book trailer based on its synopsis. The results impressed me, but AI is rapidly advancing, I wondered:

How much have AI multi-modal capabilities improved the last 16 months?

I decided to answer this question by giving a few new open-source video-creation tools a spin in Claude Code. Could they generate compelling book trailer for my latest effort, The Nine?

Let's find out.

Brag

I began with Brag. As expected, installing it was easy:

/plugin marketplace add latent-spaces/brag
/plugin install brag@brag

By way of background, I'm on Anthropic's Pro plan. To minimize the tokens required to create the trailer, I ultimately went with Brag's slim version. I then entered the following prompt in Claude Code:

Maybe a minute later, the following Brag/Claude offspring appeared on my computer:

The new Siri AI remains decidedly uneven at best. At worst, it is frustrating as hell. If I only had a nickel for every time I've seen or heard this message over the last three weeks.

Maybe Apple's is trying to boil the ocean with new Siri. A truly smart AI companion isn't impossible.

Exhibit A: Instinct.

Perhaps you've heard of it. The buzzy startup has raised funding at a $2.5 billion valuation. Instinct works inside your messaging app of choice.

I've been kicking its tires for the past week, and I'm very impressed. Instinct makes reservations and can also purchase items on its own. As you'll see below, it also monitors websites when corporations fail to provide their customers a rudimentary way to keep appraised of product updates.

Oh, Brother

Brother has yet to drop a proper macOS27 driver for my 12-year-old printer. As a result, I cannot print from apps. From the ancient company's remarkably user-unfriendly website:

Instead, I have to rely on a Band-Aid.

Why Brother doesn't let customers sign up for product updates absolutely mystifies me. After all, a simple button asking for an email address isn't a tough ask in 2026. Turns out that my first law of tech is alive and well.

Yeah, I can use Change Tower as a website monitor, but I wanted to try a new, AI-centric way. In the Apple Messages app, I asked Instinct keep an eye out on the Brother site for me:

As of now, Instinct is free—not that I expect that to last.

At least one new Safari feature compensates for the deficient Siri: Apple's browser lets create website alerts, as I've done below:

Simon Says

Will Apple will right the AI ship anytime soon? I'm skeptical. (How Siri AI launched in a state of eternal beta positively mystifies me.) Bloomberg's Mark Gurman reports that new CEO John Termus doesn't care much what others think.

I'm not holding my breath for a better Siri. Never again will I update to an Apple OS before its third iteration.

Postscript

True to form, on October 13, 2026, Instinct did something that Brother was unable or unwilling to do: it alerted me of the new driver. I can now print from any application I like.

“Any sufficiently advanced technology is indistinguishable from magic.”
—Arthur C. Clarke

It's often surprisingly easy to add something niche to your AI tool of choice. A few weeks ago, I created a restart command for Claude Code. Now that Claude mods have dropped, UI changes are even more accessible.

In today's short post, I'll explain another new tweak to my Claude Code setup.

The Problem: A Bland UI

Sometimes we all need to scroll up to previous parts of our sessions looking for information. This is particularly true during lengthy exchanges. When running Claude Code in Terminal, however, the delineation between user prompts and the AI's responses isn't always obvious. Because the default visual cues are lacking, it's easy to miss a step or instruction.

This past weekend, I decided to change that by creating a bespoke plugin.

The Solution: Adding Some Color to Claude Code

Formatting my responses differently than Claude Code's required a little back-and-forth. Ultimately, I landed on the following tweak:

Maybe you prefer chartreuse or mauve. Go nuts. I've decided to make it public on GitHub.

claude plugin marketplace add philsimon/orange-prompt
claude plugin install orange-prompt@orange-prompt

Of course, tweaks like these are just the tip of the iceberg. If you want to further customize Claude Code in your Terminal, the world is your oyster.

Simon Says

There’s never been a better time to be a citizen developer.

After years of providing a wholly deficient Siri, Apple finally waived the white flag. Its stunning deal with Google in last November represented a public admission that it couldn't independently build the contemporary AI chatbot its customers demanded. No more half measures, such as handing Siri queries off to ChatGPT. Time to rip the Band-Aid off. A new bespoke version of Gemini would power, in Apple's words, a “profoundly more capable and personal assistant.”

I expect bluster from tech companies, especially Apple. Over the past six months, I'll admit that I bought into the hype. David Pogue called it a “phone-changer” while rock star Joanna Stern described it as “very good.” Oodles of other reviewers echoed their sentiments.

I wish I could agree with these luminaries. As I'll explain in this post, Siri AI is off to a shaky start. Ditto for Apple's new operating systems.

Grievances With Siri AI

In no particular order, the redesigned chatbot is:

• Far slower than its predecessor—something that many Apple users have noticed.
• Unable to remember basic device settings. For instance, I want to send messages immediately (re: without confirmation). I've already disabled this setting on all my devices, but Siri didn't get the memo. Add this one other to the list of known bugs Apple has to fix.
• Flat-out dumb. So much for Apple's highly touted on-screen awareness.

Visual Intelligence misidentified my iPhone's Moft kickstand as a MagSafe battery from the same company. Finally, Siri AI is also inconsistent AF. One minute it will tell me my daily steps. Ten minutes later, the chatbot informs me that it lacks sufficient permissions to do so. There seems to be no discernible pattern.

Perhaps the issues stem from the fact that I'm technically still in Siri AI beta. When Apple finally removes that tag, my problems may abate.

Beyond Siri

And it's not just the newfangled version of Siri that's grinding my gears. Over the last two weeks, I've experienced the following snafus features with my Apple hardware and software.

• My iPhone typically does not reflect workouts started on my new Apple Watch and vice versa. Five minutes into a HIIT session my watch asks me if I want to start a workout.
• Speaking of workouts, Apple has let users connect their devices to gym equipment for nearly a decade. I've never felt the need, so I disabled the feature. One issue: Apple seems to forget that I've disabled the feature. Often during a class I'll receive multiple prompts to connect to my treadmill when none should appear.
• Shortcuts are a freakin' mess. Ones that seamlessly worked for years suddenly do. As but one example, you can no longer launch a workout from a shortcut.
• Continuity features have become much flakier.
• In its infinite wisdom, Apple's senior brass decided to kill the Apple Watch app switcher. (To the company's credit, Apple has recognized the snafu, and it will return soon. I'm reminded here of the Microsoft Windows 8 Start Button uproar.)
• Latency on Apple Music is absurd. Playing a song frequently results in a three- to five-second delay. (Hey, at least Apple's consistent. Strong Wi-Fi and cell connections don't seem to help.)

I could keep going, but you get my point. Even more infuriating, Apple has been promoting this year's OSs as stability enhancements and fixes in the vein of Snow Leopard.

I've logged a few of these issues in Apple's Feedback Assistant.

Seasoned techies like me know not to expect perfection from software. Still, the slew of issues I've encountered right out of the gate frustrates the hell out of folks who expect more from your products and services.

Simon Says

Get it together, Apple. Take a long, hard look at your current regression testing tools and processes. Remember the words of your iconic co-founder.

Feedback

What say you?

Claude Code continues to amaze me with its fast and furious updates. At the same time, though, it lacks certain basic capabilities we've come to expect from contemporary software. Case in point: a proper /restart command.

As long as I've been a fanboy, I've had to use the /exit command. In Terminal, I'd then type /claude to install updates and effect changes to my config.json file.

Not anymore.

A Simple Restart Command

As of today, I restart Claude Code by via a Raycast hotkey. As you can see below, I use ⇪ + R, but you can easily roll your own.

Technically, you don't need Raycast to run the script.

Since everyone should be able to restart Claude Code with a single command, I'm making the code available via GitHub.

Geek on.

In a recent post, I discussed the ever-expanding array of tools available to proper developers and their citizen counterparts. Today, I'll cover why it's imperative to understand the pros and cons of each tool.

Automating Notion Product Updates

A while back, I had built a Notion custom agent that sent the company's product releases to a simple database. (I refuse to check Twitter/X for its latest capabilities and changes.) As usual, I gave my new automated friend a playful and phonetic name.

Norm the Notion Product Update Tracker ran daily, but its token cost was considerable. (See the message in blue in the visual above.)

Rethinking My Custom Agent

I knew that there had to be better (read: cheaper) way to accomplish the same goal. In maybe 15 minutes, Claude Code helped me create a simple launchd job that replaced the Notion custom agent.

At the beginning of this year, I began my Claude Code journey in earnest. Since that time, I've used Anthropic's powerful new AI tool in more ways than I can count.

Sessions with my bestie have run the gamut. A few recent examples include:

1. Automating formerly manual processes for myself and clients.
2. Noodling with Notion Workers and MCPs.
3. Developing a new lead-gen tool based on my last four books.
4. Migrating a friend's website from Wix to easier for her to use, not to mention cheaper.
5. Creating more than 50 GitHub repos, including this cool Apple Health visualizer.

Note that I'm currently on the Pro plan.

Looking at the Data

I suspected that I initiated at least a thousand sessions and used millions of tokens during that time. I wasn't wrong.

Here's a breakdown:

Initial Thoughts

First up, I find it fascinating that I used ten times as many tokens per month from April to June as I did early on. I would have suspected a more gradual incline. As for consistency, I do monitor my token usage to avoid incurring outrageous bills.

Developers' toolboxes have never been more robust

Second, Phoenix in July is hot AF. Third, although I regularly use tokens, in some cases I'll opt for creating an API key. As I wrote recently, developers' toolboxes have never been more robust.

The Weekly Rhythm

I knew that I interacted with Claude Code far less during the weekend. Great, but how significant was the dropoff?

Not surprisingly, my Claude Code usage strongly correlates with my increased GitHub activity.

Feedback

How are you using today's AI tools? Does the actual data match your suspicions?

How many organizations and teams use both Slack and Notion?

Given the popularity of each tool, I'd bet that the number is in the hundreds of thousands. Yes, the two apps overlap to a degree, but they fundamentally do different things. Unleashing the full power of both requires two separate and recurring software licenses. Such is life in the SaaS world.

The Limitations of Slack's Free Plan

The no-cost tier packs some powerful functionality, but it also constrains users in considerable ways. Most germane here, workspace members can only access the most recent 90 days of message and file history. (For more information on Slack's message retention policy, click here.)

This restriction is anything but a minor inconvenience that annoys a few power users. On the contrary, the vast majority of the roughly 10 million Slack users pay bupkus. (It's not even close, and I suspect that Marc Benioff would love a Mulligan on Salesforce's $27.7B acquisition of the company in 2020.)

If you're currently stuck on Slack's Free plan, your options around old messages and files have traditionally included:

1. Lobbying your management to upgrade.
2. Footing the bill yourself under the radar—aka shadow IT.
3. Getting your IT department to create a fancy export routine.
4. Accepting that limitation.
5. Eschewing Slack altogether and using a minimalist Notion message board. (Here's my affordable template that does exactly that.)

In a word, eh.

Today I'm adding a new option to that list.

A New Alternative

My latest creation is the Public Channel Summarizer. It's a custom Slack app for budget-conscious organizations and teams that want to do all the following:

1. Remain on Slack's Free plan.
2. Preserve their valuable institutional knowledge in Slack in public channels.
3. Easily and permanently access that essential information in a Notion database.

Distribution

The PCS app is a fun side project—not a source of potential future revenue. (I lack any desire to set up a dedicated support URL.) As such, you won't find it in the Slack App Directory. Rather, I'm open-sourcing it on GitHub.

Do with it what you wish. If you want to rename it, restrict its channels, or change its settings, have at it.

Using the App

Once you set the PCS up, you'll see it in your workspace app directory:

Click on the PCS app to view more information about it, just as you would any with other Slack creation:

Once you've finished setting up the app for your workspace, invoke it by running the bespoke Slack command /summarize:

Hit Enter and the magic begins.

A few minutes later, voilà! The entry exists in a Notion database:

Open up the recap and you see the detail:

Speaking of Notion, you'll notice a new Worker in your workspace:

A Quick Note on Billing

Notion Workers don't volunteer their services. Putting them to work requires purchasing Notion credits. The actual number hinges on how frequently you use the app and the amount of dialogue in your public Slack channels. In other words, the PCS app means that you'll continue to pay Salesforce nothing. You will incur, however, extra Notion fees.

Simon Says

Odds are you haven't unlocked the true power of Notion. What are you waiting for?

If there is a spectrum of software, the Claude Codes of the world sit at the exciting end of it. By contrast, one would never use that term to describe an enterprise resource planning systems. It's not all about sexy, though. Good luck running a firm without reliable payroll, benefits, accounts receivable, and accounts payable applications.

I know more about ERP systems than most. For more than a decade, I made my bones as an enterprise systems consultant. New back-office systems don't implement themselves. As I write in Why New Systems Fail, organizations have always needed seasoned folks to do for this critical job. Great, but which individuals?

Independents usually possess deep domain knowledge, but CXOs tended to view them as risky because the certification game remains alive and well. As the old maxim goes, “Nobody ever got fired for hiring IBM.” A partner's letterhead provided cover in case things broke bad.

And they often did.

My ERP days are long behind me, but not much has really changed.
These implementations are still massive in scope. Expect multi-million dollar engagements, year-plus timelines, and large teams. (Ditto for delays and organizational politics.) No single person—no matter how accomplished, versatile, or intelligent—could independently handle a gig of any consequence.

The Increasing Viability of the Solo Practitioner

For the last few years, Notion has been the focus of my development efforts. The popular, incredibly powerful tool has evolved considerably since I began using it in 2020. Foolish is the soul who views it as a note-taking app.

Make no mistake, though: the most daunting Notion project is far less complicated, time-consuming, and expensive than the simplest ERP implementation. Apples and coconuts. As a result, in the Notion universe, engaging a solo developer or consultant is far more common than in its ERP equivalent. Here are five reasons that firms in need of Notion expertise may prefer to engage a skilled and knowledgeable independent over a dedicated agency.

Steve Jobs, AI, and the 100X Quote

You may have heard the old Steve Jobs' quote, “The difference between the average software developer and the best is 50 to one; maybe even 100 to one.” Whether that statement has ever held water is anyone's guess, but the following facts are indisputable:

• Not all consultants and developers are created equal.
• Rock stars who have mastered AI and other automation tools are considerably more productive than those who are still dipping their toes in the water.

Brass tacks: significant constraints always limited what even the most talented individuals could realistically accomplish. Those boundaries haven't entirely disappeared, buy they have certainly eroded in the last few years.

Streamlined Sales Process

Working with me is straightforward. I can't envision a simpler process.

Even a three-person team can confuse who is supposed to do what when.

That's not to say, though, that bottlenecks don't occasionally emerge. A great deal hinges upon the organization hiring me. Some have pulled the trigger immediately after our discovery call. Others have dragged out the process for months.

No Box of Chocolates

My clients know that if they hire me then they'll get me. That is, I'll be the one asking the questions, gathering the requirements, explaining Notion's inner workings, building the databases, recording training videos, and setting up the workspace automations. Put differently, they won't get:

• A consultancy's B- or even C-team.
• A blended group of junior developers or consultants effectively learning from their senior counterparts while on the client's dime.
• The next available consultant or, if you like, whoever happens to currently be on the beach. (Cue obligatory Forrest Gump quote.)

I've seen all of these scenarios play out first hand. Things get ugly quickly.

Direct Communication

Even at boutique firms, different layers and communication styles can complicate effective collaboration. Issues can arise when:

• A person forgets to CC someone else on an email.
• Someone fails to follow protocol.
• A key team member goes on vacation and forgets to set her email auto-responder or Slack status.
• Person X suddenly exits the organization. Critical organizational knowledge leaves as well—permanently.

In my experience, the more people involved in a project, the more problematic the communication and the greater the chance for misunderstandings.

Unequivocal Accountability

All else being equal, there's far less finger-pointing and a more intense CYA mindset at smaller firms than at larger ones. I've worked for both. It's not even close.

Don't conflate less with none, though. Even a three-person team can confuse who is supposed to do what when.

Feedback

Do recent AI advances make you think differently about hiring an expert vs. a small team?

Since I began using Notion six years ago, it has morphed in ways that no one could have ever imagined. (Such is the case with no-code tools.)

These days, I'm particularly excited about Notion Workers—specifically, their ability to sync data from third-party systems. After noodling with them for the last month, I've started to implement them for myself and my clients.

In today's post, I'll explain how I replaced an effective but relatively expensive automation with a simpler, far cheaper one.

Early Automation Efforts

By way of background, I've used Notion as my CRM for years. When someone fills out the contact form on my site, Notion automatically generates a new prospect/client record in my CRM01 database. If the inquiry is legitimate, then I emailed the person a scheduling link. When that individual booked time with me via Calendly, a little automation magic:

• Matched the existing CRM01 record (via email address).
• Created a new meeting record in the related CRM02 database. (After our call, I'd post the Zoom meeting in that new CRM02 entry and the NotionAI meeting transcriptions. In total, there would be CRM02 entry per client or prospect per meeting.)

The automated matching process worked, but it was neither terribly elegant nor cost-efficient. In its most recent incarnation, I routinely fired a Notion custom agent to see if any new client or prospect meetings appeared in my Google Calendar. If the answer was yes, then the agent created a new CRM02 record and notified me.

Brass tacks: Over the last few months, I wasted plenty of tokens. Still, it was the best I could do under the circumstances.

Changes and Savings

Not too long ago, I made two significant changes. First, I ditched Calendly for TidyCal. Second, I began using Apple Calendar in lieu of Google's equivalent.

These shifts made me ask a fundamental question: Can I improve my own internal process? Thanks to Notion Workers, I could and did.

What else can I automate?

I created a TidyCal API key and went to work with the Notion CLI and Claude Code. In no time, I had spun up a new Notion Worker and database that pulls all my TidyCal bookings. A few fancy automations do the same matching for me and alert me of new CRM02 records.

Even better, I can view and edit those meetings right from client and prospect CRM01 database records:

I suspect that I reduced my supplemental Notion charges from this automation by roughly 90 percent. What's more, the new, far smoother process effectively nullifies Notion's über annoying Apple Calendar bug. Everybody wins.

Simon Says

There are more ways than ever to automate manual processes. In the Notion world alone, adroit developers can access:

1. Integrations.
2. Custom agents.
3. API calls.
4. MCPs.
5. Webhooks.
6. Native automations.
7. Zapier, Make.com, and other third-party tools.

Collectively, the Notion developer's toolbox has never packed more power. Of course, some methods are better and less expensive than others.

The broader lesson: Just because you've already automated a business process doesn't mean that you can't do better.

For years, I struggled to find cleaning supplies in my kitchen's utility closet. As a result, I'd sometimes buy duplicate products. "I could have sworn I recently bought Magic Erasers," I'd say to myself when rummaging through cluttered shelves. Random bags and plastic cups were everywhere. A proper system this was not.

In April, the situation reached a tipping point. I recently decided to do something about it. My bestie Claude didn't disagree:

See for yourself:

Challenge accepted.

The Big Cleanup

Over the course of a weekend, I removed everything from the closet. I cleaned the shelves and laid down some black shelf liner in case of future leaks or spills. Logical sections began replacing the utter chaos I had created. I picked up some industrial sprayers and refill bottles. Finally, I installed some under-shelf rechargeable lights. Why not go the full nine?

Night and day.

Here's a photo of a newly organized closet shelf. Let's just say that it looks nothing like its predecessor.

Now I can easily locate Formula 409, granite cleaner, and whatever else I need. Why I didn't undertake this project years ago mystifies me.

A Workplace Parallel

I suspect that many small business owners, CXOs, team leads, and department heads can relate to my little yarn. They routinely struggle to find key information. Teammates sloppily enter duplicate records in systems because they can't find what they need. Automated reporting is a pipe dream. Answering simple questions takes way too much time and effort. They pay for tech they don't use—at least as much as they could.

You get my drift.

If you want some help cleaning your tech closet, let's talk.

In the course of my 30 years around workplace tech, I've learned a thing or six. I've seen more times than I can count how people, teams, departments, and organizations use and misuse systems. Most of my books address the subject in one way or another—especially my four-part series on the future of work.

Full-length, well-written texts have impacted my life in profound ways. Many of them taught me new skills, frameworks, and ways to become more effective. It's no overstatement that, without books, I would be a much different, less informed, and less productive person.

At the same time, though, even the best books aren't panaceas. They're static, decidedly non-interactive artifacts. Thanks to the rise of generative AI, however, that limitation is eroding.

Drumroll…

Today I'm pleased to announce the beta launch of the Simon Workplace Tech Assessment. The SWTA is a relatively short questionnaire that analyzes how your team, department, or organization uses them in working together.

After I qualify the respondent, I'll generate and send you a specific, 700-ish-word assessment based upon my four-part series on the future of work:

1. Reimagining Collaboration: Slack, Microsoft Teams, Zoom, and the Post-COVID World of Work.
2. Project Management in the Hybrid Workplace.
3. Low-Code/No-Code: Citizen Developers and the Surprising Future of Business Applications.
4. The Nine: The Tectonic Forces Reshaping the Workplace.

The STWA offers bespoke advice from a deep corpus of knowledge—more than 1,100 pages on workplace tech, collaboration, organizational change, cultural issues, and the future of work.

It's launching today in beta.