After unexpectedly losing the job I moved across the country for In 2015, I published an article called “Creating an Organizational Design Consulting Firm for the 21st Century.” It was an attempt to publicly articulate the kind of work I wanted to be doing - working at a consulting firm that treated organizational design as a living discipline rather than a one-time intervention.

That article did exactly what I hoped it would do. It found its way to the right person, Aaron Dignan, which led to me joining his new company called The Ready, where I spent the next decade doing almost precisely the work I described in that article.

After stepping away from The Ready in late 2025 to explore new options, I decided to run this play again and call a new shot. This time, the argument isn’t about the future of organizational design consulting, but rather why most modern organizations need to bring that capability inside.

The Missing Capability In Most Organizations

Most companies today are decent at optimizing within an operating model, but very rarely competent at evolving the operating model itself.

We have teams responsible for product, revenue, operations, people, technology, risk, compliance and every other function needed to run a given org. Every one of these functions has a legitimate claim on leadership attention and every one of them is incentivized to prioritize its own domain. Of course, each of them is led by leaders who will talk a good game about doing what’s best for the organization, but we all know that when push comes to shove, their first allegiance is usually to their area of responsibility.

Very few (yet more and more all the time!) organizations have a role or group whose primary responsibility is the care and feeding of the organization itself. Not performance this quarter, not headcount planning, not process compliance, but rather the living and breathing system itself.

This concept is called the organizational operating system -- the patterns, principles, and practices that describe every aspect of how an organization works and what it feels like to interact with it. Its structures, decision-making, patterns, ways of working, and its ability to change any of them to adapt without falling into chaos. I am talking about creating a dynamic OS where the dreaded re-org is a rarely used break-glass-in-case-of-emergency solution instead of the only tool available.

When this responsibility exists at all, it is usually thinly stretched across roles that already have full plates: the executive team, the COO, the Chief of Staff, the CHRO, the head of transformation. Everyone owns a piece of the org -- but no one owns the org as a system.

Our work At The Ready would often be focused on kickstarting this process before ultimately handing it over to an internal team to continue stewarding the work once we left. We were always adamant that there was no finish line for the type of work we were trying to do so while there was always an end date on our contract, the work of continuous evolution never ends. Unfortunately, there were many projects where even though we were obsessed with co-creating with the client and building capacity as we went, there wasn’t really a “home” for the work once our contract ended. It was nobody’s full-time work to continue stewarding what we had been doing together and that often meant it often fizzled out once we left.

“Design Once, Run Forever” is Not Modern Organization Design

For decades, organizations operated under an implicit assumption: design the org, roll it out, then let it run. Even when this worked, it only worked under conditions that no longer exist -- relative market stability, slower feedback cycles, and work that could be decomposed cleanly into roles and hierarchies that were unlikely to change much over time.

Today, those assumptions collapse almost immediately. Everything and anything that’s interesting in a typical organization tends to be cross-functional -- which means everything feels hard to do. Most orgs can’t easily metabolize cross-functional efforts so even the things that should feel easy rarely are.

But rejecting “design once, run forever” does not mean getting trapped on the re-org treadmill. Constant reshuffling is just as destructive as ossification, but it often seems to be the only available option in the organizational change playbook. Don’t like how things are going? Well, we’re just about due for our 18-month reorg and the massive disruption it inevitably creates. These are the missed opportunities - there are places to intervene and influence an OS other than the entire structure itself.

What’s required instead is a shift in posture: from organization design as a project handed to consultants or an under-resourced People team or a super-human Chief of Staff to do from the side of their desk -- to organization design as an intentionally ongoing capability.

An Internal Innovation Lab Focused On The Organization Itself

One useful metaphor may be the internal innovation lab.

Not a skunkworks for products -- a standing team responsible for researching, designing, developing, and experimenting with the organizational systems that make future performance possible.

This “lab” is:

• Building the conditions for sustained organizational excellence

• Reducing friction and organizational debt before it becomes existential

• Experimenting safely with new ways of working

• Increasing the productivity of every other team through better inter- and intra-team dynamics

• Creating playbooks and processes for smoother cross-functional collaboration

• Treating the organization itself like a product that needs iteration

In practical terms, this kind of team will work across three modes:

• Research and Sensing: Deep listening, sensing, and pattern recognition. Surfacing credible, human-centered insight about how work actually happens -- not how the org chart claims it happens.

• Testing and Design: Architecting and prototyping org-level solutions like structures, decision rights, governance models, talent systems, collaboration patterns, and service blueprints.

• Development & Iteration: Building the capabilities required to sustain those changes through leadership development, change activation, coaching, onboarding, and internal communities of practice.

The output isn’t a single reorg deck. It’s a portfolio of services, standards, experiments, and capabilities that compound over time.

A standing internal organization design team reduces the number of moments where leadership must personally intervene to resolve structural problems. Every senior leadership team I’ve ever worked with has talked about doing things to reduce escalations and almost never have I ever seen them have the capacity to change the system that is creating the need for escalations. It turns strategy into something the organization can absorb rather than something that needs to be enforced. It makes adaptation cheaper, faster, and less disruptive.

Over time, this capability compounds. Decisions get easier and coordination costs drop. The organization becomes more resilient -- not because leaders are working harder and longer, but because the system itself is doing more of the work. The best of these teams will bring sanity to the present so they can start freeing up their attention to exploring what their future operating system will need to be so they can start testing out those shifts before they become existential.

Unlocking Potential Energy is the Fastest ROI

Most organizations are sitting on an extraordinary amount of trapped potential energy. Not because their people aren’t capable or because the strategy is wrong, but because outdated ways of working, accumulated organizational debt, and brittle systems absorb an enormous amount of effort before any productive work happens.

This shows up everywhere, and you may even recognize a couple in your own organizations:

• Teams spending more time coordinating than creating

• Decisions waiting on escalations that add no real value

• Cross-functional work slowing to a crawl because decision rights and ways of working are unclear

• Talented people compensating for structural gaps through heroics

From the outside, this looks like execution problems. From the inside, it feels like exhaustion.

The important thing to understand is that this energy is already being spent. It’s just being dissipated as friction instead of converted into results. An internal organization design team only needs to unlock a small percentage of that trapped energy and redirect it toward productive ends to pay for itself.

This is why teams like this often pay for themselves faster than expected. Not because they introduce something new -- but because they stop the organization from leaking energy it can no longer afford to lose.

Why This Must Be Internal

External consultants can be useful sparks and accelerants (I know because I’ve been one for the past decade!) but they are rarely good long-term stewards because they don’t have skin-in-the-game or the deep contextual understanding of full-time team members who live and breathe the realities of their organizations everyday. I have been shown over and over, and now firmly believe, that the relevant time horizon for this type of work is far longer than what most orgs want to invest in an external consulting team.

Beyond the time component, this work is also deeply contextual when done well. It requires an intimate understanding of the organization’s history, power dynamics, narratives, and “vibes” -- the things people feel but don’t put on slides. Internal teams develop the kind of organizational fluency that makes better sense-making possible. They understand what’s being left unsaid, how informal networks actually work, how decisions actually get made rather than how the on-paper process describes, and how change actually propagates through the system.

We often tell ourselves that giving this work to an external entity to do helps mitigate the inherent power dynamics that are always lurking in organizations. I’ve come to see that consultants aren’t as neutral as they seem, as there’s always leader(s) who are paying for them, who advocate for them, and see them as (even implicitly) as being recruited into “their side.” Bringing this work inside the wall of the org does not eliminate inherent power dynamics, but  it can bring those dynamics to the foreground where they can be discussed and wrestled with more openly.

Isn’t This Just a Transformation Office?

On the surface, this can look like a more mature version of a Transformation Office. But there is a critical and fundamental difference. Transformation Offices exist to deliver specific change on a specific schedule. Internal organization design teams exist to grow the organization’s capacity to change forever.

One is temporary, program-driven, and milestone-oriented. The other is permanent, system-focused, and oriented toward reducing the need for future transformations altogether. In organizations that make this shift, change stops being something that happens to the organization and becomes something the organization can do for itself.

In some ways, I think the best Transformation Offices are the precursors to what I’m talking about in this article. A good Transformation Office understands that their job is not just ramming through the discrete projects on their docket, but integrating these changes in a way that has a chance of actually surviving and therefore generating the desired outcomes. A good Transformation Office is not just a bevy of project managers begging the organization to use a new tool, but trying to ride the waves that come with trying to steward and guide a complex organization toward a better future.

The Future of Work is Right Now

As environments become more complex, organizations need people whose only job is to help the organization increase coherence. To keep it from calcifying on one end or burning itself out on the other. This team does not replace the CEO, COO, Chief of Staff, or the People function. It does something different.

It owns the health of the organizational operating system itself -- so that every other leader can focus on results rather than constantly compensating for structural friction. In organizations that get this right, senior leaders spend less time managing around the system -- and more time using it.

I’m writing this from experience, not theory. Over the past decade, I’ve helped build and steward this capability inside fast-growing, high-complexity organizations navigating real constraints. I’ve seen what happens when organization design is treated as a living discipline rather than a single intervention -- and I’ve seen the cost when it isn’t. The conclusion I’ve come to is simple:

The next frontier of performance isn’t strategy or talent -- it’s the ability to change how you change. And that capability can only be built from within.

Context matters too much, learning compounds too slowly, and the cost of trapped potential energy is too high. If you’re a senior leader reading this, the decision isn’t whether your organization needs to change right now, but rather whether you want to build the capacity to change deliberately -- or continue paying for it indirectly through friction, burnout, stalled execution, and increasingly risky reorganizations. Organizations that invest in internal organization design teams gain something rare: the ability to change how they change.

I’m exploring my next chapter with organizations that are ready to make that investment, whether by building this capability from scratch, strengthening what already exists, or finally giving it clear ownership and mandate.

If you believe your organization’s biggest constraint is no longer strategy or talent, but the operating system that connects them, I can’t wait to talk.

Life and Work

The predominant happening in my work life in 2025 was the decision to leave The Ready at the end of October after spending a mostly happy decade there. The full story is longer and less interesting than you might think, but can most easily be summarized as “it was just time for a change.” If you read my seven year career retrospective article you can see some of the early ripples of discontent that coalesced into the decision I made this year. 

I’m still in the midst of navigating this change, as I did not have another job lined up when I went public with my decision to leave The Ready. I know my work will continue in the realm of organizational design and the broader intersection of personal and organizational development — but the specific shape it will take is still forming. I’m simultaneously exploring joining an organization to help them develop internal capacity for organizational design and change while also exploring shorter-term projects under the banner of my own company, Deliberate Works LLC.

While the decision to leave The Ready was made in October, the whole year up to that point was marked by a higher than normal amount of stress. A casualty of that elevated stress level was my triathlon training. I had originally planned to do a local half-Ironman as my only race of 2025, but around July I made the decision to withdraw and abandon my dedicated training. What was supposed to be an outlet and stress-reduction activity had subtly turned into another job that I was doing poorly. I found myself getting behind the training plan which meant the predominant feeling after every training session was something like, “Ugh, I’m not where I should be.” I needed to remove stressors from my life, not add them, so I decided to put the triathlon-specific training on the shelf.

In its place, two new practices have re-emerged: walking and weightlifting. Most days I walk for 45-90 minutes and I’ve been lifting several times a week for the past couple months. It has been nice to let myself do (mostly) what I want to do rather than feel like I should be doing something extremely proscribed all the time. And, wouldn’t you know it, once the looming threat of a race I was unprepared for was removed from my calendar, I’ve found myself wanting to get back on the bike and put the running shoes back on (I can’t say I’ve been craving getting back into the water though…)

Somewhat surprisingly, I’m fairly certain that this relatively short but consistent time of lifting again has resulted in me being the strongest I ever have. I don’t have any records from my college days, but I don’t have any memory of having lifted what I’m currently lifting. Not much to write home about for most, but it has been gratifying to see all of those numbers gradually go up. 

As a bit of a replacement for my paused triathlon training, I devised a little project for myself I’m calling “FIT40” which is simply the intention to achieve a handful of objective strength, cardio, and health measures by the time I’m 40 (February 2027). I will likely write more about this in the coming year as I continue to refine those goals and how I intend to get as close to them as possible.

A quick grab-bag of additional events and moments from this year:

• Getting more involved in the care of my nephew who was born with an extremely rare neuromuscular genetic disorder called RYR-1

• Meeting another nephew who was born in February

• Moved into a new apartment (down the hall from our previous apartment)

• Travel to San Jose, Buffalo, Oakland, and Cape Cod for work and family reasons

• Traveled to Ireland for a family wedding and short vacation

2025 was an extremely unsettled year when it comes to my professional life — but has ended on a high note with the optimism that comes with exploring new opportunities. Life-wise, 2025 continued to bless me with loving family and friends.

Reading

In 2025 I read 63 books across 23,138 pages. This is the most I’ve read since 2018 and the fourth most pages I’ve read since I started tracking in 2008. 71% of the books I read were non-fiction. I haven’t done the math, but I imagine it actually looks more like 60/40 non-fiction/fiction if you do the calculation via pages, because there were a few absolute fiction-chonkers this year (e.g. Wind and Truth, Anathem, and Crime and Punishment).

I don’t want to do a completely exhaustive retrospective on the year, so instead I’ll pull out a few notable observations and recommendations. My favorite non-fiction books from the past year were Things Become Other Things by Craig Mod, Apple in China by Patrick McGee and The Sirens’ Call by Chris Hayes. I can picture TBOT and The Sirens’ Call being books I re-read at some point in the future (in some ways, TBOT was already a re-read because I read the original fine art edition of the book Craig put out in 2023 when it was first published).

My favorite fiction from the year was The Etched City by K.J. Bishop, On the Calculation of Volume (Book 1) by Solvej Balle, and Anathem by Neal Stephenson. All three of these books grabbed me like little else ever has and were more or less complete surprises. I had very little expectations about any of these and all of them completely engrossed me.

18 of the 61 authors I read this year have written something I read in a previous year. That means I read 43 authors for the first time this year. A few authors showed up more than once this year: Solvej Balle (two), Cormac McCarthy (four), Tom Holland (two), Dan Jones (two), Katherine Addison (two). 

If I had to pull some themes out of this year, the following stand out:

1. I’m interested in systems under strain: Across politics, technology, organizations, and the self, I keep returning to moments where systems drift, harden, or collapse — macro systems (Autocracy, Inc., Technofeudalism, Dominion, Apple in China, Who Is Government?, The Wars of the Roses), tech-mediated systems (Nexus, Enshittification, Superbloom, The Sirens’ Call, Extinction of Experience), organizational systems (The World Is Your Office, Leading into the Age of Wisdom, Bonfire Moment, How to DAO), or inner systems (The Burnout Society, The Anxious Generation, Meditations for Mortals, Zen Mind, Beginner’s Mind).

2. I’m interested in attention, meaning, and limits: I’m obviously skeptical of the modern myth of infinite optimization. Meditations for Mortals, The Burnout Society, The Anxious Generation, Superbloom, The Sirens’ Call, Excellent Advice for Living all form a loose canon about attention as the scarce resource and limits as something to be designed with, not escaped. Even this year’s fiction echoes this: Invisible Cities, The Lathe of Heaven, On The Calculation of Volume Part 1 and Part 2, and the Border Trilogy by McCarthy all dwell on constraint, repetition, silence, or inevitability rather than progress narratives.

3. I’m drawn to threshold moments: Many of this year’s books sit at edges: collapsing empires (McCarthy’s Border Trilogy, Young Men and Fire, The Wager), technological inflection points (Masters of Doom, Nexus), moral or metaphysical thresholds (Crime and Punishment, Arendt, Foucault, Dostoyevsky, Schopenhauer, Spinoza). What do people do when old maps stop working? How do character, structure, and belief interact when the rules no longer feel trustworthy?

Finally, I’ll say a few words about how I manage to read this much. I don’t offer this as any sort of judgment about how much you read (or didn’t) last year, but only because it’s the number one follow-up question people seem to have when I let slip the number of books I read in a year. Take what’s useful, discard the rest. 

First, a few structural realities/privileges that help me read a lot that may or may not apply to you: I don’t have children, I read fairly quickly, I mostly work from home, and I have access to many books via disposable income and a great local library. 

Moving into the more actionable patterns you might be able to do something with: 

1. I always try to have one book going in each of the following formats; paper, digital (Kindle and/or Apple Books), and audiobook (Audible and/or Spotify and/or Libby). This means there’s very rarely a context where I can’t read because of a lack of access. I can (and do) read digital books on my phone. I will listen to audiobooks while I work out or drive (and don’t let anyone ever tell you that audiobooks don’t “count”). 

2. This may seem counter to what I just said about having at least three books going at once, but I also try to limit the number of books I read at the same time. Usually not more than three, never more than 4 or 5. I will try to read these books as a pack — meaning I won’t let myself start a new book until I’ve finished the whole set of 3-5. That means sometimes I have to “make” myself finish the last one (usually the one I’ve been avoiding for some reason) in order to “unlock” the ability to refresh my stack. I hold this lightly which means sometimes I’ll immediately replace one I finish even if I’m still working on the others in the “set.” And sometimes not. 

3. I think it’s helpful to have different “types” of books going at the same time so that if I don’t feel like reading one thing there’s a chance I’ll feel like reading something else (again, I’m aware of how this is at odds with the “limit WIP” pattern I describe in the previous paragraph). That might look something like having one “work” book, one classic literature, and one sci-fi. Or maybe two non-fictions about wildly different topics and one fiction. You get the idea. If something isn’t grabbing me at any moment in time I can always shift to something else. 

4. It can be useful to think of part of your reading practice as “attention training.” That means I periodically try to read something I know I won’t understand or is “too hard.” It’s okay if I don’t understand it completely. I think it’s valuable to regularly sit down and put your attention on something difficult. I generally won’t read books like this back-to-back but at least a couple times a year I want to be a little bit intimidated by what I’m trying to read. I trust that this has value for my ability to focus beyond the specifics of any one book.

5. Finally, my last pattern is to not stress out about it. I don’t read this much because I’m trying to hit some kind of arbitrary number. I read this much because this is how much I want to read. It’s my favorite entertainment activity and what I find myself drawn to whenever I have downtime. The end result is I typically read 50-60 books in a year. There have been seasons where I’ve read less than this and there may be future seasons where I read drastically less than this. I’m okay with it. Reading should be fun. Don’t stress yourself out over it.

Other Entertainment

TV

I watched 13 seasons of television across 9 shows this year. This is pretty similar to the amount of TV I watched in 2024. The only show I watched multiple seasons of was Drive to Survive, where I made it through the first five seasons of the show. Five shows were me watching the latest available seasons: Severance, Andor, Shrinking, Foundation, and Slow Horses. One season was a straight-up rewatch: Band of Brothers (Emily is on a military history kick and hadn’t seen it before). The new shows were Pluribus and Drive to Survive. I watched part of the first season of A.P. Bio but ended up dropping it after a few episodes.

When I look back at the year of TV I’m struck by how there’s SO MUCH great TV that I’m not watching, but want to. The stuff I did watch, though, was really good. Severance, Andor, Shrinking, Foundation, and Slow Horses were all excellent — with Andor probably being the single piece of video that made the biggest impact on me this year. 

Film

In 2025 I watched 12 movies, which is five more than I watched in 2024. I thought I was going to be on track for basically the same as 2024, but experienced a veritable onslaught of movie watching in the last two months of the year, with one in November and four in December. I mostly enjoyed everything I watched, with maybe The Phoenician Scheme being my least favorite. I think Wes Anderson figured out how to be too Wes Anderson. And yes, I’m naming it as more disappointing than Jurassic World: Rebirth because my expectations were non-existent for the dino movie and it actually mildly exceeded that exceedingly low bar!

We went on a semi-accidental Russel Crowe binge after really enjoying Nuremberg so we obviously had to follow it up with Gladiator and Master and Commander: The Far Side of the World. 

I watched Rogue One (a re-watch) immediately after finishing the last season of Andor and it felt like it added a bunch of emotional weight that wasn’t there the first time I watched it. My lovely wife is the reason we watched Apocalypse Now this year (a re-watch for me) because of the aforementioned military history kick she has been on.

Video Games

In 2025 I played seven video games for a substantial amount of time (at least a few hours) and beat five of them: Inscryption, Bioshock, Final Fantasy VII Rebirth, Hollow Knight, and Silksong. I would call both Hollow Knight and Silksong truly transcendent video game experiences. Both are now in my top five favorite games of all time and consistently evoked feelings of wonder, awe, and deep emotional resonance as I played them. Final Fantasy VII Rebirth was also surprisingly good, especially since it is a remake of my favorite video game of all time which can be fraught territory.

I really leaned into the idea of only playing one game at a time for the majority of the year. I’ve learned that the types of games I like to play really benefit from the familiarity and skill development inherent in not letting too much time elapse between play sessions (all you Hollow Knight and Silksong fans just said, “Yeah, no shit.”) I like games that require you to continuously improve your physical skill and that reward your ability to learn their worlds in a way that you can’t if you’re only playing them once every couple weeks. This is likely something I’ll carry into 2026, too.

Music

Music is almost always a tool for me. Meaning, I primarily listen to music while I’m working or writing. Which isn’t particularly conducive to really appreciating what it is I’m listening to. This is also why I sometimes don’t recognize a couple of my most played artists in my end of year streaming wrap-up because I spent most of my time listening to playlists I didn’t make. That being said, I can almost always count on Coheed and Cambria showing up somewhere in my top five, like they have for at least the last decade. And, in a repeat of 2024, Petey was once again my most listened to artist of the year. Can’t get enough of my angsty and absurd boy.

Other Entertainment

It was a light year for live entertainment and probably would’ve been even lighter if I wasn’t married because I was not the driving force behind either of these outings. I saw Nine Inch Nails live because Emily really wanted to. I really only know NIN via listening to the radio in the late 90s and early 00s, but the show was surprisingly good. 

And maybe my most memorable entertainment moment of the year, I saw the musical Titanique! with exactly zero foreknowledge about what it was. I knew the Titanic was involved… and that’s it. To say I was impressed and surprised would be a huge understatement. Highly recommended, would see again.

Does going to a book signing/author talk count as a live event? Let’s say yes, which means I can throw seeing Craig Mod in Beacon, NY with my brother into this category as well. His Things Become Other Things book was one of my favorites of the year and it was cool to share physical space with him for an evening.

Software & Hardware

You could read my 2024 Hardware & Software review articles and they would be 95% accurate for what my 2025 consisted of, too. There were no notable changes to my hardware setup this year. I’m still rocking the same M3 MacBook Air, M4 iPad Pro, iPhone 15 Pro Max, old-ass HP monitor, older-ass Aeron Chair (that I did have to amputate the arms off of this year…), and everything else I listed in last year’s article. The only new things involve a slightly better webcam than what I had before (because Jack got tired of editing my janky video for At Work with The Ready), and some fancy Studio Neat Mark One pens.

I noticed some burn-in on my monitor for the first time a few weeks ago, so I’m wondering if that is a precursor to something more catastrophic happening sooner rather than later. I’m hoping it can hold on long enough until Apple updates their display product line. By the time next fall rolls around, I’ll be rocking a 3-year old phone so I would imagine a new one might be in the cards by then. It’s still chugging along just fine, though, so I’m gonna try to keep it going as long as is reasonably possible. 

Things are almost as static on the software side of the house, too. The major changes are casualties of no longer being employed at a company that expects me to use certain tools. I’m spending much less time in Slack, Notion, and Loom. Sadly, my Superhuman account expired shortly after my employment at The Ready ended and I can’t justify dropping hundreds of dollars on an email app, as much as I enjoy it. I’ve replaced it with Airmail for the time being, but have also used the default Mail app in its place.

The core of my productivity stack has remained the same, as it has for probably the last decade or so. Things, Fantastical, Bear, Ulysses, Day One, Overcastare still the apps I spend the most time in. ChatGPT remains my default LLM but I’ll occasionally dip into Perplexity or Gemini to compare/contrast. I’m switching back and forth between Arc and Safari as my mood dictates. I’ve tried most of the AI browsers for a hot minute and so far have not seen the light in terms of what they are bringing to the table.

I started using an app called Strong again to help me keep track of my weight training progress. I first used it many, many years ago and it is still really good. I’ve been pleasantly surprised how well it has been maintained and how easy to use yet full-featured it is. My favorite piece of new software this year is probably Monarch. I used to be a pretty deep user of Mint, back before Intuit bought it and destroyed it. I took the time to get fully set up into Monarch in the middle of the year and it has helped me get my arms around my finances in a way I didn’t really realize I was missing until I started using it. It’s a surprisingly delightful piece of software.

Conclusion

What should be gleaned from this year? A year that contained some of the most monumental changes I’ve experienced in years (leaving The Ready, stopping triathlon training) along with pure stability in others (hardware, software, how I allocate my entertainment attention). Perhaps the stability I seek in many aspects of my life is what gave me the foundation to have the clarity and confidence to make some of these large changes? Or perhaps I revert to familiarity when other aspects of my life feel out of control? In all likelihood, it’s probably a little of both and neither. 

Previous Yearly Review Articles

• https://www.samspurlin.com/blog/2024-year-in-review-entertainment

• https://www.samspurlin.com/blog/2024-year-in-review-entertainment

• https://www.samspurlin.com/blog/2024-year-in-review-training

• https://www.samspurlin.com/blog/2024-year-in-review-software

• https://www.samspurlin.com/blog/2024-in-review-reading

• https://www.samspurlin.com/blog/what-stayed-the-same-for-me-in-2023

• https://www.samspurlin.com/blog/2022-state-of-the-sam

• https://www.samspurlin.com/blog/state-of-the-software-2022

• https://www.samspurlin.com/blog/2021-in-review

• https://www.samspurlin.com/blog/2020-writing

• https://www.samspurlin.com/blog/looking-back-at-a-year-of-growth-grief-and-calm

• https://www.samspurlin.com/blog/looking-back-at-2018

• https://www.samspurlin.com/blog/state-of-the-apps-2018

• https://www.samspurlin.com/blog/186

• https://www.samspurlin.com/blog/2017-books

• https://www.samspurlin.com/blog/2016-podcast-review

• https://www.samspurlin.com/blog/2012-on-the-website

• https://www.samspurlin.com/blog/2012-state-of-sam

Tech and Work

I was fortunate enough to have a few significant upgrades in my most frequently used hardware this year. I was eligible to upgrade my work laptop and went from a M1 MacBook Air to a M3 MacBook Air. I stayed at the 13-inch size because it’s mostly closed and connected to an external monitor when I’m at home and when I’m traveling I want it to be as small as possible.

I used a big chunk of our credit card points to get a new M4 iPad Pro 12-inch with cellular, a Magic Keyboard, and Magic Pencil. This is the first “normal” sized (i.e. non-Mini) iPad I’ve owned in a few years and I’m using it as my personal device since I’m trying to create more of a firewall between my work device (the MacBook Air) and my personal devices (the iPad Pro). I ended up trading in my refurbished iPad Mini earlier this year because I found it frustrating to use because it had such little storage and its performance seemed strangely bad compared to what I was expecting. I’m loving having a powerful device with a cellular modem. There’s something really liberating about not needing to hunt for wi-fi when out and about.

Other than the computer, there are no significant changes to what sits on or near my desk. I still look at a 27” 4K Z27 HP monitor all day every day and the same Logitech BRIO webcam sits on top of it. I still use a Magic Keyboard and Magic Mouse as my primary peripherals when I’m sitting at my desk. I still have a Shure MV7+ USB mic on a boom and an Elgato key lightto make me look and sound good on podcasts and video calls. No changes to my nearly decade-old Fully Jarvis sit/stand desk or Herman Miller Aeron chair despite moving this year. If I wasn’t on a podcast I’d be able to massively simplify this desk setup. I think this is as simple as I can make it while still being able to record the quality of audio and video we need for At Work with The Ready.

At the end of 2023 I bought a set of AudioEngine A2 desk speakers because I got tired of trying to use my original HomePods as computer speakers. The HomePods are still in my office but are mostly just there to fail at my verbal Siri requests instead of failing at playing audio from my computer.

I didn’t upgrade my phone this year so I’m still rocking a case-less and mildly cracked iPhone 15 Pro Max. No changes to my daily headphones, AirPods Pro. The AirPods Max are still hanging around but mostly only get used as airplane headphones when they aren’t hanging from a hook under my desk. My daily (and training) watch continues to be the Apple Watch Ultra 2 with cellular.

This year I re-discovered the joy of index cards. I keep a stack of them on my desk and just whip through them any time I feel the need to jot something down or keep my hands busy during a meeting. I have the same brass pen on my desk that I’ve had for years. It’s hefty, takes Pilot G2 refills, and feels great in my hand. I do almost everything digitally nowadays, so I think I’ve been on the same medium, hardcover Moleskine notebook since the end of 2022. It stays on my monitor riser during the day and I make sure to always have it with me when I travel.

Entertainment

Entertainment hardware basically stayed the same except for one extremely significant exception: a new TV. I took advantage of a good Black Friday sale to pull the trigger on a 65” Sony BRAVIA XR A95L OLED TV to replace the 55” TCL we had since early 2018. It’s still early days but it seems like a remarkable piece of hardware.

Everything connected to it, a Sonos Playbase, two Sonos Play 1s, PlayStation 5, Nintendo Switch, and Apple TV 4K remain unchanged.

There was actually another TV purchase made this year, but it was much less exciting. In an effort to spruce up my indoor riding situation (as mentioned in my 2024 in Review: Training article), I got a cheap 32” Samsung and put it on a rolling cart with another Apple TV 4K as my dedicated Zwift machine. It is helping to make indoor riding slightly more bearable.

I’m still rocking two original HomePods in my office and two HomePod minis (one in the bedroom and one in the kitchen). They are primarily used for getting frustrated with Siri and sometimes playing very nice audio.

I still do most of my non-iPad or non-iPhone digital reading on a Kindle Paperwhite.

Training

2024 marked my third full year of training for triathlons and the vast majority of my equipment has remained unchanged from the original equipping I did in the summer of 2021. I’m still rocking the same mystery year, Craigslist-attained, Trek Madone road bike with aftermarket aerobars, a Garmin Edge 530 head unit, and Garmin Forerunner 745 watch. The watch, somewhat interestingly though, has mostly lived in a drawer as I’ve learned I can use my Apple Watch Ultra 2 as my everyday watch and training watch. I even wore it during my half Ironman race this year and it had plenty of battery to get through the whole 6+ hour race. The other piece of kit that has mostly lived in a drawer this year is my Apple PowerBeats Pro headphones. These are my go-to headphones to wear when riding outside because it’s impossible for them to fall off but I’ve done much less of that this year. Riding indoors, running indoors or outdoors, and strength training all happen with my AirPods Pro.

I still do the vast majority of my running in On Cloudmonsters. I wear Pudolla running shorts, Amazon Basics tech t-shirts, and the running hats given as part of participating Ironman Michigan 70.3 the past two years. I’ve got Baleaf swim jammers, a Speedo pull buoy, some Omid goggles, and Speedo swim caps. I actually have two pairs of flippers because I thought my original pair didn’t make the move from Arlington, but apparently they did. I have the same basic Shimano cycling shoes I’ve had since the beginning. My Saris bike rack for my car continues to be a stalwart (it was stolen off my car in 2023 and I re-purchased the exact same model).

As mentioned in the previous section, I upgraded my indoor riding room by getting a TV and an Apple TV 4K to give me a better setup for using Zwift. Another part of that upgrade was replacing my Kickr Snap with a Kickr Core. I also bought an Amazon Basics weight bench to keep in that room and it primarily serves as a table for my nutrition during long rides. A generic music stand does a good job of holding my iPad and phone within arm’s reach while I’m riding.

A few other fun upgrades this year was getting a Giro Aerohead MIPS racing helmet and a new Cannondale Topstone gravel bike. I live within easy riding distance of an approximately 9 mile gravel trail that tracks along the Hudson River so I wanted to get something that would let me ride it, especially since I’m pretty sketched out about riding on the roads around me. I also picked up some On carbon-plated shoes to wear during my race, but I got cold feet about actually wearing them for my half Ironman this year since I hadn’t yet done a long run in them. They will be waiting for me next year, though. I don’t think I’d call a new heart rate monitor a fun purchase, but I did have to replace my original Garmin this year and I decided to go with a Wahoo Tickr. My racing kit — one of the development team fundraiser options from That Triathlon Life — was new this year and made me feel faster than I am. My second pair Goodr sunglasses finally de-laminated so badly I couldn’t see out of them any more, so I got a pair of Tifosi’s for my outdoor cycling needs.

Kitchen

No major changes in kitchen kit this year. I remain the primary chef for our family and more or less have everything I need to handle cooking for us.

Starting in roughly chronological order of when I interact with these tools, my coffee setup remains anchored by my Fellow grinder and electric kettle. I get my beans delivered on a schedule from Trade Coffee (use this referral link if you check it out and I’ll get some free coffee) and generally alternate between AeroPress and pour overs, depending on my mood. I have a multi-cup Chemex that I don’t think I used once in the past year, but keep handy for any situation where I need to make coffee for more than just me. There’s also an espresso machine Emily gave me last Christmas, but it’s more for afternoon snacks. In the morning, I’m a simple pour over or AeroPress guy. The Eufy handheld vacuum stays right next to the grinder and kettle and is extremely necessary for cleaning up my coffee grinding mess.

Our Aarke water carbonator gets a lot of work and we keep it supplied with CO2 via a subscription from SodaSense. Our KitchenAid stand mixer is always ready for me to whip up some bread dough or cookies. Our Breville 650XL toaster oven is a total champ (thanks to John Siracusa for the recommendation). Our Vitamix remained underused this year, as Emily has seemingly moved on from her smoothie phase and I keep thinking about making soup in it and then not doing so.

A Belkin charging stand lets us use our phones in Standby Mode while we’re doing things in the kitchen. Our Frigidaire dehumidifier makes sure the apartment isn’t getting weirdly humid. There’s a pizza stone living in the oven — ensuring we’re always ready to make some bread or a pizza. Deli containers are our go-to leftover containers of choice and my Zojirushi travel mug is always standing by waiting to keep my coffee hot for an unnaturally long time.

My knives aren’t particularly noteworthy, other than the fact that I try to keep them all extremely sharp with a nice whetstone session every couple months or so.

Clothing

Some expensive shoe purchases over the past few years are coming to fruition this year in the fact that other than some new running shoes, I didn’t have to buy any other shoes this year. I’m still rocking Wolverine boots from 2018, Rothy’s sneakers from 2022, Velasca sneakers from 2020, Velasca dress shoes from 2021, Teva flip-flops from 2018, Glerups from 2021, and some brown BEDSTU shoes from at least 2018. I was tired of buying shoes that fell apart after a year and were impossible to repair.

I don’t generally think about my clothes very often because I tend to wear the same thing over and over, but this year did result in me changing two staples pretty significantly. After many years of wearing Everlane t-shirts, I got frustrated with their worsening quality and decided to find a new default shirt. I landed on Uniqlo for awhile, but they were somehow too nice? At least, they were too thick. I then stumbled across the Comfort Colors brand in some random article and they’ve become my new default shirt. Cheap and soft and pretty nice fitting.

I went on a similar journey for new socks after wanting to move on from the Everlane/Aasics combination I had been rocking for the past few years. I ended up going with Darn Tough in two different varieties: ankle socks and mid-calf socks. I’m learning to quiet the Millennial voice that yells at me every time I wear socks that extend beyond my ankles.

I had to get some new sunglasses this year after breaking my previous pair and decided to go with some custom RayBan Wayfarers (got them with orange arms and blue frames, which looks good with my orange strapped Apple Watch Ultra 2).

Odds and Ends

A few other significant additions this year include a new Roomba i3+ EVO robot vacuum and a (new to us, but used) 2014 Subaru Forester. When we moved to New York we needed a second car since Emily commutes to an office every day in our 2020 Toyota Camry. I bought a ridiculously expensive, but really good, phone mount for the Forester and now it’s basically perfect for what I need it to do.

A few old stalwarts worth mentioning include maybe the oldest piece of tech I own, a Coway air purifier from 2016 that lives in our bedroom. My Wahl beard trimmer is also still going strong from 2017.

Looking Ahead

Despite this being the longest article in my 2024 Year in Review series, I didn’t actually buy many new physical items this year. I’d definitely like to keep that trend going in 2025. Moving has a way of really clarifying how much stuff you have in a really visceral and annoying way, so even though we don’t have any imminent plans to move again, there’s definitely a non-zero chance we could move again sooner rather than later and I’d love to not live in fear of that possibility more than I have to.

Video Games

It’s funny, I self-identify as a “gamer” and spent most of my childhood pining for the games and consoles I couldn’t afford, but I actually played objectively few video games this year. The only game I fully completed was Final Fantasy XVI, but I played the bulk of it in 2023, only putting the finishing touches on it in 2024. I haven’t touched the DLC, yet, but I plan to. Continuing the Final Fantasy theme, the game that consumed the majority of my playing time this year was Final Fantasy VII: Rebirth. It’s a marvel of a game, truly. The original Final Fantasy VII is my favorite game of all time, searing itself deep into my childhood and teenage subconscious. Somehow, they’ve created a game that has honored that hyper-nostalgia without just making a frame by frame remake. I’m enjoying it. Haven’t finished it yet, but hopefully in the first half of 2025.

As far as additional console gaming goes, I played some Helldivers 2, Hollow Knight, and Inscryption. Playing games with strangers stresses me out, so Helldivers 2 ended up on the shelf pretty quickly. I started scratching the surface of the beauty and stellar reputation of Hollow Knight, but hit a couple of spots that demoralized me so completely I put it down to take a break, and then several months had elapsed. I only started playing Inscryption in October, and I’ve liked it quite a bit.

Outside my PlayStation, I’ve dabbled in Finity, Vampire Survivors, and Balatro on my iPhone, with Balatro taking the majority of my attention there.

Music

Music is almost always a productivity tool. I turn it on when I need to focus, which means I listen to almost exclusively instrumental tunes. I also rarely listen to albums, choosing to stick to playlists like Apple’s Chill, Focus, Lo-Fi Japan, Living in the Library and other downtempo/electronic playlists. Tycho is the epitome of the music I’m looking for when working, and there was actually a new Tycho album, Infinite Health, this year that I found myself listening to on repeat for a while.

Other than music-as-focus-tool, my big discovery this year was Petey. I got obsessed. In a true sign of the times, I first became aware of Petey because of his absurd sketches on Instagram. I then heard his music referenced by the triathlon podcast I listen to, so I decided to give him a try. Oh man, it scratches the same itch that Manchester Orchestra and Say Anything and Modest Mouse do for me. Plus, he has connections to Michigan (gotta appreciate any time someone wears a Detroit Vipers jersey). It’s rare when I find a new artist (to me) and they almost immediately pop into my top five favorite artists list, but Petey did it.

Honorable mentions have to go out to everyone’s favorite German partycore band, Electric Callboy, who I continue to adore and their collaboration with Babymetalthis year is a delight. I started to dabble into some seriously heavy stuff like Lorna Shore thanks to my strange obsession with watching drummer YouTube videos as a non-drummer (shout out to Drumeo, for that). Sometimes you just wanna listen to some insanely talented musicians shred and growl like demons, you know?

Oh, and my favorite band of all time, Coheed and Cambria, has been releasing some new singles (and a whole album of covers), so you know that has me looking excitedly toward 2025.

Movies

Boy, I certainly don’t watch many movies, eh? I watched a grand total of 7 this year. Godzilla Minus One, Perfect Days, Gettysburg, and Dune: Part Two fwere great. Furiosa: A Mad Max Saga was okay. Napoleon and The Creator were bad.

TV

I watch only slightly more TV than I do movies, but the overall hit rate on what I watched this year was much higher than past years. The entire run of Detroiters (S1 & S2), Shoresy (S1-3), The Last of Us (S1) and Slow Horses (S1-S3) were incredible. Fallout, 3 Body Problem, Faceoff: Inside the NHL, and Planet Earth III were pretty okay. Not a fan of The Mandalorian and don’t think I’ll be moving beyond the first season.

I’ve also come to enjoy Dropout TV, particularly the show Very Important People. Two comedians sit down for an improvised interview after one of them receives an elaborate makeover and has to make up a character to go along with it. Some episodes are whiffs, but the ones that hit, hit hard.

There are a few YouTube channels where I generally watch every new video: the boat building-turned-boat-sailing channel, the long-haul hiker who posts daily recaps, the aesthetic triathlon channel and the unhinged but motivating triathlon channel, and a couple of hockey recap and analysis channels.

Podcasts

The champion of 2024 was, by far, The Rest Is History. After hearing people praise it, I finally went face down in it this year. It’s incredible and maybe my new favorite podcast.

I’m not a huge 99% Invisible fan, but their yearlong read along of Robert Caro’s The Power Broker with Elliot Kalan from The Flop House was great. They had some great guests, including what felt like out of nowhere, Brennan Lee Mulligan from Dropout.

The current full roster as of December 31st, 2024 is: The Rest is History, Accidental Tech Podcast, Philosophize This!, 32 Thoughts, Upgrade, Reconcilable Differences, Dan Carlin’s Hardcore History, Dithering, Sharp Tech, Sharp China, In Our Time, Coretex, Navel Gazing, Robot or Not?, Roderick on the Line, The Talk Show with John Gruber, That Triathlon Life Podcast, Under the Radar, The Vergecast.

And I’d be remiss if I didn’t mention the podcast I co-host, At Work with The Ready, even though I have trouble listening to it since I put so much time and attention into making it.

Other Entertainment

2024 was a weirdly sporty year for me. I got into F1 thanks to finally cratering to peer pressure (many years later) on Drive to Survive. I picked up the F1 season about halfway through the summer and watched every race from there until the end of the season, developing the appropriately strong opinions about things I barely understand along the way.

Early in 2024 the extremely mediocre Detroit Red Wings, my favorite team of my favorite sport, went on a bit of a run at the end of the season and almost made the playoffs for the first time in the better part of a decade. Alas, they did not. But it was exciting for a while. Don’t talk to me about this season, though.

Similarly, the Detroit Tigers went on a perhaps even more improbable run at the end of last season, did make the playoffs, and got closer to making the World Series than anybody expected.

And just to round out my sporty year, the Detroit Lions are finally good and after years of heartbreak and then mostly ignoring them, I’ve tried to watch the vast majority of their games this season.

If I had to give my 2024 triathlon training efforts a grade, it’d be a solid B-.

I cycled and swam significantly less than I did in 2023 and 2022, but I managed to run and walk more. My training consistency took a bit of a hit with the upheaval of moving from Virginia to New York, but never completely fell off the rails. I learned how important it is to have Default Run and Default Cycling routines (the running or cycling route you take when you don’t want to think at all about your running or cycling route). When those need to be recreated from scratch in a new location, you can be left feeling a bit unmoored until you’ve landed new ones.

In 2024, I completed 541 miles of running across 106 hours and 4 minutes. In 2023, I did 528 miles and 470 miles in 2022. Moving to the Hudson Valley has helped with this because my new Default Run is on a dirt path along the Hudson River, not the sidewalks of Arlington.

In 2024, I only completed 55,144 yards of swimming, down from 95,350 in 2023 and 98,917 in 2022. This is where my move from Arlington worked against me. In Arlington, I was mostly swimming in a beautiful aquatic center within walking distance of my apartment. In Haverstraw, I’m swimming in a relatively dank gym pool a fifteen-minute drive away. I also did some organized open water swims with my coach when I lived in Virginia, but I didn’t manage to swim outside (apart from my race) once in 2024. This is something I need to fix in 2025.

I cycled for 2,170 miles in 2024, down from 2,236 in 2023 and 2,534 in 2022. Again, this is where my move has complicated things. When I lived in Arlington, I could ride from my front door to a couple different rail trails where I didn’t have to worry about cars. That’s not really the case in Haverstraw. I can drive to Harriman State Park with my bike and do some beautiful (and hilly) rides in relative safety there, but I’m extremely skeptical about riding on the roads near my apartment.

I was already kind of anxious about road riding, and then the Johnny and Matthew Gaudreau tragedy happened over the summer, and it sketched me out even further. To counteract this, I let myself invest in improving my indoor riding setup this fall in hopes of not letting that affect my training too much. I also bought a gravel bike in October so I could start riding the trail I mentioned earlier.

When I set up my race schedule for 2024 I didn’t know I was going to be moving to New York. That meant the two Virginia races I scheduled because they were convenient suddenly became very inconvenient. I bailed on both and ended up only doing the Michigan 70.3 in September. This was my second time doing the race, so it was nice heading into it knowing what the course was like and how to handle all the logistics.

Remember how I said I didn’t do any open water swimming this year? Yeah, it showed up big time in this race with some mild panicking early in the swim, but eventually calming down and finishing it without incident (but slower than 2023). I was determined to do something better than the year before, so I focused on going hard (probably too hard) on the bike and ended up improving on my 2023 time by at least fifteen minutes. The run, though, was back to disappointment as I paid for my exuberance on the bike by just absolutely death-marching the admittedly much hotter than expected run to a significantly slower time than 2023.

Looking Ahead to 2025

Now that we’re settled into our new place in New York, I’m excited about a less disrupted year of training. I’d like to sit here in a year and report that I had my biggest year of training ever. I’ll need to figure out the open water swimming situation (I’ve got my eye on a couple of options, and it’s unfortunate that having a river in my backyard hasn’t made this simple) and figure out how to balance the soulcrushingness of indoor cycling with the danger of riding outdoors, but I’m feeling optimistic I can have a good year.

Regardless of how the year goes, trading the miserable Arlington, Virginia summer for the cold and hills of the Hudson Valley is a net-win, in my book.

Communication

Superhuman remains my email client across all devices. It’s ultra fast and allows me to use keyboard shortcuts without modifier keys (i.e. just hitting “E” to archive a message, hitting “C” to start a new email, etc.). That being said, I did spend some time with Apple’s Mail apps this year with very little interruption to my workflows. I don’t like the Archive Message keyboard shortcut on macOS and I have no need for the new Apple Intelligence automatic categorization features, but I do find its design to be otherwise clean and attractive. I’ll be sticking with Superhuman for the time being but if I ever got into a situation where I (rather than my company) had to pay for it then I’m pretty sure I’d bail to Apple Mail and not feel any worse for wear.

The Ready continues to use Slack for all our internal text-based communication even though I feel like I can see it deteriorating. I can’t remember a new feature they’ve introduced that actually useful. It’s getting more complex and worse every day.

We continue to use Zoom as the default video calling service at The Ready and most days I don’t really need to think about it, which is high-praise for a video calling platform. I find myself occasionally using Webex, Teams, or whatever the Google equivalent is called this week when certain clients call for it, and they all feel worse than Zoom.

Loom continues to hang around as a quick and useful way to make and share videos with each other at The Ready and with clients. It has become a mainstay in my asynchronous ways of working toolbox.

Personal text-based communication happens almost entirely in Messages.

Haven’t touched Audio Hijack in over a year but that’s more a function of “Fields of Work” being on hiatus and me not being involved in the production of “At Work with The Ready” (where we use ZenCastr).

Project Management

All my work continues to flow through Things. Emails that represent tasks get forwarded to Things, stray thoughts get captured into Things, next actions from meetings get extracted into Things — basically, anything that needs to become some sort of productive action on my part probably went through Things at some point. I periodically try replacing it with Reminders and it always feels like I’m trying to run through mud. Other than being blazing fast and having rock solid sync between my devices, the key feature that Reminders doesn’t have that Things does is the ability to “defer” a task or project until a certain date (basically, make it disappear from my system until a certain date). I use this all the time to help me focus on the stuff I can only do right now vs. the stuff I know I want to handle in the future.

The slight wrinkle to my Things-based utopia is that I have to work with other people and Things remains a resolutely single player app. The Ready uses Notion for project and knowledge management, so I have several different team-based kanban boards that I’m regularly monitoring and using. I will often manually extract tasks from Notion into Things but that sometimes gets unwieldy. If I could have my various Notion kanban boards automatically stay in sync with Things (and vice versa) I would be in heaven, but I don’t think that’s possible.

I’m no longer on any projects where we use Trello as our shared project management software.

I continue to use Fantastical with a Google Calendar backend. I’m an incredibly heavy user of my calendars because not only do I use them to keep track of upcoming appointments, I turn them into fairly accurate historical archives of what I was working on throughout the day. I experiment with the native Calendar app from time to time and I think I could probably make do if Fantastical disappeared one day. The one feature I’d miss the most, though, would be the ability to hide an event. I have a couple active calendars that are basically information radiators and once an event goes by or I have the information I need in my head I no longer want to see the information but don’t have the ability to delete it.

Reminders continues to hold a handful of recurring reminders I call Life Scaffolding as well as a shared grocery list that I collaborate on with my wife. It also is where I’ll throw any short-term reminders via Siri.

Documents, Decks, and Deliverables

Despite using Notion, The Ready still relies heavily on Google Docs, too. That’s where most of my document creation happens as I haven’t found anything where multiplayer collaboration happens smoother. We use Pitch for collaborating on most decks in real time. We use Mural for collaborating on a virtual canvas in real time (with occasional sojourns into Miro for a couple of client projects this year). I have small gripes with most of these tools but most days they feel pretty smooth and get the job done.

A lot of my early thought gathering happens in the notes app Bear. From there, that text may get shuttled over to a Google Doc or an email or a Pitch deck. I like how it looks and feels and how it handles Markdown. If I’m writing something, it’ll probably start in Bear and it may even stay in there for the duration of a project. If a piece of information is what I’d call a “Reference” it probably lives in Notes, though. For a long time it felt like I had to use Bear or Notes, but not both. I realized there are reference notes I look at pretty regularly (e.g. Weekly Review Checklist, Gift Ideas, hours the pool is open at my gym, the menu for the restaurant I order lunch from frequently) but don’t want cluttering up the space where I’m doing active work. I moved those things to Notes which allowed Bear to be an “active working space” for writing. So far, that distinction has felt pretty good.

Of course, it couldn’t be that simple, as I’m actually writing this in Ulysses. Why not Bear? Bear is for notes whereas Ulysses is where I write longer things that are destined to be articles or newsletter issues. That distinction feels useful in my brain, so I’m rolling with it.

And what about Obsidian? Obsidian is where I try to build an active “knowledge garden” with notes from the books I read, articles I write, and other pieces of knowledge building activities. I guess Notes is where I keep “life reference” material whereas Obsidian is where I keep “knowledge reference” material. It’s a quasi-Zettelkasten but if I’m being honest with myself, I’m not particularly stoked on how I’ve used/nurtured it over the last year but I’m not ready to pull the plug on it entirely.

Browsing and General Internet Things

I spent the vast majority of this year using Arc as my macOS browser. There are lots of things about it that I really enjoy (particularly the sidebar history and ability to put things in a split screen view). A couple weeks ago, though, I switched back to Safari and tried to invest a little bit of time in learning some of the “new” features that I never bothered to learn when they first came out. Web browsing feels like the number one thing to try to keep first party if at all possible. I’m not sure why, but it feels so central to the experience of using my devices I like when I’m able to use Safari across all of them. So, for now, that’s what I’m doing even though I remain a fan of Arc.

I can only go so far with Safari, though. I know it has a read later service built into it (Reading List), but as much as I try to use it I can’t make it stick for me. For 99% of this year I’ve used Matter as my read later service. I’ve been a big fan of Matter for a few years now but just recently started feeling like it’s trying to do too much. I noticed it was actually too good at surfacing other things to read that it thought I might enjoy (it was often right). I’d open the app to read an article I had saved only to be distracted by a bunch of other stuff. In the last couple weeks I re-installed my first read later love, Instapaper, and am going to try using it instead of Matter. I’m guessing its simpler design and less audacious aims might actually result in me reading more.

I’ve tried to get back into using RSS a bit more this year and have used NetNewsWire across all my devices to do so. I don’t remember why I switched from Unread.

ChatGPT (and to a lesser extent Claude and Perplexity) have grown in how much I rely on them throughout the day. I’d say I interact with ChatGPT basically every day. For awhile, I had it mapped to the Action Button on my iPhone so I could invoke it as quickly as possible, too. I’m pretty sure this whole family of apps, particularly ChatGPT, is going to continue gaining in importance for me across 2025 and beyond.

When I left Twitter a few years ago I thought I had maybe excised social media from my life permanently. With the growth of Threads and Bluesky this year, though, I’ve found myself getting pulled back into this world a little bit. I don’t post much on either one, yet, but both have a way of capturing my attention more than I’d prefer. I think Bluesky will become the place where I post more consistently in 2025 and I’ll probably continue to look at both more than I want.

Entertainment

Overcast is the only way I listen to podcasts. If it disappeared tomorrow I guess I could make the Podcasts app work, but there’s so many quality of life features built into Overcast I would miss.

Apple Music has emerged as my default music streaming service. It feels like one of those services where it has advantages over third party apps (e.g. Spotify) in how it interacts with the OS. While its algorithmic recommendations are definitely worse than Spotify there are aspects of its design I like much better. I’m also utterly uninterested in audiobooks or podcasts in Spotify and it feels like they continue to junk up their app with everything other than music.

Audible is where my audiobook listening happens. It’s fine.

I split my digital books between Apple Books (40%) and Kindle (60%). I wish I had one unified digital library but it feels like that ship sailed a long time ago.

I continue to do my sporadic personal journaling in Day One.

Logging what I play, read, and watch happens in Sofa (as well as managing the backlogs for each). I continue logging my reading in Goodreads mostly out of inertia.

Utilities

Weather nerdery continues in Carrot. Travel nerdery continues in Flighty. Training nerdery continues in TrainingPeaks and Strava. Password management is getting annoyingly split between 1Password and the new native Passwords app. Backblaze continues to silently back up my computer. Mela handles the handful of recipes I find myself referring to periodically. Rocket continues to help me put emoji everywhere and anywhere. Magnet got bumped out because macOS gained the ability to snap windows.

It’s by far my preferred relaxation activity and my favorite entertainment medium. Most mornings I spend at least thirty minutes, often more like an hour, sitting in my living room with a cup of coffee and a book. I’ll occasionally finish my day with a book, too, but that’s a bit rarer. The vast majority of the books I read are digital, with maybe a 60/40 split of those between Kindle (primarily on a Kindle Paperwhite) and Apple Books (primarily on my 11” iPad Pro or iPhone 15 Pro Max). This year was skewed heavier toward Apple Books than usual. I always have one audiobook (via Audible) going at all times so I can keep reading even when in conditions where it’s difficult or impossible to read with my eyes. I also usually have one hard copy book in the mix, too. Sometimes I just want to feel those pages between my fingers, you know?

I’m not particularly precious about choosing what to read. I do maintain a backlog in the app Sofa, but I’d say I grab my next book out of there only 50% of the time. The other 50% of the time I either have something specific in mind I want to read or I’ll let the algorithmic recommendations in the Apple Books or Kindle stores put something in front of me. I tell myself I only read one book at a time, but as I’ve already described, I typically have at least one digital book, one audiobook, and one paper book all going at the same time. To not let something linger for too long, though, I try to finish reading the whole “batch” of three before starting anything new. This year I also actually managed to abandon a couple of books I wasn’t feeling. I’ve always been an inveterate “finisher” but I’m turning a new leaf (page?), apparently.

By the numbers, 2024 is a bit down from 2023. I finished 46 books (compared to 61 in 2023) across 17,335 pages (down from 21,829 in 2023). I definitely went through stretches this year when it felt like I was just taking little sips of whatever I was reading, with increasingly long times between major gulps. I tackled a handful of particularly gnarly books (e.g., Godel, Escher, Bach, The Hermeneutics of the Subject, and The Life of the Mind to just name a few) this year which are just naturally slower to get through.

I read approximately two books of non-fiction for every book of fiction, which feels like a major skew toward fiction as compared to previous years. I actually had trouble using the fiction/non-fiction categorization because a handful of books I truly enjoyed this year seemed to straddle that line (e.g., When We Cease to Understand the World, The MANIAC, and A River Runs Through It).

My favorite fiction (or fiction-adjacent) books this year were When We Cease to Understand the World, American Gods, and Children of Time.

My non-fiction reading seemed to hit a few key themes:

1. Personal development, self-exploration, and the philosophy of living well (On Becoming a Person, The Hermeneutics of the Subject, The Life of the Mind)

2. Systems-oriented perspective on interconnected social, economic, and ecological systems (Systems Thinking for Social Change, Complexity, The Regenerative Business)

3. History, power, resilience, and societal structures (Gulag, Kissinger, History of the Peloponnesian War)

4. Epistemology and the boundaries of knowledge and consciousness (Godel, Escher, Bach, I Am a Strange Loop, Knowing What We Know, How to Live: A Life of Montaigne)

5. Contemporary sociotechnical and cultural phenomena (Filterworld, Number Go Up)

I’m most proud of myself for having finished Gulag, Godel, Escher, Bach, Hermeneutics of the Subject, The Peloponnesian War, and The Life of the Mind. The book I’m most likely to re-read at some point is probably Slow Productivity and Liberalism as a Way of Life. I was most positively surprised by The Goblin Emperor.

I read a handful of authors for the first time this year, and I’m excited to read more from them: Norman Maclean, Anne Applebaum, Adrian Tchaikovsky, Katherine Addison, and Ted Chiang. A handful of old stalwarts showed up as well: Cal Newport, George Saunders, James S.A. Corey, and Siddhartha Mukherjee.

Reading in 2025

I’m committed to keeping my reading practice as simple and robust as possible. I know I read a lot, and I’m okay with that. I don’t really feel the need to read more (even though this was a “down” year compared to 2023). I think I’d continue to benefit from reading more fiction than I currently do, and I’d like to see myself dig into more classic literature. If there’s one thing I’d like to do differently in 2025, it might just be trying to be a bit more deliberate about continuing to explore specific lines of inquiry. I started that a bit this year with my Foucault, Hodot, and Montaigne reading all falling around a similar theme. I think there’s more of that to be done, particularly around topics related to AI and consciousness (and really any of the themes that showed up in 2024).

Aside from books, which make up 95% of my reading time, I do try to consume some magazines and newsletters. I used Matter as my read later service for the vast majority of the year. I saved tons of articles into it and read only a tiny percentage of them. I use NetNewsWire as my RSS reader, and I’m looking forward to leaning much more heavily on it in 2025 as I try to limit my exposure to algorithmic recommendations as much as possible. I get physical copies of The Economist, Harvard Business Review, Nautilus and Palladium. I continue to pay for and enjoy Stratechery. I’ll continue to tweak what non-book related writing I pay for in 2025 as I’m committed to directly supporting more of the authors and sources I enjoy.

You can follow me on Goodreads and see my entire 2024 reading list here.

All glory is in the new. Every January there are countless words written about what people are going to do differently. What about everything you deliberately (or not so deliberately) decide to keep the same? I think consistency and looking at what has remained constant over the past year can be even more enlightening.

Software & Hardware

Like most years, I went through a multi-month phase where I used almost all default apps across each category where there is one. That meant using Apple's Podcasts, Notes, Music, Mail, Calendar, Safari, Keychain, Pages, and Reminders apps as my productivity stack for well over a month (probably closer to two). And like every other time I’ve done this experiment, I ultimately ended back with a bunch of my tried and true third party apps that are a better fit for how I like to work and what I want out of my tools.

Specifically, that meant Fantastical, Things, Ulysses, Bear, Spotify, Superhuman, 1Password, CARROT Weather, Day One and Overcast were all frequently and (mostly) happily used just like they have been for many years at this point. Some of these have been in my toolbox over a decade and are so deeply embedded in my muscle memory they feel like a natural extension of my very being.

Other mainstays include Magnet, Rocket Emoji, Audio Hijack, Backblaze, Unread, Flighty, Due, Mela, Strava, and TrainingPeaks. All have been in use for many years and do their jobs well.

On the work front, not much has changed in The Ready’s productivity stack as I still find myself using Slack, Google Docs, Zoom, Trello, Loom, Notion, Mural/Miro, and Pitch pretty continuously to get my day job done.

The centerpiece of my computing hardware remains unchanged, a M1 MacBook Air (2020) that I have plugged into a 27” HP monitor (2019) and an old Magic Mouse (unknown) + Magic Keyboard with Touch ID (2022) combo. My desk headphones are AirPods Max (2020) and my walking around headphones continue to be AirPods Pro (2019, re-purchased in 2023). My desk remains a Fully Jarvis sit/stand desk (2015) and my chair is a well-loved Herman Miller Aeron (2015). My two original full-size HomePods (2018) are still chugging away and their little brothers, a pair of HomePod Minis (2020) are still around and doing their thing.

My Nintendo Switch (2017) continues to be the least portable portable gaming system I’ve owned (I swear, my hands must be anti-Switch shaped). My TV remains some random TCL (2018).

PowerBeats headphones (2021) are my go-to training headphones. My Garmin Forerunner watch (2021) and Edge bicycle head unit (2021) both continue doing their respective jobs in the triathlon training realm. My mystery year Trek Madone Craigslist bike (bought used in 2021) continues to be my only training and racing bike and my Wahoo Kickr Snap (2022) continues to let me avoid riding outside in the winter.

In the kitchen, my KitchenAid stand mixer (2020) is a tank and used at least weekly to make bread, the Arc water carbonator (2020) gets a continuous workout, and my Fellow water kettle (2020) and grinder (2022) are the mainstays of my morning coffee routine.

Life & Work

I continue training for triathlons, as I have since the summer of 2021. 2023 marked my second full year working with a coach and consistently training throughout the year. I completed two races, one of which was the half-Ironman distance I’ve had my eye on since I originally started training. I cycled 2,236 miles (down from 2,542 miles in 2022), ran 528 miles (up from 472 miles), and swam 95,350 yards (down from 97,558 yards) across the whole year of racing and training. For the second year in a row I participated in a training camp on the Eastern Shore of Maryland with my coach and some of the other athletes he coaches. This remains almost the only time I train with other people. 99% of my training time is spent alone.

I still read quite a bit. In 2023 I finished 61 books and 21,751 pages (up from 44 books and 18,159 pages in 2022 but down from 22,123 pages in 2021). I re-read three books; How to Do Nothing by Jenny O’Dell, Ten Arguments for Deleting Your Social Media Accounts Right Now by Jaron Lanier, and Bird by Bird by Anne Lamott.

I continue to watch only a little bit of TV (eight seasons spread across eight shows) and movies (13, four of which were re-watches). While I don’t watch much scripted TV, I do continue to watch most Detroit Red Wings games on TV. In a given season I’ll probably miss fewer than 10 games (out of 82).

Sampson Boat Co, That Triathlon Life, and Lionel Sanders remain the handful of YouTube channels I consistently watch.

Most of the podcasts in my roster have remained unchanged, with the following being shows I tend to listen to every episode of and have been in rotation for many years (some, over a decade): Cortex, 32 Thoughts, Accidental Tech Podcast, AppStories, Connected, Dithering, My Brother, My Brother, and Me, Philosophize This!, Reconcilable Differences, Robot or Not?, Roderick on the Line, Sharp China with Bill Bishop, Sharp Tech with Ben Thompson, Stratechery, That Triathlon Life Podcast, Under the Radar, and Upgrade.

I continue to aim to go to bed around 10:00 PM and wake up around 6:00 AM on most days. My morning routine has remained unchanged with coffee (AeroPress or pour over) and miscellaneous mess-around-on-my-phone time until 6:30, reading a book until 7:00, making and eating breakfast until 7:30, and generally starting my work day around 7:30. I’ve fully embraced my early lunch tendency and generally eat lunch between 11 and 11:30 most days. I try to finish work by 4:00 PM so I can workout before it gets too late and all motivation leaves my body. Sometimes I’ll do an early afternoon workout and work until 6:00 PM instead.

I continue to try to be the last person on the airplane (unless I can be one of the first) and I continue to view the ability to travel for my work as a privilege.

I continue to mostly embrace minimalism as an aesthetic, principle, and quasi-hobby.

I continue to make dinner most nights (while Emily is in charge of clean up). There’s probably about 10 dishes I regularly make for us, but I haven’t learned a new staple to include in the rotation in a while. Our default dinner continues to be “dope salads” (lettuce, miscellaneous veggies, roasted sweet potato, and some sort of protein, usually roasted chicken). My default breakfast is oatmeal with blueberries and too much brown sugar and butter to really consider it particularly healthy. I continue to lean on DoorDash more than I should when I’m feeling unmotivated to cook.

I continue to be the family Chief Logistics Officer. I’m in charge of groceries, other household supplies, general maintenance, and all travel logistics. I enjoy this role.

I continue to write sporadically, at best, with only three issues of The Deliberate published in 2023 and only one article published on SamSpurlin.com. My brother, Max, and I continue to record our podcast, Fields of Work, with seven episodes published in 2023.

I still work at The Ready and split my time between various internal initiatives and leading client projects. I continue to think that what we’re trying to do is exciting and that I’m well-suited to do the type of work I do. I continue to feel grateful (almost) every day about this.

I’m still married (2021) to my best friend and the best person I know, Emily. We still live in Arlington, Virginia in the same apartment we moved into together in December 2017. We continue to take a summer vacation on Cape Cod every year so we can visit Emily’s parents. We get back to Michigan to visit my family at least once a year, too.

I continue to think about the intersection of attention, personal development, organization design, and philosophy a whole lot. I continue to struggle with walking the balance between wanting to see myself grow and being okay with who and how I am. I think I’m getting better at it.

Want more? Sign up for The Deliberate, my continuously intermittent newsletter.

That being said, I do think there's something to be said for intentionality. I think themes are a nice way to put some very light guardrails around some intentions without turning them into a yearlong goal-slog. Even better than guardrails, articulating a theme is a way to create a useful attentional lens that you can use in surprising ways to notice what's going on around you in new ways.

I've used theme(s) in the past, but I've never tried to use them in explicit conjunction with my other favorite method -- the personal experiment. It seems like an obvious connection, though, right? Set a theme or two that basically gives a useful directional heading for the year and then use relatively short (one to three week) personal experiments to explore within those themes. So, that's what I'm going to try this year: set a couple broad themes that describe the general areas I feel like I need to explore this year and commit to running as many experiments that investigate, challenge, and push against those themes as I can usefully metabolize over the next twelve months.

In no particular order, here are the three general themes I want to use to bring some structure to my personal experimentation in 2023.

Focusing

As David Allen says, the better you get the better you'd better get. I'm seven and a half years into an intense consulting career. As I've gotten better at my job I've found myself in progressively more complex environments that seem to regularly come with higher-stakes moments than ever before. I love it, but it requires that I keep getting better at what I do. If I stay stagnant I will get overwhelmed. One way to stay stagnant is to constantly feel like I'm being pulled in many directions simultaneously and not actually developing deeper expertise in anything.

One of the things I've learned about myself is that because I have such well-considered and robust systems for being productive, I have a tendency to take on way too much. Because my capacity for work is high, it's very easy for me to fill that capacity with relatively low-impact busywork that fills the hours but doesn't necessarily create the outcomes I want to see. It's time for me to really start figuring out how to eliminate those attractive nuisances and focus on the highest impact stuff that only I can do.

Possible Areas to Experiment

• What kinds of caps/rules/limits can I put in my days/weeks that will force me to get better rather than just working harder?

• What commitments feel inviolable but are actually distractions? Do I have what it takes to step away from them?

• How do I better match the type of work to the energy it needs? How do I build the most important work I have to do into my most naturally energetic periods of time?

• What does it look like to take my existing hobbies and interests deeper?

• How can you be a curious person and also focused?

• What does it look like to always take the most direct moves from where I am to where I want to be?

Relating

I often focus on myself too much. I can take my interest in personal development too far and in doing so become insular. I often lose sight of the fact that I'm part of a network of relationships that are incredibly important to me. I'm a new husband as of this year. I have four younger brothers who are my best friends but also live many states away. As The Ready grows I have friends/colleagues who I used to work with side-by-side every day but now only seem to see or talk to a couple times a year. I have friends from graduate school who I only periodically exchange text messages with. I don't need to sustain every friendship forever and I don't need every friendship to be deeply intimate. But I wonder if I'd feel better about myself and my life if I spend more time and energy on my relationships in 2023?

Possible Areas to Experiment

• If Emily and I are going to stay in the Washington D.C. area long-term, as it looks like we might, are we building relationships with people and building community here?

• What's the right cadence and format for keeping my most important relationships healthy?

• How can I be a better friend? Brother? Son? Husband?

• I've neglected my social life pretty consistently for most of my life. Is that something I want to do? Am I missing something by being aggressively reluctant to "do things"?

Creating

A solid 75% of my journal entries from 2022 were me lamenting that I wasn't writing enough and how terrible that made me feel. I know I only tend to feel my best when I'm consistently writing. I used to think this was evidence of some kind of latent narcissism that was looking for a way to express itself. I worried that my writing was a way to demonstrate my intelligence to people I admired. Writing as head-pat-mechanism, basically. I've recently learned I really don't think it's about that for me (although I won't turn down a head-pat from someone I admire). It's the fact that writing consistently means I'm thinking consistently. And, on the flip side, if I'm not writing it means I'm not actually thinking very deeply about much of anything. I want to be a deep thinker. I want to wrestle with big questions and make sense of the world around me. I can only do that if I'm regularly prioritizing the time to make my thinking visible (even if only to myself).

When I don't write enough I feel like I'm wearing a damp sweater that I can't take off. It's profoundly uncomfortable and all encompassing. Every subtle movement is a reminder that this sucks. Sometimes, it even seems like I don't have the power to remove it. Which is stupid, right? I can just take it off. I could just write more. That's it. Simple. It's time to hang the Damp Sweater of Non-Creation in the closet and never look at it again.

Possible Areas to Experiment

• How much do I need to write in a given day, week, month to feel like I did enough? Is it time-based? Page-based? Publication-based? Something else?

• How much can I write in a week?

• What types of writing should I experiment with more?

• What would it look like to make a concerted effort to actually participate in social media more (rather than primarily as a consumer)?

• How can I lean into working-in-public while still having the patience and discipline to spend the right amount of time to create something really great?

• Can I build some sort of momentum around a body of work related to The Deliberate?

My intention is to use my Deliberate Pattern Library as the ongoing record of what experiments I'm doing throughout the year and what I'm learning from them.

I imagine I'll write about most of the experiments as I do them in The Deliberate, too. I'm not necessarily going to hold myself to always be running an experiment (it can be nice to take a break) but I imagine more often than not I'll be doing something toward one of these themes (even if it's quite small or simple). I'm also not saying that I won't do an experiment that doesn't align with one of these themes if it feels useful or interesting.

Ultimately, I'm hoping the commitment to both themes and a rhythm of experimentation will help me uncover the things that I'm not even thinking about right now. These three themes of Focusing, Relating, and Creating have interesting overlaps, tensions, and implications that I can't see from my vantage point today. Only by digging into them through experimentation will I start to uncover what they have in store for me.

Ten years ago I wrote a yearly review that I cheekily called State of the Sam. I was going into the last year of a positive psychology master's program at Claremont Graduate University and was a couple weeks away from hearing that I was accepted into the PhD program (which I would ultimately drop out of several years later -- but that's a different story for another time). I was 25 years old. I had been dating a girl for about a year and a half. We had just gone camping at Joshua Tree National Park. She visited me in Prague when I lived there over the summer. Now, we're married. 

I wrote about the software I liked, particularly Things and Fantastical. Things and Fantastical are still the backbone of my daily productivity. All that is to say, ten years is a long time, things change, and even more things, maybe surprisingly, stay the same.

It’s fun to look back and see how a year went and it’s even more fun to look back 10 years later and see what felt like it was worth mentioning. So, to give 2032 Sam something to read, let’s do it again: another State of the Sam.

The Year of Work

I'm tempted to punt on this first section by simply pointing you to one of the very few articles I wrote this year that happened to be a long retrospective about my career. I mean, it's pretty good so if you're extremely curious about how I'm thinking about my work as an organization design consultant at The Ready (my employer for the last seven and a half years), I recommend you check it out.

As far as 2022 goes, though, I suppose I could dive into the weeds a bit more. The first part of the year I was 100% supported by The Ready to co-lead our DAO and web3 exploration. The full explanation of that work is probably outside the purview of this article (and this article I wrote from late 2021 is a pretty good summation of where my head was at in early 2022). I got to spend a bunch of time learning a completely new area, building relationships with people who work in that space, and generally trying to figure out how to bring The Ready's work to a community and movement that could absolutely use our assistance, if we could just figure out how to package it in a way that resonated with them. It's hard to say how successful we've been because this work happened to coincide with a particularly nasty downturn in the crypto markets.

Roughly halfway through the year The Ready decided we could keep that work alive while shifting some of our time and attention to other (revenue generating) projects. That meant that for the first time in a long time I was going to be sinking my teeth into another (hopefully) long-term transformation project with a more traditional client. I had wrapped up my last major engagement early in 2021 and then went on my 4-month sabbatical only to immediately jump into our DAO work when I returned. I was actually really excited to get back into some work that felt like it was more squarely in my wheelhouse. What started as a project designed to take half of my time with a partner turned into a full-time project that I worked on largely by myself for the last four months of the year. I really enjoy the client and the work we are doing together. I vacillate between whether I like working as almost a free agent within The Ready or whether I miss having a teammate to help shoulder the load and push me to be better. It really depends on the day.

I think I'm doing very good work with the client and they're happy (we just extended our arrangement for at least the first three months of 2023). Without going into too much detail, one of the things I'm helping them with has the potential to be a repeatable and generalizable program/product that I think The Ready could scale. I hope to validate this initial pilot version with this client in the first quarter of 2023 and hopefully have enough data to bring it back to The Ready as something we can try to sell elsewhere.

I still feel great about The Ready and I'm proud of what we're doing and how we're doing it. We're growing in headcount, impact, and influence while sticking to our principles. I really can't imagine a better place to let me bring the best version of myself to bear on gnarly problems. I'm grateful for the flexibility that allowed me to take time off for my wedding and honeymoon (more about that below!) in addition to a normal summer vacation. My year did feel a little bit fractured with extremely large and disruptive (in the absolutely most positive sense) events so I'm looking forward to really dialing myself back in as a senior member of the The Ready who can do a lot to help improve the organization for everyone else and as a consultant who is constantly trying to elevate my own practice.

We held three full company retreats last year; one was virtual (the tail end of the Omicron outbreak was happening), one was in New York City (it was kind of surreal to remember that I used to live there), and the last one was in Miami (good call for a late fall retreat location, right?). I did one quick jaunt up to Toronto to meet with my DAO Circle co-steward, Tanisi, for a full-day in-person strategy meeting. I attended a conference called ETHDenver in, well, you can figure it out. And I had one trip to Boston to facilitate an in-person workshop for a client. A relatively light year of work travel, all things considered.

My hardware setup has remained almost completely unchanged. I'm still using a stock M1 MacBook Air as my only computer, a 27" HP external monitor, a Logitech webcam, AirPods Max, a Blue Yeti mic on a boom arm, a Fully Jarvis sit/stand desk, a Herman Miller Aeron chair, and an iPhone 12 Pro Max. The only new piece of hardware was upgrading my old Apple Wireless keyboard to a new Apple Wireless keyboard with a built-in TouchID sensor. Wanted to live that fingerprint-as-password lifestyle, you know?

The Year of Life, Travel, and Relationships

I got married this year! After a decade of being a couple and roughly four years of living together, Emily and I tied the knot in Naples, Florida at an absolutely perfect event hosted by her parents. Really, I'm not sure it could have gone smoother. Being surrounded by friends and family for a couple days of pure celebration is one of those things I have a feeling you never really forget.

We decided to not immediately leave for a honeymoon, as various uninteresting logistics considerations made it make more sense for us to go at the end of September. Which we did with a Mediterranean cruise that started in Rome and hit Naples (the Italian one), Barcelona, Mallorca, Marseilles, Florence/Pisa, and back to Rome. We capped the trip with a flight back to Barcelona so we could attend Emily's brother's wedding. All-in-all, a truly once-in-a-lifetime travel experience and well worth the several month wait.

Another highlight from the year was doing our third annual Spurlin Brothers' Weekend. Every year my four younger brothers and I try to find a location that is a.) interesting(ish) and b.) in a relatively central location for all of us. Previous locations have been a cabin in Michigan along Lake Huron, an Airbnb in the woods in Pennsylvania, and this time around it was an Airbnb on a farm just south of Columbus. This has quickly become one of my favorite traditions that I look forward to every fall. Since we are all super nerds, it's basically a 2-day marathon of board games and frozen pizza.

Other trips included a pre-wedding trip to Florida to do some preparations (I had a near run-in with a ~10 foot alligator), a trip to Cape Cod to visit family and have a vacation, and a trip to Michigan to have a second wedding celebration in my parents’ backyard for family and friends who couldn't make it to Florida. Closer to home, I did a several day triathlon training camp on the eastern shore in Maryland, a race a couple hours drive south of us, and two races in Williamsburg, Virginia.

New Hobby Alert: Triathlon

After yet another concussion during beer league in 2020 I decided I needed a less dangerous athletic hobby. After properly mourning the end of my hockey "career," I decided to give triathlon a shot.

I technically started my triathlon journey in late 2021 by hiring a coach and getting started on a regular training schedule, but 2022 was my first full calendar year of consistent training and racing. I went into the year with the goal of finishing three races: a sprint distance in April (750 meter swim/12 mile bike ride/3.1 mile run), an Olympic distance in June (1,500 meters/24 miles/6.2 miles), and a half-Ironman (1,900 meters/56 miles/13.1 miles) in September. I did end up doing the three races, but they were slightly modified after I developed tendinitis injury in my right foot after the second race. Instead of rushing myself back from injury too quickly, I decided to step my planned half-Ironman race down to the Olympic distance to allow myself the proper time to heal without the looming pressure of a very long race on the horizon. That was a good and smart move that I'm not sure Sam from ten years ago would've made. I've been telling myself that I'm in no rush to do anything overly specific in triathlon. I want this to be something I can and want to do for the next twenty years, not something I burn out doing after two.

This warrants a longer article at some point, but I've loved my experience training for and doing triathlons. I've brought a level of consistency to this endeavor that I wasn't sure I was possible of. It isn't about ever becoming "good" at any of the three disciplines. I will never be fast enough to compete for a podium in my age group. I've always said that my only goal with all my races, at least so far, is to "finish with dignity." So far, I've been able to do that.

According to TrainingPeaks, the software I use with my coach to plan and record my workouts, I've completed the following in 2022 (with one week of training yet to do): 2,491 miles of cycling, 459 miles of running, 98,900 yards of swimming. More importantly, I've truly enjoyed the vast majority of these miles and yards. It has been incredibly gratifying to see myself go from not being able to run more than a mile or two without my shins hurting to running for well over an hour without a problem. To go from gasping for air after 50 yards in the pool, to being able to swim nonstop more or less indefinitely. To go from considering a 20 mile ride as particularly noteworthy to finishing my first ever 100 mile bike ride.

If you're curious to follow along with my training, I use Strava to track my training pretty consistently and you can follow me there.

The Year of Creative Output

My creative output was spread across a few different projects. My brother Max and I continued our podcast called Fields of Work all about our very different experiences of work (he's a small scale organic farmer and I am very much not). We recorded nine episodes, which is probably a few fewer than we would have liked to have recorded. The show now has 63 episodes in total and we've been doing it since the summer of 2019. We're both very happy to continue our very non-professional approach to it because the last thing either of us wants to do is suck all the fun out of what is really just two brothers having a phone call and catching up on each others' lives every so often.

My newsletter, The Deliberate, continues, at least in theory, as I only managed to publish it three times this year.

I published seven articles (not including this one) on my website, SamSpurlin.com or on The Ready's Medium publication this year. The only one that felt like a meaningful attempt at pushing forward my independent thinking and writing around deliberate work was the one I published in March, "Stop trying to change your habits and start playing with Deliberate Patterns instead." This was my first attempt at trying out the new nomenclature I had been developing -- "deliberate patterns." Another article I published this year that I'm kind of proud of because it felt real and personally therapeutic was also from March, "I never properly mourned the end of my hockey career." The remaining articles were a look at bringing the idea of operating systems to DAOs, a race report from my first ever triathlon, an experiment in going "monk mode" to work on something difficult, a seven-year career retrospective, and a look back at the software I used in 2022.

Related to my writing about The Deliberate, I finally made progress on some of the ideas that I tried to pull into a book proposal in 2021 before realizing that I needed to go back to the drawing board with some of the basic ideas. It has manifested as a public Notion board that I call the Deliberate Pattern Library where I've started gathering examples of these deliberate patterns -- little recipes that I, and others, can either experiment with or try to internalize. It's still very much a work in progress but it felt good to finally start chipping away at this amorphous intention that has been floating around in my head for the better part of a decade.

Finally, I had the opportunity to appear on a couple podcasts this year. First, I was on an episode of Bounty Hunter (now called Quorum) talking about the work The Ready is doing with DAOs. Second, I was on a very long episode of The Clique Podcast talking about organization design and DAOs. This one happens to be available as a three-part YouTube series, too.

Ultimately, I'm deeply unsatisfied with how much I created this year. I wanted to do more writing for The Ready. I wanted to do more writing for The Deliberate and SamSpurlin.com. Hell, I even wanted to do more personal journaling just for myself. I need to figure out how to make this be the last time I ever write a yearly review where I lament the fact that I feel like I'm leaving my creative potential on the table.

The Year of Entertainment

Books

I made the intention to read more fiction in 2022 than I had in previous years. There have been years in the recent past where I've read 50-60 books and fewer than 10 of them would be fiction. That was something that needed to stop and I'm happy to say I read more fiction in 2022 than I ever have before. I completed 18 pieces of fiction including a couple of absolute chonkers like the Iliad and Rhythm of War. A few of my favorites: the “Remembrance of Earth’s Past” series by Liu Cixin (blew my mind), the “Millennium” series by Stieg Larsson (maybe the most addictive books I've ever read), and the two-part “Daemon” series by Daniel Suarez (incredibly compelling). I feel like I've seriously tapped back into my love of science fiction and fantasy over the past year and I intend to go much further down that rabbit hole in 2023.

My big nonfiction win for the year was finding the author John McPhee. Something about the way this guy writes is utterly mesmerizing. I found his 716 page book about geology hard to put down. If a dude can write in a compelling way about rocks then he's obviously a master of his craft. I read a couple other books of his, including one about his writing process (Draft No. 4) and now I can't wait to work my way through his entire bibliography.

The Timeless Way of Building by Christopher Alexander was another important book for me this year, as it gave me the "pattern language" idea and terminology that I've been using in my The Deliberate thinking and writing.

Overall, it looks like I'll clock in at 44 books read this year. This is quite down from the last few years (58 in 2021, 53 in 2020, and 60 in 2019). In terms of pages, I'm at just over 18,000. That's about 3,000 pages fewer than 2021, 400 more pages than 2019, and about 1,000 pages fewer than 2019. That brings things more in line with what I'd expect a year of reading that included multiple 700+ page books to look like.

Reading, as you might expect from what I just shared above, is the primary way I spend my time when I'm not working. Meaning, the next few sections are going to be pretty short.

TV

My TV year has mostly been consumed by an ongoing re-watch of It's Always Sunny in Philadelphia that I've been doing with my wife, Emily. We don't watch very much TV (maybe 2-3 episodes of a single show per week) so it has been taking us a while to work our way through it (we're on season 13 so we're almost done). Other shows we tucked into this year include the second season of The Witcher (feels like the wheels are starting to fall off...), Severance (so good), season 2 of I Think You Should Leave with Tim Robinson (Tim Robinson quotes comprise the vast majority of our inside jokes as a couple), and Prehistoric Planet (surprisingly good).

As far as solo shows go, I finished the final season of The Expanse (pretty good), The Queen's Gambit (pretty good), and House of the Dragon (pretty good). I've delved into YouTube a little bit more than in previous years and have really enjoyed the Sampson Boat Co. project channel (restoring a wooden sailing yacht by hand), a couple of triathlon-related channels (That Triathlon Life and Lionel Sanders) and a chess-related channel (Gotham Chess).

Movies

I watched a grand total of six movies this year. Jurrasic World Dominion because I'm a sucker for nostalgia and dinosaurs and Elvis were the only two I saw in the theater. Rewatching The Matrix for the first time since it came out was like watching it for the first time (thanks terrible memory!). Encanto was fine and Hunt for the Wilderpeople was maybe my favorite movie of the year. Nope was weird and good.

Games

I went incredibly long periods of time this year where I barely touched one of my favorite hobbies, video games. The games I did finally sink some time into, though, were very much worth it. Two in particular, Control and Hades, are among the best games I've ever played. Starcraft 2, my old mainstay, was around for most of the first couple months of the year but fell away hard after about May. Slay the Spire and Vampire Survivors have been great mobile games that are actually just great games, period.

The game that really signifies 2022 for me, though, is chess. Specifically the Chess.com app and the constant ongoing games I have with a couple of my colleagues. I'm still terrible at it, but I've been making some progress in actually learning some of the basics that might help me not get absolutely stomped every single game.

Podcasts

Podcasts remain the primary audio entertainment that kept me company (probably too much company, to be honest) throughout 2022. Most of the roster has remained unchanged for years at this point. I'm the type of person who doesn't really browse through various podcasts. I have a handful that I listen to almost every single episode of and a few where I'll pick and choose episodes based on topic. For the curious, the former group consists of: 32 Thoughts, Accidental Tech Podcast, The Adventure Zone, Connected, Cortex, Dithering, Exponent, Fields of Work (yes, I listen to my own podcast), The Always Sunny Podcast, My Brother, My Brother and Me, Reconcilable Differences, Robot or Not?, Roderick on the Line, Sharp China with Bill Bishop, Sharp Tech with Ben Thompson, Stratechery, That Triathlon Life, Under the Radar, Up First, Upgrade, and The Vergecast.

The newcomers in 2022 are the two new "Sharp" podcasts that are part of the Stratechery bundle. Both have been very good right from the beginning. Philosophize This! has been the one podcast where I've been working through the 150+ episode back catalog. The only other notable development in my podcast listening is that the back catalog of You Look Nice Today has somehow become my "go to sleep podcast" whenever I'm going to sleep by myself. Weird, I know.

Music

Any year where a new Coheed and Cambria album comes out is a good music year in my book.

Miscellaneous Good Things

• Getting all my consumable household supplies on an automatic schedule with Amazon has been rad. Have done the same with the vast majority of my groceries, too. I'm always looking for ways to automate the things I have to do on a recurring basis and both of these have been big in 2022.

• Combining finances with Emily after our wedding was smoother and simpler than I thought it would be. A shared checking account, a shared savings account, a couple shared investment accounts, and a couple individual investment accounts (through our respective employers). We use the same shared credit card (points, yo!) for all our shared expenses and pay it from our shared checking account. Don't think it really gets much simpler than that.

• I mislaid my wedding ring almost immediately after getting married. I now have a bag of silicone wedding bands that I keep in a drawer next to my bed. I initially felt terrible but now I feel totally fine about it. It’s more comfortable, looks fine,  and I don’t have to worry about any inadvertent grievous injuries caused by getting my ring stuck on something.

• I experimented with letting go of specifically tracking or even trying to do my Anchor Habits for a large portion of 2022. My Anchor Habits were daily intentions to Move, Sit, Read, and Write. I was rarely hitting all four of them in a day and realized the low-level bad feelings that created in me weren't particularly helpful or wholesome. I let go of the intention and so far haven't felt the need to bring them back. Most days I Move and Read just fine. Some days I Write. I haven't Sat (meditated) consistently in months. Right now, I'm okay with that.

• I experimented with getting on a very consistent sleep schedule (bed around 10, awake via alarm at 6). I also experimented with going to bed as consistently as possible (still around 10) but waking naturally (usually between 6:30 and 7:30). I went back and forth on what is better for me and have decided, for now, that I'd rather have the predictability of the same wake time every morning even if that means I'm slightly underslept. I realized I could get the benefit of both, though, if I let myself go to bed a little bit earlier if I was feeling sleepy, so that's what I've been doing.

• Writing up my internalized Deliberate Patterns has been fun. There are too many to name here, so check out the Deliberate Pattern Library if you're curious.

Making Sense of the Year

It's a cliche for a reason, but every year feels like it flies by faster than the last one. I kind of can't believe I'm sitting here a couple days before Christmas and writing a recap for a year I could've sworn was just getting started. It makes me realize that my obsession with learning how to become more deliberate, and sharing what I learn along the way, is definitely worth the effort. When I was younger I could let years pass without being particularly deliberate and still feel like time was basically dripping by. Those days are over. Time has become a torrent and I'm lucky if I don't get swept away by it. Being deliberate is the only way for me to get my bearings, anchor myself, and actually have a shot at navigating my life in a way that feels aligned with who I am and who I want to be.

While I'm in awe that the year is over, it's obvious that it was a monumental one for me. Getting married to Emily, celebrating with friends and family in Florida and Michigan, going on a honeymoon to Europe, doing meaningful work at a cool company, spending a few days in a rented house with my four younger brothers, developing a new hobby and fitness routine that has pushed me to new levels of achievement and health -- the highlights are almost too numerous to list. For that, I'm grateful.

My creative output, or lack thereof, is the main blemish on what I would consider a very good year. There is a part of me that I have not honored to the level that it deserves. It wants to be creating, specifically writing, much more than it has been. It's easy to tamp down that voice when work is busy and when I can tell myself that even though I'm not doing much writing publicly, I'm doing a bunch of writing in the course of my day-to-day work. Or that the conditions are never quite right ("I'm too tired, I have too much to do, I don't have any ideas that feel worth writing about, etc. etc.").

That voice is getting harder and harder to ignore. Even if I could ignore it, I don't want to.

This article originally appeared on SamSpurlin.com, which is where I publish all my new writing first. Add it to your RSS reader and/or subscribe to The Deliberate. The Deliberate is a periodic newsletter I publish any time I've written something new on my website. Subscribing to it is probably the best way to be aware of when I publish something new. Or, if you're a masochist like me, you can follow me on Twitter.

As a knowledge worker, the software I use determines a lot of my experience at work. I seek software that either gets so out of my way I never think about it (like a reliable appliance) or even better, gets out of my way while somehow being simultaneously delightful to use (like a reliable appliance with knobs that feel amazing). I take the task of selecting, learning how to operate, and evaluating the software I use to live my life and do my work seriously. That doesn't necessarily mean I'm always looking for something new (which you'll see as most of the list that I'm about to share below has remained unchanged for years), but that I'm always reflecting on my workflows, tools, needs, and figuring out how I can most directly and simply take aim at what I'm actually trying to do with as little distraction as possible. I want tools that will help me narrow the distance between my intention and my impact.

What follows below is a list of most of the software I use and a few words about why I use it. It's a mix of stuff that I choose for myself and stuff that I have to use for reasons other than, "I like it," (like because it's what my company has decided we're going to use).

My hope is that you a.) find a tool that better suits your needs or, more importantly, b.) are simply inspired to bring a little bit more deliberate attention to your existing set of tools.

See previous versions of my yearly software recaps here:

• 2021
• 2019
• 2018
• 2017
• 2012

Safari (macOS/iOS)

Browsing
Safari has been my primary browser on mobile and desktop for basically as long as I can remember. It’s mostly rock solid (except when it isn’t) so I only find myself opening Chrome when I’ve hit some sort of web app that won’t work (or won’t work well) with Safari. I also keep Brave around for some of my crypto-related activities which I’ve been doing more of over the past year and a half. There are definitely things getting added to Safari that I don’t really use (hello, tab groups) but as long as any important functionality doesn’t break or regress, I don’t see myself moving away from it any time soon.

Spotify (macOS/iOS)

Music Streaming
I’ll periodically peek over the fence toward Apple Music for a week or two, but I’ve come back to Spotify every single time and felt a sense of relief to do so. I used to ding Spotify for having a subpar design as compared to Apple Music, but I don’t feel that way any more. I’m not sure if I’ve just gotten used to how Spotify works and looks, if Apple Music has failed to evolve, or maybe both — but I actually prefer Spotify’s design language and UX nowadays. My Discover Weekly playlist continues to be a banger every Monday morning. I don’t love that they keep trying to push podcasts and audiobooks in front of my face. If that ramps up in the coming years I may have to give Apple Music another chance.

Overcast (iOS)

Podcasts
Overcast continues to be the only podcast player I use and it continues to be great. I don’t care about my podcast player surfacing new podcasts — I just want it to be amazing at playing the ones I choose to subscribe to. I also enjoy using it because I like listening to Marco Arment talk about developing it on Accidental Tech Podcast and Under the Radar. It’s always interesting to see the changes he has been talking about roll into the app and I like supporting an indie developer.

Superhuman (macOS/iOS)

Email
I’m fortunate to not receive a ton of email, so my choice of email software is not as consequential as it might be for most. That being said, I still want to interact with my email as fluidly and sparingly as possible while still using a native (i.e. not browser window) app. I like being able to use keyboard shortcuts without modifier keys (like Gmail in the browser) to handle my email and since my work is willing to pay for my Superhuman account, I’ll happily use it. If I had to drop my own money, I’d probably just go back to Airmail or the default Apple Mail app.

Fantastical (macOS/iOS)

Calendar
I feel similarly to Fantastical as I do about Things. It has an incredibly high level of polish and is just generally pleasant to use. I haven’t really leaned into any of their new scheduling features (since I’m still using Calendly when I need someone to find some time with me). So, like with Safari, I’m kind of stuck in the past in the sense that I don’t care about or use many of the newer features that have been added. I mentioned Cron in the 2021 State of the Tools article but haven’t felt the desire to explore that tool any more.

Bear (macOS/iOS)

Ephemeral Note Taking
In 2022 I continued to use Bear as the “default writing space” on my computer. Any time I needed to quickly begin writing I opened Bear and just got to typing. I figure out what to do with it (save it somewhere more permanent, send an email, send a Slack message, etc.) afterward. You’ll notice I’m using the past tense in those previous sentences because in the past couple weeks I have retired Bear in favor of Obsidian. I’ve built a fairly robust note-taking system in Obsidian and it felt increasingly foolish to split out ad hoc note taking into Bear since theoretically I’d love to have that content accessible to my note taking system. So, it’s still early days of seeing whether Obsidian can step into the role Bear played but I’m optimistic it can do the job. Which, honestly, is kind of sad because I think Bear is a great app. You should use it if you’re looking for a beautiful place to take notes.

Ulysses (macOS/iOS)

Longform Writing
Another case of the tool not being the reason I didn't use it very much this year. With my writing output way down I found myself using Ulysses a lot less than I'd hope. Not really Ulysses' fault. It's a well made app that has left me with almost nothing but positive feelings. And yet, it's another one that is currently in the process of being ingested by Obsidian. Over the past few weeks it felt weirdly artificial to have my note-taking and my writing happening in two separate apps so I'm trying to do all my longform writing in Obisidan for the foreseeable future. We'll see if it sticks.

Things (macOS/iOS)

Task Management
Things remains my favorite app and the linchpin to my personal productivity system. I occasionally need to do some annoying workarounds when I’m collaborating with colleagues on a shared project, but I think I’ve mostly figured out how to do it in a way that minimizes duplication. Other than the lack of collaboration functionality, Things remains an absolutely delightful piece of software. Fast, rock solid, full of whimsy… there’s not much more I can ask from a fundamental tool in my toolbox.

Carrot Weather (macOS/iOS)

Weather
Sometimes I'm annoyed by how much I pay for this app and I try to get by with the default weather app for awhile. I always come back to Carrot. It's too good. I'm not even talking about the snarky personality and witty retorts that it's known for (if you've never heard of Carrot this is probably a confusing sentence for you). It's the insane level of UI and data customization options that keeps me coming back.

Instapaper (iOS/browser) & Matter (iOS/browser)

Read Later
I'm pretty sure Instapaper is the longest continuously used app on my phone. I've tried its competitors a handful of times here and there, but always found myself coming back to the simplicity of Instapaper. That's why it feels somewhat momentous to say that I'm in the process of moving away from it, again, but this time I'm pretty sure it's going to stick. Moving to Matter has allowed me to get my newsletters out of my email, my RSS feeds out of a dedicated app, and unite basically all of the internet-based reading I do in one app that is actually a pleasure to use. We'll see if I'm still writing about Matter glowingly when I do the 2023 version of this article, but for now I've put Instapaper in a drawer and am living my best Matter life.

Unread (iOS)

RSS
See above. Recently murdered by Matter, too. However -- it is very good and if you're looking for a standalone RSS reader Unread should be near the top of your list. I used it every day basically all year and it's going to take awhile for me to break the muscle memory that my fingers learned with this app.

Kindle (iOS)

Ebooks
I bought 99% of my e-books on Amazon this year because although I'm always hearing the siren song of going full Apple, it gives me the option of reading on a Kindle or on my phone through the Kindle app (whereas buying on Apple Books would limit me to my phone or an iPad — which I don’t even own right now). The Kindle app has gotten better and my busted ass Kindle Oasis is still chugging along. I think I may have finally put the Apple Books vs. Kindle battle to rest.

Audible (iOS)

Audiobooks
I paused my membership for much of the year in order to work my way through a backlog of credits I somehow accumulated. I like to always have one audiobook going at all times and depending on how engrossing I find the book, I'll either fly through it in a couple days or it will sit on my device for months. The Audible app itself is fine and generally stays out of the way, which is more or less what I want from an audiobook app. I wish I could populate my wish list with my Amazon wish list, though. Feels stupid to have to manage two different wish lists for books (albeit in different formats) when they are part of the same company.

Magnet (macOS)

Window Mangement
I love this little app even thought it's silly it even has to exist. My Mac feels incomplete without this running because I'm constantly throwing windows against the edges and corners of my screen to auto-size sindows into quarter-screen and half-screen modes. macOS should just let you do this but until it does Magnet will be one of the first things I install on every new computer.

Slack (iOS/macOS) & Discord (iOS/macOS)

Work Chat
We continue to use Slack at The Ready for all our internal communication. It’s fine. It’s an appliance at this point. I’d rather be in Slack than in email. Discord is my Slack but for crypto/DAO related stuff. I like it less than Slack but it is also fine.

Google Docs (browser)

Work Document Creation
We continue to use Google Docs at The Ready, although our usage has been trending down as we lean into Notion more and more. It's still a big part of my day, though. It meets the bar for most of my work tools -- it mostly stays out of the way and lets me do what I need to do without adding unneeded frustration.

Obsidian (macOS/iOS)

Persistent Note Taking
Obsidian has already shown up in a couple places in this article, but I suppose it should get its own call out, too. In my 2021 recap I talked a little bit about starting a "digital garden" or "Zettelkasten" system in Obsidian. I've gone back and forth since then about whether I want to invest the time and effort into actually creating a system like this. After reading Tiago Forte's "Building a Second Brain" book I think I finally have the bones of a system that I can work with for a long time. Since then I've been regularly interacting with Obsidian and as mentioned above, am trying to move more of my ad hoc writing and note taking to it as well. I'm excited to see what role this tool plays in my life in 2023.

Notion (iOS/macOS)

Life Dashboard/Shared Project Management
We've used Notion as our central knowledge repository at The Ready for the past few years and it has generally been a good addition to our tool box. I’ve also spun up a personal instance that Emily and I use for shared life projects and reference material. I also moved most of my personal and financial tracking spreadsheets out of Numbers and into this personal Notion account. It has definitely grown into more of a shared "life dashboard" over the past few years.

1Password (iOS/macOS)

Passwords
Emily and I have really leaned into using the Shared Vault feature of 1Password this year. It’s nice to be able to put logins to services that we both need in a place where we can both easily access them without having to pester the other person. Sometimes I think I could or should get buy with just the built-in password features of iOS and macOS, but I think we’d miss the Shared Vault too much. If iOS/macOS handled family passwords better, that might make me leave 1Password.

Zoom (macOS)

Video Chat
99% of The Ready’s virtual meetings continue to happen in Zoom. Currently working with a client who uses Microsoft Teams and it makes me incredibly thankful that I’ve mostly gotten to use Zoom up to this point.

Rocket (macOS)

Emoji
Rocket lets me easily add emoji anywhere I can type. Like Magnet, my computer feels like it’s broken if this isn’t running.

Strava (iOS) & TrainingPeaks (iOS)

Training Data
I’ve gotten extremely into endurance sports in the past year and Strava is my go-to tool for keeping track of all the data I generate and connecting with a handful of friends who also train. I use TrainingPeaks with my coach which allows him to schedule workouts for me and see the data after I finish them.

Streaks (iOS)

Habit Tracking
I went for a big chunk of the year not using Streaks to track my daily habits, but not because the tool isn’t good. It was more of a personal experiment to see if not putting pressure on myself to track those things might be good for my mental health. As of a couple weeks ago, it’s back on my phone’s home screen.

AutoSleep (iOS)

Sleep Tracking
I’m honestly skeptical of the quality/validity of the data AutoSleep collects, but I’ve been using it for so long at this point I feel like it’d be silly to stop. I don’t put too much credence into what it tells me about my sleep quality, but at the very least I think it helps keep me accountable to going to bed and getting up when I say I want to.

Day One (macOS/iOS)

Journaling
I haven't journaled as much as I wanted this year, but that's not really Day One's fault. This is another piece of software that is in a precarious moment because of my interest in Obsidian and the realization that it becomes a more powerful tool the more data I can feed into it. I realized that the writing I tend to do in Day One is often early drafts of things that started as streams of consciousness but ultimately become articles. That's the type of thing I want with all my other notes -- thus, Obsidian. We'll see...

Backblaze (macOS)

Backup
Backup is one of those things that you should never have to think about -- until you do. Backblaze is always running silently on all my computers, waiting for the day where it can save my bacon.

Audio Hijack (macOS)

Audio Recording
I haven’t put Audio Hijack in the yearly recap before, but I’ve been using it for years to record Fields of Work and now Ready to DAO It (internal The Ready podcast). It’s one of those tools where I know I’m using 1% of its power — but I’m okay with that.

Garage Band (macOS)

Audio Editing
All podcast editing happens in here. Similarly, I barely understand how it works, but I’ve carved out one specific workflow that seems to work pretty well for editing and publishing podcasts.

Flighty (iOS)

Flight Tracker
Flighty reminds me of Things and Fantastical in that I feel like I’ve been using it forever and that the level of polish on this app makes it stand out. I don’t travel quite as much as I used to, so I don’t use it as much as I once did, but I still keep it around and enjoy using it.

Apple Maps (iOS)

Maps & Directions
Apple Maps + CarPlay + Apple Watch = the simplest and best way to get turn-by-turn directions, in my experience. Haven't opened Google Maps all year, I don't think.

Letterboxd, TV Time, Goodreads, GameTrack

Media Trackers
I like to track what movies I've watched and want to watch, what TV shows I'm watching and want to watch, what I'm reading and want to read, and what I'm playing and want to play. These are the best options I’ve found for each. They also hold my various media backlogs so I won’t forget the recommendations that I collect from various people and places.

Due (iOS)

Reminders
There are a handful of what I call Life Scaffolding reminders that I need to see on various rhythms to make sure I’m taking care of super mundane stuff (water plants every Sunday evening, do laundry every Saturday morning, etc.) and Due is my favorite app for that because it will incessantly remind me on whatever cadence I want until I take action (whereas the default Reminders app just reminds you once at the appointed time).

Apollo (iOS)

Mobile Reddit
I’m trying to use Reddit less and Apollo actively makes that goal difficult because it’s such a good app. If Reddit is part of your information diet do yourself a favor and check out Apollo.

Mela (iOS)

Recipes
I don’t regularly cook new recipes (although I tell myself I should) but I do have like three recipes that I cook frequently enough to remember the basics but not frequently enough to have fully memorized. Those recipes live in Mela. Someday I’ll be the type of guy who has a huge library of recipes that he’s regularly trying and Mela will be the perfect tool. For now, it’s where I go once a month to look up whether my pancake recipe requires baking soda or baking powder.

Substack

Newsletter Distribution
It’s where I write my newsletter. It seems to be where most people write their newsletters. I only interact with it when I have a new newsletter ready to send and I have to copy and paste it into the web app and hit send. It’s fine?

Squarespace

Website Hosting
It’s where SamSpurlin.com and FieldsOfWork.com live. It’s fine?

FastMail

Email Hosting
It’s where I pay to have my sam@samspurlin.com email hosted. It’s fine?

NordVPN

VPN
Sometimes I have to use sketchy public internet and turning on NordVPN makes me feel a little bit better about it. A couple times a year I need to convince ESPN+ I’m trying to watch a hockey game from New Mexico so it won’t blackout the game when the Red Wings play the Capitals in D.C.

Mural

Shared Whiteboard
If I’m hosting a virtual meeting or a workshop there’s a good chance we’re going to be in Mural together. It has become a huge part of my toolbox over the past couple years. It can be pretty janky and I feel like I kind of just fell into it (instead of comparing/contrasting it to other options) but it feels okay.

Pitch (browser)

Collaborative Presentation Design
A relatively new tool at The Ready. Instead of passing around Keynote files (huge, not easily worked on simultaneously) or Google Slides links (barf), we’ve been using Pitch. Honestly, I haven’t built much in it yet, but I’ve definitely presented and tweaked lots of work my colleagues have done in it. I’m a fan so far.

Murmur (browser)

Organizational Governance
The Ready spun out Murmur a couple years ago and in the past year the tool has really come into its own and become a major part of The Ready’s tech stack. It's for helping organizations make and store agreements about how they work together.

Loom (macOS)

Video Messages
I’ve tried to lean into creating super short but dense asynchronous videos as a communication tool with colleagues and clients this year. Loom makes it super easy.

Gather (macOS)

Virtual Office
I’m currently running an experiment with Gather at The Ready to see whether a “virtual office” is something we could benefit from. Early reactions are positive!

A Few Parting Thoughts

• Default vs. Best is still an active battle I find myself occasionally waging in my brain from time-to-time. Usually when I’m avoiding some sort of uncomfortable truth about what I should actually be doing or thinking about. I've proven to myself that I can get my work done using only the Default apps that come with my computer (for the most part) but it's not particularly joyful or enjoyable. Luckily, Apple, as a company, has been pissing me off recently. This has been helping me let go of the idea of going “all in” on their software & services.
• I'm always looking for ways to simplify and use fewer tools and services while still using the best tool for the job. It's interesting that Obsidian is currently in the process of eating several apps I used a lot in 2022: Ulysses, Bear, and maybe Day One. Matter ate three functions that were handled separately in 2022, too: read later (used to be Instapaper), newsletters (used to be in my email inbox), and RSS (used to be Unread). I think I am okay with this. Is there a future where Spotify would ever eat my podcasts and audiobooks, too?
• Best software is fast software. Best software feels like an extension of my mind and body. This is what makes me love Things and Fantastical so much. So damn fast.
• Started playing with Focus Modes on iOS a little bit in October. Other than the default Driving and Sleep ones, I set up a “Done Working” Focus Mode that automatically starts at the end of my work day and ends the following morning. It prevents work notifications (Slack, Email, Discord) from coming through. There’s probably more I could do with this at some point, but even this extremely small feature has been useful so far.
• It feels good that the vast majority of the tools listed above are not brand new. Most of these have been in my tech stack for many, many years at this point. I think I would be very okay to see this list remain mostly the same when I sit down to write next year's version of this article.

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I recently celebrated my seventh anniversary at The Ready. I’ve been involved with basically every aspect of our business (being the first employee means you kind of don’t have a choice but to wear a lot of hats) but the vast majority of that time has been spent as what we call a “Transformer” — an organizational transformation consultant working day-to-day with our clients. This has spanned countless standalone workshops, many light touch advisories, and several intense and deeply involved long-term transformation projects. This means I’ve spent much of my time as a member of a client-facing duo, a lot of it has been in solo engagements, and some of it has been as a leader or member of a larger team. I’ve done a lot, learned a lot, experienced the depths of burnout, the highs of full engagement, and basically the entire gamut in between (fortunately, with a definite weighting toward the positive end).

Anniversaries are a natural time to be reflective so I’m going to use this writing exercise as a way to figure out what I believe about my career path and also as a model for how you can think about your own career evolution. I believe I have control over the majority of the decisions that create the life I’m living and career I’m building. Since I believe that, it’s imperative I check-in with myself from time to time about how things are going, where I think I want to go next, and what I might want to try in the future.

Instead of taking each of those questions in turn, I’m going to instead look at what I think the “adjacent possible” looks like for me with where I’m currently at in my career. Across each of these scenarios, I’m going to ask myself:

1. What emotions come up when I envision myself in this future?

2. What would I miss about this option if I don’t choose it?

3. What pushes me away from choosing this option?

Scenario 1: Keep on Keeping On at The Ready

The obvious option is to keep doing what I’m doing at The Ready. I don’t know how else to really say that what I do at The Ready, in almost every aspect, is my dream job. We exist to change how the world works and we use ourselves as the first and best test environment for a better future of work. Fully self-managing, self-set compensation, fully distributed, great benefits, three times per year in-person retreats in excellent locations, crazy access to well-known clients who trust us to work on gnarly problems… it really doesn’t get much better for consultants.

The emotions that swirl around inside me when I think about another seven years at The Ready are primarily safety and familiarity. It’s what I know and I think I’ve developed legitimate skills that make me desirable as a partner to my colleagues and my clients. That’s not to say that I have universally positive reactions to these quite positive feelings. I’ve come to mostly distrust feelings of comfort and familiarity when it comes to career growth. Most of the best things that have happened to me regarding my career have been the result of stepping into the unknown and taking risks — leaving my teaching career to go to graduate school and then dropping out of my PhD program to move across the country to join The Ready are the two biggest examples that have worked out incredibly well.

As I write this, I’m realizing that the fact that I think I always need to be doing something scary and unknown in order to feel like I’m doing the “right” thing in my career is probably a fruitful topic of conversation to have with a therapist and not something I should just accept as right. Nonetheless, I’m going to feel my feelings and say that the fact that The Ready feels like the safe option puts me a little bit on edge.

If I were to move away from The Ready I would inevitably miss some of the things that makes this my dream job. I can’t think of any other organization where I’d have as much freedom and as little oversight as I do at The Ready. The only way I could get more of these things is if I worked completely for myself. Even then, it wouldn’t be that big of a change to my day-to-day work.

If I’m being honest with myself, I know I’d miss the steady paycheck, too. It’s not sexy to say, but my paycheck is a huge part of why I’ve never even considered something other than The Ready. We are well-paid for what we do, especially for early to mid-career consultants. I think I see a bit of an earnings ceiling given our current financial system, but I’m not in risk of bumping up against it anytime soon.

Finally, obviously, I’d miss many of the folks who I’ve come to call dear friends. We’ve grown beyond the point where I have a personal relationship with everyone who works at The Ready, but some of my best friends are colleagues I met at The Ready. The overall calibre of person we attract and the hiring process they have to go through means I’m surrounded by nearly universally stellar folks.

As I already mentioned, I’m inherently skeptical of anything that feels like the obvious or easy answer. Beyond that, though, are there other things that are pushing me from sticking with this scenario? On good days, this work feels radically impactful and meaningful. On bad days or weeks, though, it feels frustratingly ephemeral and hit-or-miss. If things aren’t catching on at the client, if the bureaucracy is too resistant to our efforts, or if the myriad of other petty frustrations that emerge when doing client-facing work or while operating in a self-managing organization start to pile up, then I can feel my energy and motivation to do this work dissipating. Is it worse than the frustrations that come with any job? Unlikely. Do they exist? Absolutely.

Beyond the petty frustrations, organizational change work can be truly emotionally draining, too. Most days are marked by high intensity human-to-human interaction — whether internal team meetings to figure out and prepare for upcoming moments with the client, client meetings where we’re facilitating or otherwise in charge of the design and flow of a high stakes meeting, or hours or even days long workshops where we’ve often designed, from scratch, multiple high impact and contentious conversations and activities for some of the most demanding and difficult people on the planet — senior executives. I’m good at all of these things, but they come at a cost. I’m an introvert at heart and while I can turn on my extroversion to facilitate a workshop or a meeting, it feels like I need more and more time in between these moments to fully recharge my introvert batteries. If I had my druthers, I’d spend 80% less client-facing time than I currently do.

Scenario 2: Internal Leadership Role Elsewhere

I’ve always felt a tinge of imposter syndrome for having never worked in a large bureaucracy like the ones I consult with everyday (other than my extremely brief foray in the American public school system as a teacher). Would I be able to bring the type of change The Ready is hired to bring if I were a leader in a “regular” organization? Would I fall prey to the same things I see the leaders I work with fall prey to? Would the toolset I’ve developed at The Ready serve me well if I had to operate from the inside? I don’t know — and part of me is curious to find out.

This scenario would entail getting hired as a leader at an organization doing something other than what The Ready currently does. It could be a big name organization or it could be something smaller. In either case, it would be more about the role and whether it has enough positional power to actually let me bring interesting and worthwhile changes to a meaningful segment of the organization.

When I check in with the feelings that come up when thinking about the future where this is what I’m doing, I predominantly feel fear, apprehension, and excitement. Like with the feelings that came up in the first scenario, I don’t necessary view these as negative (at least the fear and apprehension aspect of it). I’ve done great things in my career and life when I’ve felt fear and apprehension — but did it anyway. Might that be the case here?

If I didn’t choose this option I think it would feel a little bit like I’ll never know if I can actually truly walk the talk of the org change and org design stuff we talk about at The Ready. I will never know deep in my bones what it is like to work for a broken bureaucracy (yes, I know how weird it sounds to put this down as something I might have to give up if I never pursue this option).

I also wonder if not going down this path means I won’t be able to open a level of compensation that may be beyond anything The Ready would ever be able to pay me. As I mentioned in the first scenario, I’m nowhere near that hypothetical earning ceiling yet, so this is a truly hypothetical situation that wouldn’t come into play any time in the next 5-7 years.

As far as what pushes me away from this option, there’s almost more than I can feasibly list. First, I know I would hate the lack of autonomy. I don’t have a boss at The Ready and any organization who would hire me would inevitably put me into some kind of organizational structure where someone is my boss. I hope I would learn to operate in that environment, but I know I’m dispositionally disinclined to work well in a highly hierarchical environment. In a similar vein, although I’m interested in bureaucracy from an intellectual and theoretical standpoint, I know that working in one day after day would wear me down to a nub quickly. As an external consultant I’m able to retreat from the client’s bureaucracy into the warm embrace of The Ready when it all becomes too much. That isn’t an option when that bureaucracy is your one and only work home.

Lastly, I can’t actually see myself being qualified for many, if any, senior leadership jobs at non-consulting organizations. At least, I’m not an obvious fit. I didn’t go to business school and I don’t have the bureaucratic experience I suspect you need to even stay afloat in many organization like that. I’m not sure how much seven years at a totally weirdo of a self-managing organization translates into the world of “regular” organizations. I don’t think I could be a Chief People Officer without any real HR experience. Chief Operating Officer? Maybe, but unlikely. CEO? Maybe in the right situation. The only obvious one would be some kind of Chief Transformation Officer but even that seemingly perfect job title often means something quite different than how we think about transformation at The Ready.

Ultimately, I don’t think this is a scenario I really need to think about because I’m not inclined to spend any effort making it happen. If something interesting were to fall into my lap by way of a friend, acquaintance, or recruiter then I would at least take a look at it. Even then, my criteria for whether it would be worth making the jump would be incredibly stringent. But everyone has their price, right?

Scenario 3: The Indie Shift

I always assumed I’d be an indie of some sort. When I started making money from my first website in 2009, I figured I’d be doing some version of that for the rest of my life. Even after going to graduate school, I figured I’d have some kind of solo coaching/consulting/writing endeavor that would form the cornerstone of my career. It was while I was studying independent work as a research project that I became aware of holacracy, sociocracy, and other fascinating organizational theories. Once I found The Ready, I put the dreams of an independent career on the shelf so I could focus as much as possible on building this company. Even while pouring myself into The Ready, though, I’ve always kept one foot in the indie world by writing as much as I can, particularly through my The Deliberate newsletter. Sometimes I catch myself thinking and feeling that The Ready is still just a detour from the indie career I’m supposed to be creating for myself.

The emotions that come up when I think about having successfully shifted to this scenario are pride, authenticity, and excitement. The emotions that come up when I think about the process of shifting in this direction are dread, fear, and anxiety.

If I never end up doing this, it somehow feels like I’ll be neglecting a part of me that has been a large part of my identity for a long time (even while working full-time for an organization for the past seven years). It feels like I would miss out on the best opportunity to ever craft a work situation for myself where I would truly have full control over my time. I’m pretty sure I’ll always think about what I could have done as an indie and regret never taking a true crack at it.

That being said, it would be unequivocally stupid for me to shift hard into an indie career at this moment. The Ready already gives me almost complete control over how I spend my time so I’m not really sure my day-to-day working life would actually look much different if I was “working for myself.” I’d be doing largely the same work without the nice paycheck, nice colleagues, or any of the other world-class support that you get when working for The Ready. What’s the point?

The fact that I haven’t made major strides in this direction, even while holding down a demanding day job, also makes me think that it would be foolish to make any drastic decisions in this direction. I’ve definitely read stories of people who drew a line in the sand and said, “After this day I’m 100% indie and I have no choice but to figure it out.” I admire that, but I don’t think that’s for me right now. I’m still supporting my wife through the last part of her graduate school work, we are thinking about starting a family soon, and we both have enormous student loan bills that need paying. Doing anything to radically negatively affect my income in this moment is a non-starter.

That being said, this strikes me as the type of thing that can be built slowly over time until the shift to it becomes the obvious thing to do (if I want to) rather than needing some kind of leap of faith. The delicate balance I need to walk, though, is figuring out how to keep chipping away at the work that lays the foundation for this at some point in the future without letting it either a.) distract me from work at The Ready or b.) make me feel like I’m continuously failing by not doing enough. The latter of these two options has been a historically difficult path for me to navigate.

Scenario 4: The Wildcard

Must my career continue down the organizational consultant/coach route? All three scenarios above are basically just reformulations on the same raw ingredients (with maybe a bit more ambiguity in the actual work to be done in Scenario 3). Should I be casting my net wider, though?

A major mid-career shift would need to have some extremely excellent reasons for making it. Since I already love what I do, it’s not about escaping something that is destroying my soul. It wouldn’t even be about increasing compensation as I’m already well compensated in my current line of work and there’s still ample room to grow, if I want it. Instead, it would have to be about avoiding some kind of inevitable AI/automation related redundancy or simply the desire to do something different.

I don’t think what we do at The Ready is at threat for any kind of imminent destruction by AI. If there are ever organizations comprised of people then there will be organizations who can benefit from the expertise that we bring (I think). Then again, how many people predicted that illustrators would be at the verge of being replaced by AI before the recent explosion of DALL-E and the other AI image generators of the past few months?

If I wanted to absolutely future proof my ability to make a living, what would I do? I think it would be re-training as a software engineer. I’ve always been deeply interested in tech at least from a culture and philosophy standpoint. I’ve always liked the idea of creating software and have made a couple half-hearted attempts at teaching myself the basics. I definitely have some internal scripts telling me that I don’t have the mind or ability to learn to code, but there’s very little evidence from my life that validates those ideas. It would be hard as shit and probably very frustrating, but I’ve shown myself that I can learn anything I put my mind to needing to learn. Is that what I should be doing here?

(There’s an interesting digression I could go on here about how the best way to future-proof my career from AI obsolescence would be to double down on the only thing that AI is never going to be able to replace — me — which means Scenario 3 , not learning to write software, is actually the most future-proofed path forward.)

A Third Way Emerges

Obviously, there are options outside of the four I just described and as we like to teach our clients, there’s almost never a simple binary decision to be made. There’s always a third way. What’s the third way between, or mixing, these scenarios?

I probably should’ve led with this in case any of my colleagues at The Ready have been reading this article with increasing levels of concern; I’m not leaving The Ready. However, I think there are things that each of the scenarios I described above that are worth trying to incorporate into how I craft my roles at The Ready to make my work more sustainable, enjoyable, and impactful. For example, I’m going to continue looking for opportunities to architect and advise projects rather than spending all my time in the day-to-day client work. As I continue to develop expertise in this work I want to find ways to leverage this hard won experience into ways that are more valuable to The Ready and more interesting and engaging for me.

This also means leaning into the opportunities to direct the entrepreneurial energies I described in Scenario 3 into new opportunities at The Ready. We’ve never conceptualized our work as solely delivering consulting services. We’re actively experimenting with products, new services, and other variations on our tried-and-true approaches. The recent work we’ve undertaken in the DAO/web3 space is a great example of this. It has helped me better understand what I’m good at and what I like doing. I like being on the cutting edge of figuring out what’s possible in a new space. The first couple years at The Ready, specifically the first few months where the team was extremely small, was an absolute peak experience for me. The DAO/web3 work has reminded me that this is where I tend to be at my best. Where else can I do that at The Ready?

Just because I’m not planning on leaving The Ready any time soon doesn’t mean that I can’t keep developing my own personal brand through writing online. I know that when I’m writing regularly I feel the best about myself across almost all aspects of my life. I’ve played with the causality of that relationship and I’m 95% sure that writing is actually the cause of those good feelings, not the result. Writing at SamSpurlin.com and for The Deliberate needs to continue being something I do more regularly than I have been recently. These may become the kernel of an indie career some day and they may not. Nonetheless, I need these outlets in my life for my own psychological health, if anything else.

Scenario 2 is the one that feels most unknown and the one that I should be most careful writing about in absolutes. What I can say about moving to any kind of internal role at a non-consulting company is that this is not something I am ever going to actively search for. But I would be disingenuous if I said that I wouldn’t leave the door open for surprising opportunities. If a former client, friend, or acquaintance thinks I’d be the right fit for an interesting internal role I’d take a good long look at it even though my situation at The Ready is already as ideal as I can really imagine a job getting.

Somehow, it feels like I’m “cheating” on The Ready by even saying it, but I think it’s worth saying it out loud. The decision to keep doing what I’m doing should be exactly that, a decision. And not just a decision I made once a long time ago when I was in a different phase of life, but a decision that I revisit and re-confirm regularly. Inertia is a scary force. If I’m going to stay at The Ready I want it to be a conscious decision with real trade-offs, not just the thing I do because it’s the only thing I know. I welcome the opportunity to regularly look at my decision to remain at The Ready, hold it up against something truly compelling, and (likely) choose to keep doing it. It feels like the only healthy way to stay at one organization for a significant amount of time and not become complacent.

You’ll notice that I didn’t spend any time laying out a grand unified vision for the evolution of my career. I did that once. Nothing I currently do was part of that vision, and yet, as I’ve said many times throughout this article, I love what I do right now. I’m much more interested in looking at the adjacent possible and figuring out how to consistently attain that, rather than following any sort of master plan. As long as I’m consistently feeling like I’m stepping toward the unknown, making a real impact with the work I’m choosing to do, and feeling like I’m building mastery I think I can’t be too far from where I need to be.

This article, and this experiment more broadly, are part of the project that I’m trying to optimize my environment and my mental state to make progress on. This thread is a good overview of the intention. Broadly, I absolutely must make progress on capturing, codifying, and articulating the swirling ideas that make up The Deliberate. My feint toward writing a book proposal at the end of last year’s sabbatical was my first true attempt at figuring out whether the things I’ve been writing and thinking about for the better part of 11 years could be coalesced into something coherent. The proposal itself was a failure in the sense that I didn’t finish it or shop it around, but it was a grand success in that it helped push me in a more productive direction in how I think about all of this stuff. I realized that I don’t want to contrast it against “self-help.” I realized that it’s about more than just self-experimentation. I realized that it’s about uniting an intense desire for personal growth without using dissatisfaction or guilt as the driving force. It’s both intensely philosophical and almost simplistically practical.

Since then I’ve been writing a bit, tinkering with the idea of Deliberate Patterns and a public Deliberate Pattern Library quite a bit, and feel like I might be ready to take another stab at pulling these tangled threads into something more than the Gordian Knot they seem to be right now. Perhaps the attempted book proposal in September of last year was the slice that slew the Gordian Knot and I’ve been organizing the fallout since then. Can I do something with these newly separated, discrete, and separated threads? That’s what this experiment is all about.

Frankly, it’s also about doing something to honor these ideas enough that they will finally leave me alone. I’ve felt like I have something profound to say about these ideas for the better part of a decade and not figuring out the words — or more accurately, not making the time and space so that I can figure out the words — is  driving me crazy. I need these ideas to leave me alone. I need to give them a home so they can stop living in my head.

Sometimes Deliberate Patterns are about making small tweaks to your life. So small that they seem almost inconsequential and yet, in my experience, these small tweaks often open up new lines of inquiry and self-knowledge that I could not have predicted. This experiment, Monk Mode, is not that. This is more in the realm of what we would call “radical change at (relatively) non-radical scale.” In Cal Newport’s parlance from Deep Work, this experiment is a Grand Gesture. A Grand Gesture is a seismic shift in your normal routine that signifies and amplifies the importance, in your own mind, of the thing you’re setting out to do. Monk Mode is deliberately disruptive because I need my brain to treat this project with the proper gravity.

So, what about Monk Mode is going to be so disruptive? Here’s my current list of “rules” and routine modifications for this endeavor:

• Twitter, Reddit, Instagram, all podcasts, and 99% of all my notifications are no longer accessible through my phone.

• I need to complete at least one hour of a focused (no distractions) work session every day.

• All workouts/triathlon training must happen without headphones.

• I need to complete at least one 20 minute meditation session every day.

• I need to listen to the same music during my focused work session (Tycho) every day.

• I need to do a very brief written reflection (just a couple sentences) before I go to sleep about how the day went.

• I need to put my Playstation, Switch, Oculus, and guitar in a closet.

Everything in the list above, and the new things I will undoubtedly add to it over the coming weeks, is about creating space and silence. Difficult and complex writing endeavors require both of these things (at least for me). The ideas I need to develop and eventually cohere into something sensible are not going to be served by a surface-level effort any longer. I’m already good at surface-level. Almost everything I’ve done for the past decade is a result of my ability to do good surface-level work. But it’s time to see if I can do something a little bit more complex and a little more rich than my normal fare. I need these ideas to simmer like a good chili — low and slow to let the flavors develop into something more than the sum of their parts.

This experiment is happening along side my normal and relatively intense (at least cognitively/intellectually intense) day job at The Ready. Hence the relatively low time commitment to focused work on this project. I hope I can muster more than an hour every day, but even just an hour of focused effort a day paired with the space and silence for the ideas to keep marinating in between sessions will represent a phase change in the quality of attention I’ve given this project in… probably ever.

And as far as the project itself goes? Well, I’m letting that emerge. I don’t know if this thing needs to become a book or a series of articles or a series of talks or some other creative output that I haven’t even conceptualized, yet. What matters is that I create something that feels like the canonical version of my best thinking on these topics. I want it to be something that is inspiring and useful to the people like me who find this way of thinking and living interesting and exciting and would love to connect to other people who think this way and want a bit of a framework to work with. Basically, I want to write what 11 year ago me was looking for and unable to find when he first started down this path of thinking about the intersection of attention, personal development, and philosophy. If I can make that version of myself happy then I think this version of myself can be happy, too.

Subscribe to The Deliberate to stay up to date on how this experiment, and all my future work around these topics, goes. Twitter is also another place to get a slightly more unfiltered look into what I’m thinking about and working on.

To quickly set the stage, my fitness starting point in September 2021 was:

• No real swimming ability. I could functionally swim, like, to survive. But swimming more than 50 meters without my heart exploding seemed impossible.

• No real running ability. Around the time I started training I could maybe run 1 or 2 miles without my shins hurting and my lungs exploding.

• I did not own a bike. But I did have strong quads from years of ice hockey so I thought I would maybe be okay at it?

With the preliminaries out of the way, let’s dig into it.

The race was the Sprint distance (750 meter swim, 12 mile bike ride, 3.1 mile run) and it was held a little over two hours away from my home in Northern Virginia. Luckily, I was not really worried about my ability to complete any of the three disciplines. I regularly do workouts much longer than each of these distances at this point — although I had never done all three disciplines in one day. The other question mark was the swim. I train in a pool where swimming in a straight line is a matter of following a painted line on the bottom of the pool and the water never gets colder than 80 degrees. This swim was done in a lake where I could see nothing when I looked down and the water temperature was in the low 60s. I had done one 10ish minute swim in the pool with my wetsuit and one 15ish minute swim in a much colder lake two days before the race. This would definitely be my longest open water swim up to this point and while I knew I could do the distance, I also knew there was no grabbing onto the edge of the pool or standing up in chest deep water to catch my breath.

Friday

Emily and I wrapped up our work days a couple hours early, loaded up our car, and made the two and a half hour drive down to the race location. The aim was to make sure we could find it, pick up my race packet, and generally just scope out the area. I should’ve had “drive the bike course” on my list of things to do (foreshadowing). 

We arrived, parked, and I flew through the packet pickup line in a matter of maybe 45 seconds. Kinetic Multiport runs a tight ship! The only notable thing about packet pickup was that I received race number 404, which made me audibly laugh when I received it (much to the confusion of the nice volunteer who handed it to me). I couldn’t decide if it was a good or bad omen. Either way, my tech nerd friends on Twitter appreciated it.

After walking around the transition area, seeing the swim start and exit, and generally taking in the sights, Emily and I went off in search of dinner. We wanted something simple and familiar so we found a Panera and I had a small bowl of soup and a steak sandwich. From there, a quick drive to the hotel and early to bed!

Saturday

Pre-Race & Warmup

Since this race was only an Olympic and Sprint, it didn’t start until 9:00 (and the Sprint participants didn’t actually take off until 9:30). That meant I was able to get up at my usual time of 6:00 and eat my usual breakfast of oatmeal and coffee around my usual time of 6:15. Pretty perfect timing, digestion-wise.

We got in the car a little after 7:00 and made the drive out to the race location (a scenic 30 minute drive through the woods and fields of Virginia). Parked, got my bike off the car rack, and headed straight to transition to find a spot and setup my gear. As this was my first ever triathlon, I wasn’t quite sure what the optimal layout was for all my stuff. I definitely copied some of the folks around me but mostly just thought it through from first principles and then stood in front of it all and visualized myself going through each transition and putting on/taking off each piece of gear. I was a little worried I’d forget I needed my helmet on and buckled before handling my bike, so that was on the top of everything. I also put a piece of red electrical tape on the seat of my bike, thinking it might be easier to just look for the red tape when I’m stumbling through the transition after my swim and realizing that everyone’s bike kind of looks the same. I ended up not needing it because I found a pretty good landmark for my spot (first rack after the volleyball court).

When I felt that I more or less had everything laid out the way I wanted I packed up my backpack with my wetsuit and other non-transition-area paraphernalia and found Emily to go kill some time. We had well over an hour before I needed to start warming up so we just found a picnic table for a bit and walked around. Hit the port-a-potties once or twice and once it got close to the Olympic start time, I started doing some light calisthenics to warm up and threw on my wetsuit. With the Olympic athletes starting their swim, I went to a place on the beach far from where they were and got into the water and did maybe 100-150 meters of warming up. Mostly, I just didn’t want the first time I touched this pretty cold water to be when I was starting the swim. That was definitely a good call.

Swim

The start was a “time trial” start which meant that we roughly lined up by swim speed (“If you’re fast be near the front, if you’re less fast be in the middle, if your’re definitely not fast go to the back”). I was near the back. Every two to three seconds they would send off another person. As I mentioned earlier, this was my first open water swim of any significant distance so the only thing I was interested in doing was staying calm and controlled. I was not shooting for any time. I was shooting for a feeling — I wanted to feel like I could’ve kept going once I got to the end. Everything went more or less fine during the swim. I definitely don’t have my sighting technique dialed in. I only started practicing it maybe a week ago and right now when I do it I either don’t see enough to adjust my trajectory or I break my stroke flow a little bit too much. I had a couple moments of treading water/breast stroking to confirm my orientation, but didn’t really need to resort to any of my “emergency” strokes to get through the distance, which felt good. 

While I’m not sure how much farther I could’ve gone, I did exit the swim with my heart rate and breathing under control — even if I was extremely happy to be done swimming.

(See my Strava activity here).

T1

The first couple of steps coming out of the water were a little wobbly and I kind of forgot I needed to start stripping off my wetsuit until I was well into the transition area. Eventually I remembered that I wouldn’t be riding my bike in a wetsuit and I started clambering out of it as I jogged. I found my bike no problem and was glad I had lathered my arms and legs up with conditioner prior to putting on my wetsuit — it definitely made it much easier to take off. Wetsuit off. Helmet on. Sunglasses on. Put socks on wet feet. I can’t remember if I sat on the ground. I must’ve, because I can barely put my socks on when I’m standing in my living room, never mind after swimming kind of hard for 20 minutes. Bike shoes on. Bike off rack. Jog with bike for a kind of long time until I hit the Mount line at the top of a little gravelly hill and hit the pavement. 

Bike

It felt good to clip into my bike and start picking up speed. While I’m not particularly good at any discipline of triathlon, I think I’m most confident and comfortable on the bike. I don’t have a power meter on my bike, so I didn’t really have a great way to judge how much effort I was putting into it, but I knew I wanted to go pretty hard since it was such a short ride (only 12 miles). I was a little surprised how tired my legs felt initially, but that started to fade as I hit miles 6, 7, and 8. 

As I was getting close to the 12 mile marker, I made a critical error. Because I hadn’t driven the course ahead of time and I didn’t really recognize the area, what I thought was the spot where the Olympic distance people would turn to go off on their second lap as actually where I was supposed to turn to finish my first lap (Olympic-distance athletes did two laps of the 12 mile course and the Sprinters were supposed to do 1). I thought the Sprint finish would be just after this spot. The timing was really unfortunate because as I slowed down to read the signs, a couple of really fast people on expensive bikes whizzed by me and made the left-hand turn where the only part of the sign I could quickly read said, “Second lap.” So, I assumed that was where the Olympic-distance folks were turning to do their second lap so I just carried on my merry way. 

As I hit miles 13 and 14, though, I knew I had made a grave error. I had an initial moment of panic where I wasn’t sure if I should try to turn around and go back or just keep going and do another lap. I didn’t have my phone so didn’t trust my ability to actually find where I needed to go without GPS/map and I knew it would be unsafe as they had only blocked off one lane of the road from vehicle traffic. I was very worried, though, because I knew Emily was waiting for me and I had no way of contacting her to let her know I was going to be out on the cycle course for another 40ish minutes. I think I used that anxiety to fuel myself through that second lap. 

The second time around I didn’t miss my turn off and after a very eventful cycling leg I was ready to be done with my bike.

(See Strava activity here.)

T2

I saw Emily almost immediately upon dismounting my bike and she seemed utterly unperturbed yet still excited to see me. I decided to hold off on explaining what happened and just focus on finishing the race. 

The rest of this transition felt smooth and easy. I realized that T1 feels awkward and hard because taking off a wetsuit is inelegant, no matter who you are. But throwing a bike onto a rack, putting on running shoes, a running belt, and a running hat feels awesome.

Someone tried to offer me water just as I was coming out of T2 and I wish I had grabbed it. Instead, I shuffled my way up the hill and out into the woods for what I hoped would be a relatively quick and easy 5k.

Run

Unfortunately, my confidence about knowing the course was totally shot at this point. I also didn’t hydrate particularly well while I was on the bike because I had only brought one bottle with me (again, thinking I was only going to be out there for like 35 minutes instead of an hour and ten minutes). If I had known I was going to do a 24 mile bike ride I probably would’ve had a gel near the end, too. Anyway, these are the things I was telling myself as I realized my legs felt terrible early in the run. Well, actually, they kind of felt okay at first. It was around the first mile marker that I realized I was not going to finish this thing with total grace. 

The whole first half of the race I was wondering if I even knew where the Sprint turnaround was. Whether maybe they had taken down all the Sprint signage because surely all the Sprint athletes who didn’t do an extra 40 minute bike ride were finished by now. Luckily, my concerns appeared unfounded as I saw the blessed turnaround sign at the approximately 1.5 mile mark and was able to power walk through an aid station where I tasted the best Gatorade I had ever had in my life. 

The last mile and a half were pain (mostly calves and shins but this was also the moments where I realized that while I had Body Glided the shit out of my collar and upper shoulders to prevent wetsuit chafing, I had neglected to apply any to my nipples which I realized were rapidly starting to chafe), but I was able to keep moving at a decent clip, walk through one more aid station with about half a mile to go, and run through the finish line with something like a smile across my face.

(See Strava activity here.)

Final Thoughts

I’m not actually super upset that I messed up the cycling portion of this race. I wasn’t actually racing anybody except myself and I’ve always viewed this race and the one I’m doing in June as existing solely to get me ready for the half-Ironman I’m doing in September. So, in some ways, I’m proud of myself for doing the Olympic distance even though I was not mentally, hydrationally, or nutritionally prepared to do so.

Doing my first open water swim, not missing any key equipment, and not having any equipment failures are all other confidence-boosting experiences from this weekend. On the other hand, it was also a humility-inducing event. I realized that I still have a long way to go in my training to be able to approach an Olympic or half-IM distance triathlon with the same confidence that I brought to this one. I was so done with swimming after 750 meters. I was so done with cycling after 24 miles. I was so done with running after only 5k. That was fine for this race, and I’m proud of how far I’ve come since September of last year, but I have a lot further to go before I get to September of this year.

Ultimately, though, the main feeling I left with from this weekend was that I couldn’t wait to get back into my training next week. If I could come this far in only a handful of months, how much farther can I go if I keep pouring time and effort into this endeavor over the next few months? I can’t wait to find out.

My hockey career died several small deaths before finally dying for good at the end of 2019.

The first death was when I decided to stop playing AAA and go play for my high school instead. The second death was when I played my last college club hockey game at the end of my Junior year of college. The final death was when I received three concussions over the course of a couple years while playing beer league hockey in NYC and DC.

It’s somewhat sad that I managed to play many years of elite hockey (AAA), then several more years of not elite, but still highly competitive hockey (high school and college club) with only superficial injuries (other than a shattered collarbone in high school) and it’s the old man version of hockey that ultimately made me have to step away from the sport for good.

Then again, I probably had lots of undiagnosed concussions. I had my “bell rung” lots of times and lost consciousness after a hit more than once. “Shaking it off” and playing hurt were, and remain, part of hockey culture.

What’s it like to have a concussion?

At first, not a big deal, really. None of the concussions I had were truly catastrophic, I don’t think. I’d have a bit of a headache, maybe a sore neck, and that was it. But the last couple, in my 30s, were something different. In addition to the usual headaches, these ones had symptoms that set in later. Weird symptoms. Symptoms like feeling like I was on the verge of tears, all day, for no reason.

Feeling like I was watching my life as a barely interested observer. Feeling like I was kind of floating a couple inches above my own head, all the time. Feeling like I was going through the motions until I could just go home and sit in the dark.

I noticed it was starting to get easier and easier to reawaken these symptoms, even after quite minor collisions. The death knell to my playing career didn’t even happen on the ice. It happened in the back of a Lyft on my way to a client’s office. We were involved in perhaps the lowest speed rear-ending of all time… but it was enough to bounce my head against the headrest, ever so slightly. And boom. Symptoms, back. Headache. Fuzzy vision. Emotional rawness. The realization that I I can’t keep doing this.

I had already mourned the end of my competitive playing career since I’m pretty far removed from those college days. However, I was surprised how a high enough level of beer league hockey could reactivate some of those same neural pathways as when I was playing with and against some of the best players in the world. Sure, we were much slower than we used to be, but to my brain it felt very similar. Reading the forecheck correctly in order to make a great breakout pass. Playing a 2-on-1 to perfection. Faking a shot and making a backdoor pass. These were all well-established connections in my brain and basically overnight they became completely useless.

But now that my beer league career has come to an end at the end of 2019, I realize I’ve been in the midst of one more mourning process. It was easy to ignore it when we were deep in the throes of COVID. The ice rinks weren’t even open for a long time so it didn’t seem like my decision to stop playing. But I can’t credibly tell myself that story any longer. My beer league buddies are out there playing. My brothers are out there playing. And, to protect my oft rattled brain, I am not. It sucks.

A couple months ago I threw away the vast majority of my equipment — everything except my skates, my stick, my helmet, and my gloves. I knew if I kept everything else around I would convince myself that the head injuries “weren’t that bad” and I’d be finding my way back to my beer league team and inevitably tempting fate again. So, like an alcoholic who wisely doesn’t keep alcohol in the house, I no longer have the shin pads, hockey pants, shoulder pads, and gloves that would let me go out and potentially risk a catastrophic brain injury again.

Looking on the brighter side, I’ve tried to use this decision as an opportunity to explore new hobbies. I’m training for a triathlon now and as long as I don’t fall off my bike, I think my likelihood of getting another concussion is quite small. I’ve done some lessons with a golf coach. Another low impact sport that might let me tap into the competitiveness that used to find its outlet through hockey, but is now mostly just churning around inside me with nowhere to go.

As far as getting older goes, not being able to play a specific sport but otherwise being in great physical shape, is a pretty good deal. Things could certainly be worse. I’m sure there will be other moments in my future where I look back at this “sacrifice” and wish for the day where this was the worst thing I had to deal with. If we’re lucky, I suppose we all get to experience that. Better than the alternative, right?

I don’t have a coherent end to this article. Most of my identity for most of my young life was tied up in playing hockey. That stopped being quite as true as I got through college, into my 20’s, and even less so into my 30’s. Even then, though, I played hockey at least once, sometimes twice a week, basically ever since I graduated from college. That’s gone now. It makes me sad. I used to be more sad, which is probably a good sign. But I’m still sad. Hopefully I’ll continue to be less sad the further I get from the last time I laced up my skates.

The end.

The Problems With Habits

Developing good habits is not the best path to happiness, productivity, success or any of the other things self-help books seem to think you want or need. Don’t get me wrong, having “good” habits is certainly a nice-to-have. All else being equal, I’d rather have “good” habits than “bad” habits. But I can’t even write that phrase without putting scare quotes around “good.” What does good mean? Are good habits universal across all people and cultures? What about for one person but across a long period of time? The fact that there was a period of my life where I was trying to gain weight in order to be a better hockey player, but am now a 35 year old office worker, is only slightly silly evidence that habits cannot stay static but actually need to evolve over time.

If philosophical arguments about what “good” means isn’t your cup of tea, try thinking about some of the other key characteristics of habit change. In most cases, they take a lot of effort over a long period of time to develop. Even worse, it seems like they’re relatively easy to break or lose, too. So, not only do you need to invest a ton of energy into the creation of a new habit (a habit which might no longer be fit for purpose in a relatively short period of time), but one or two off weeks might mean that you have to start over from scratch.

This isn’t even getting into all the weird moralizing that we tend to do about “good” or “bad” habits. Having good habits is too easily equated with being a good person while having bad habits is equated with being a bad person. They are an incredibly blunt, non-responsive, and emotionally charged tool that we somehow feel like we must get right in order to achieve what we want in our lives.

And, from what I can tell, there isn’t much pushback on the fundamental assumption that our habits are what we should be trying to change in the first place. So, I will take that step out onto that ledge and proudly say, “Habit change is for suckers.”

I don’t say that because I think we should all be happy to remain unchanged, unchallenged, or uninterested in growth. I’m not advocating for staying static. In fact, I’m arguing for the opposite. I think personal growth is a fundamentally positive phenomenon that is a cornerstone of what most humans want from their lives. People want to feel like they are becoming more capable, becoming more skilled in navigating their environments, and are better understanding their own psychology. Habits are not the best way to explore and develop these things. Instead, we should treat the “Deliberate Pattern” as the atomic unit of behavior change.

Deliberate Patterns

Deliberate Patterns are like recipes that create action in the world. Inspired by Christopher Alexander’s work on “pattern languages,” they describe moments of conscious and deliberate choosing to act a certain way in a certain environment because you’re curious what effect it will have on you and the world. You could argue that Deliberate Patterns that have become completely engrained into how you behave are actually the same things as good habits. However, this flavor of Deliberate Pattern is such a vanishingly small proportion of all the potential patterns available to you yet they take up far and away the most space in the discourse around personal development.

Instead, I want to shift your attention to the world of Deliberate Patterns that are unlikely to ever become habits — but are still absolutely worth exploring.

The reason non-habit Deliberate Patterns are worth exploring is because every time you try one you learn more about yourself. They are little tests, challenges, or inquiries that knock you a little bit off of equilibrium. They poke you. And in that poking you have an opportunity to watch how you respond. That observation gives you hints about other Deliberate Patterns that you might want to explore in order to further develop an area of self-knowledge. 

A straightforward example might go something like this: You’re curious about what it would be like to change your diet so you decide that twice a week you’ll eat a vegetarian diet. You realize that making that change wasn’t very hard and you’re actually feeling a little bit better physically and mentally. You decide to read a bit more about vegetarianism and then decide to experiment with eating vegetarian every day except the weekend. Later, you decide to fully step into a vegetarian diet because you’ve slowly shown yourself over time that it’s something you’re capable of doing, that it changes your life for the better, and makes you feel like a better version of yourself. The one caveat with this example, though, is that you don’t have to see every experiment through to its logically most extreme version. Even stopping that experiment chain after the first small experiment, eating vegetarian twice a week, would still be worth doing! That slight variation from business-as-usual would be enough to help you learn something about yourself. 

The world is not designed to automatically help you develop this self-knowledge and mastery. You have to create these moments for yourself.

Each new pattern you experiment with shines light on new parts of your identity. You don’t have to permanently adopt a pattern, like how we often think of habits, to get that benefit. Most patterns, even if adopted for only a week, will tell you something about yourself. As you experiment with more patterns you’ll uncover some that are worth integrating into your everyday life. It’s just becomes part of who you are. Others turn out to be useful or interesting but aren’t necessarily something you want to keep doing forever. Some of these you’ll keep in your Deliberate Pattern toolbox, ready to put back into action if and when the time is right. Others, though, you’ll just do once. All of these are good, helpful, and set you on that path toward self-mastery.

What I’m most excited by is what it looks like when there is a publicly accessible list of all the various Deliberate Patterns people have tried, tips for implementing them, and the insights they led to. I’ve started building this here and I hope to make it something the community can contribute to in the near future. For now, though, feel free to poke through the various Deliberate Patterns I’ve written up so far and take them as inspiration for your own experiments. If you do try any of them out, I’d love to hear how they go for you!

In the mean time, don’t overthink it. Just think about something you might want to try differently for a week, figure out how to make that change for a short period of time, and take note of how it goes. At the end, spend a few minutes thinking about and writing what you noticed and what you learned about yourself. You might be inspired to do the same experiment again, tweak it, or drop it entirely and do something else. There’s no wrong answers, just more aspects of your identity and psychology to explore!

Follow me on Twitter and subscribe to my newsletter, The Deliberate, to participate in the ongoing exploration of deliberate patterns and how they can be thoughtfully applied to living better.

DAOs are complex and frequently chaotic environments. As a new organizational technology, there are very few best practices that have permeated across the ecosystem. Everyone is rapidly experimenting and learning on their own. It’s a tumultuous and exciting time for those of us who are energized by the potential of self-managing organizations to fundamentally improve the experience of work for people across the world.

A useful analogy for understanding what is happening within any organization, even a DAO, is that of an organizational, or DAO, “operating system.” Without going too far down a technical rabbit hole I’m not qualified to lead us down, an operating system is the mostly invisible to the user layer that runs between your computer hardware and the software you interact with every day.  What if we extend that idea into our DAOs and how they function? What is the invisible layer of assumptions, principles, and practices that manifest the way we experience our DAOs?

While an imperfect analogy, it has been useful in our work at The Ready as a way to help crack open the typical black box of organizational culture. It gives us a series of levers and intervention points where deliberate decisions can be made about how we want the organization to function. Our current best thinking about organizational operating systems has led us to twelve different areas or modules that interact with each other to create the organizational experience. They are; Purpose, Strategy, Workflow, Membership, Authority, Resources, Meetings, Mastery, Structure, Innovation, Information, and Compensation.

Each field simply holds the space for the principles, assumptions, and practices related to each topic. You can think of each field as a lens through which you can analyze your entire organization to see it in a new light. It allows us to ask questions like: What do we believe about what good looks like in each of these fields? What is our current state within each of these fields? Have we made deliberate choices about how we do these things or are we on some kind of inertial path based on our historical experience in other organizations (or deep-seated assumptions about work and humans)? Are our beliefs and principles across these fields coherent? Or do we believe something in one field that is directly at odds with another (e.g. we want to push as much authority to the edges of the organization as possible but we hoard the most important information to a few key roles)? Are the challenges we’re experiencing in one field permeating across our operating system in unhelpful ways? Is there something we’re doing well in one field that we can translate to another field?

As you may be starting to realize, looking at your DAO through the lens of the operating system metaphor opens up a world of conversational and interventional possibilities. It’s like taking a crystal and holding it up to a boring old ray of sunshine. What was once undifferentiated white light is now a spectrum of discrete colors and intricate patterns. What may have once been a confusing amalgam of behaviors and conversations and conflicts and interactions in your DAO is now something that can start to be understood, and more importantly, interacted with in a productive way.

The DAO operating system and the OS Canvas are both value agnostic tools in themselves. Neither one tells you what your organization “should” be like. You can take the most oppressive organization from history and use the OS Canvas to understand its decidedly negative and harmful operating system. Knowing that DAOs have operating systems doesn’t mean you necessarily know what to steer that operating system toward.

Your intuition has some hints for you, though. As an early contributor to the crypto space, you’ve probably got some individual principles and preferences around openness, decentralization, and humanity that you expect to experience in the DAOs you’re contributing to. At The Ready, we’ve gone a step further and analyzed many organizations who seem to be making surprising and unexpected decisions about their own operating systems — to great effect.

We’ve collected these practices, principles, and assumptions and tried to better understand what unites them. We’ve landed on two major categories that most of these progressive practices and approaches can be sorted: People Positivity and Complexity Consciousness.

People Positive operating systems are built on the fundamental assumption that people are good, trustworthy, and willing to work hard without someone standing over them with positional authority to reward or punish them. These operating systems build structures and scaffolding that honor the humanity of the people who work within them. They push the envelope on what it means to trust people and they deeply question any policy or process that assumes people need to be monitored, coerced, or otherwise forced into specific behaviors. They expect a lot from people because they know people have a lot to give. People Positive DAOs understand that people will behave in the ways that the system expects them to behave: Trusted people act trustworthy, coerced people will be passive unless forced into action, people treated like pawns will treat the organization like a game to be won.

Complexity Conscious practices, principles, and assumptions are about honoring the reality that organizations are complex systems. Complex systems cannot be analyzed and repaired like complicated systems. Organizations are like weather systems or gardens, not broken watches or malfunctioning engines. Complexity Conscious operating systems allow for emergent and unexpected behavior by creating simple rules and guardrails that constrain behavior in useful, yet minimal, ways. They don’t try to overly predict and plan their way into a completely knowable state because they understand complex systems can never be managed like that. They try to create conditions, expertise, and pathways for more robust sensing, steering, and learning along the way. While humans tend to enjoy feelings of certainty, Complexity Conscious organizations understand that certainty is nearly always an illusion and that the only way to truly understand a complex system is to stay in constant, active, relationship with it.

How to Get Started Evolving Your Organizational Operating System

As helpful as the operating system analogy can be, it has limitations. Namely, you might assume that a DAO operating system can be “installed” or “upgraded” like the operating system on your device. In the technical world, operating systems are built by skilled programmers that are released to the public in one fell swoop. With the push of a button we upgrade our devices with the latest software.

The way DAO operating systems change could not be more different. It’s tempting to think that a small group of skilled organization design practitioners or leaders can go off and figure out the ideal operating system on their own — eventually coming back to the rest of the DAO and “installing” it. I wish it worked that way since it would make my life as an organizational design consultant much, much simpler!

Instead, it’s useful to shift analogies and think of an organization as a species striving to survive and evolving over time. Organisms sense and respond to their environment, sometimes creating offspring with useful mutations that allow them to better survive and reproduce in its environment. These useful mutations persist over time while the unhelpful ones quickly drop away. Eventually, we see the species change over time, becoming more capable for its current context. DAOs and their operating systems operate in much the same way. Instead of nature’s random mutation, most of which are not helpful and don’t survive in the species, we can create intelligently deliberate mutations within DAOs by experimenting with aspects of our operating system. The experiments that help us function better are sustained, expanded, and spread across the organization, becoming norms, defaults, templates, rituals, and other cognitive or sociocultural structures. The ones that don’t help are ended and new experiments are spun up in their place. Over time, through a process of continuous and participatory change, the organization’s operating system evolves.

A process like this requires two things that traditional organizations often struggle with: quick iteration and freedom to try new things. Almost nothing happens quickly or easily in traditional organizations, including operating system experiments. DAOs, on the other hand, may actually suffer from the opposite problem – too much hectic iteration without codifying lessons learned and too many degrees of freedom, inadvertently pitting experiments against each other in a way that confounds the results of both. Despite those challenges, though, I will happily place my bet on the organizational technology that allows for rapid iteration, emergent behavior, and an ethos of innovation. DAOs have all of this, and more, in spades. 

Which DAOs will channel this energy into productive paths forward and which ones will spin around their own local maximum until the energy runs out?

Sam Spurlin is a partner at The Ready, a self-managing organization design consultancy dedicated to changing how the world works. He’s on Twitter and is ready to talk about  anything related to organization design, self-management, and DAOs. Prefer to use your voice? Grab 30 minutes on Zoom with Sam here.

Thank you to Alastair Steward and Tanisi Pooran for specific advice that made this article better. Thank you to all my colleagues at The Ready who have helped build these ideas over the past few years and to all other organizational practitioners whose ideas we’ve been inspired by, adapted, and pushed forward.

A year has always felt impossibly long. Something that happens in January and something that happens in December have always felt like they were on opposite ends of an infinite divide. This was even more true when I was a child and the endless expanse of a summer vacation felt like an epoch. But even as an adult I’ve never really felt like all 12 months of a year hang together in a cohesive way.

That is, until this year. For some reason my year felt like a cohesive unit. It certainly had distinct phases, which I’ll get into below, but I’m struck by how it felt like an extremely contained, and brief, moment of time. Perhaps I’m just getting old and experiencing the realities of math and physics (each year representing a smaller percentage of my overall consciousness as I age). I think it might also have something to do with the fact that I’ve now officially gone an entire year using my Week/Month/Trimester Review and Planning rhythm. This is also my second full year of highly detailed Weekly personal metrics saved in a spreadsheet every Sunday afternoon. The end result is a portfolio of artifacts that can be consumed over a cup of coffee that clearly and discretely contain the entirety of my yearly experience.

Like usual, I’m going to resist my nerd urges to just dump a bunch of data from my various personal quantification efforts for the past year (if you care about that, you can see that here). Instead, here’s my best take at a relatively brief narrative review of my 2021 and what I’m looking forward to in 2022.

Phase 1 (January - July): Burnout

I started the year burned out and only got crispier from there. I had been on the same client engagement since early 2019 and was unsuccessful in figuring out a way to keep being jazzed about it. The project itself was radically successful, but I was feeling more and more like an increasingly annoyed fly on the wall rather than an active, optimistic, and effective member of the team. One of the changes I had made late in 2020 was to start a smaller engagement under the umbrella of our larger project. This let me dive into a new part of the organization and operate as a team of one and for a little while it was exciting and engaging. I was laying the ground work with my key stakeholders to hopefully expand the project into something more impactful (and more in my wheelhouse) and all the signals I was getting indicated this was extremely likely to happen. And then, at the end of a meeting at the end of March, my key client, an extremely senior executive, announced he was leaving the company to pursue new opportunities. In an instant, 5 months of hard work flew out the window and with it, the last vestiges of my motivation.

My nearly two and a half year involvement with the project came to a close, with a whimper, in April. I could easily write a whole article about the experience of starting, growing, and ultimately crashing out of this project. 

I knew I needed a substantial break before I started anything new. I didn’t want to quit my job, because I knew my negative feelings toward it were more a function of my extreme burnout than anything else, but it was definitely on the table. Instead of taking that drastic action I decided to investigate what it would look like for The Ready to instantiate a Sabbatical Policy. Assuming we adopted it, my plan was to immediately partake in it.

Luckily, that’s what happened. By the middle of May I had researched, written, and proposed it to the company. By the end of May it has successfully made its way through our participatory governance process and became an official policy of The Ready. I immediately invoked it and scheduled the start of my 4 month sabbatical for the beginning of July.

Phase 2 (July - October): Sabbatical

If Phase 1 was the darkest night, then Phase 2 was the brightest day. I’m somewhat loathe to rehash the entire sabbatical because I don’t think we have the time or space for me to truly do it justice in this article and I happened to do a pretty good job capturing it as it happened.

So, let’s do this montage style. I’ll momentarily drop the coherent narrative and instead flash a few of the key moments across the screen:

• Spending a week in Cape Cod with my fiancee. Seafood for every meal. Kayaking close enough to a seal to say hello.

• Seeing my grandparents in Kentucky for what turned out to be the last time before my Grandpa Bill passed away in October.

• Going to Buffalo (twice!) for family weddings (who knew Buffalo was such a sought after destination locale?)

• Starting salsa lessons with my fiancee.

• Buying a used road bike and exploring the cycling paths in Northern Virginia — which then led me to getting interested in triathlon and starting to work with a coach

• Another trip to Cape Cod, this one shortened by Hurricane Henri

• Working on my brother’s farm in TN for a week. Learning the ins and outs of being a small-scale farmer while experiencing the true misery of August in Tennessee.

• Getting Lasik eye surgery after nearly three decades of wearing glasses and contacts

• Spending a long weekend in rural Pennsylvania with all four of my younger brothers for our second annual Brothers’ Weekend

In between these highlights was a ton of time spent reading and not thinking about work at all (at least at first). However, as the sabbatical started to wind down I noticed myself feeling excited to dive back into work. The feelings that always led me to describe my work at The Ready as my dream job started to re-emerge and by the time I went to sleep for the last time as a man on sabbatical, I couldn’t wait for morning to come so I could rejoin my colleagues in changing how the world works.

Phase 3: Re-Entry (November & December)

Phase 3, which I’m still decidedly in the midst of, was all about re-entering the world of work. In my first two weeks back I had lined up three workshops (one of which was in California) and an advisory project, so I was immediately thrown back into the deep end. Luckily, I still remembered how to do this whole consultant thing. In my third week back The Ready finally had its first in-person retreat since the beginning of the pandemic. For the first time in well over a year I was finally getting to see my colleagues face-to-face; many of them for the very first time! 

At the retreat we decided to kick off an initiative all about figuring out what is going on with web3 and Decentralized Autonomous Organizations. My colleagues kindly nominated me to co-steward that initiative and that’s what I’ve been doing ever since. I’m spending the vast majority of my time every day learning about this emerging space and figuring out how The Ready can best contribute to it. It’s incredibly fun, incredibly challenging, and the perfect thing for me to be working on after 6 years of pretty exhausting client-facing work. I’m excited that The Ready is exploring non-consulting ways to achieve our purpose and it has been a lot of fun to be on the leading edge of that. 

Thinking About 2022 and Beyond

As I mentioned before, I do my big reflection and planning sessions every four months. I really love that cadence but it does kind of make the third trimester of every year a little awkward. I’m not due for a big think on my goals, projects, and other endeavors until the end of February. However, there’s something about the end of the calendar year that makes it feel like a natural time to do a bit of pausing and reflecting. I’m not big on detailed plans anyway, so here’s a few things I’m looking forward to in 2022.

I’m getting married to my best friend at the end of May in beautiful Naples, Florida. Hopefully the COVID situation lets up before then so we can have an amazing time celebrating with our friends and family. Later in the summer we’ll be having a celebration in Michigan for those members of my family who can’t make the trek to Florida. In September we hope to take a honeymoon in Europe that concludes with Emily’s brother’s wedding in Spain.

As I mentioned above, during my sabbatical I got curious about training for triathlons and have been working with a coach and training consistently since the end of August. I’ve signed up for my first three triathlons in 2022. In April I’ll be doing a sprint triathlon, in June I’ll be doing an Olympic distance triathlon, and in early September I’ll be going for a half-Ironman distance triathlon. I’ve found a lot of joy in pushing myself to get better across these three sports and I can’t wait to test myself in a race environment.

Finally, I intend to consume far more art than I ever have before in 2022. I’ve read almost nothing except non-fiction since I graduated from college in 2009. I ramped up my consumption of non-fiction material even more when I started graduate school in 2011 and even higher once again when I started working at The Ready in 2015. Every time I’ve put myself in a situation where I’m not sure if I can handle the workload or felt like I didn’t have the experience I needed to be able to hack it, I turned to books and my ability to read and learn quickly to save me. It has worked pretty well to this point. But I think I’m ready to take my foot off the gas a little bit. I’ve let the part of me that loves stories and games and art atrophy too much. I don’t know what exactly I’m going to do to honor this intention other than reading more fiction, but it’s a challenge I’m excited to figure out.

The Ready exists to change how the world works — to realize a more adaptive, equitable, meaningful, and human way of working. This has meant partnering with some of the world’s largest and most well-known organizations as they strive to remove decades of organizational debt to become better versions of themselves. It has also meant partnering with many smaller and lesser-known organizations who want to develop organizational operating systems that help them retain their nimbleness even as they scale. Not content to swoop in with broad proclamations or sexy PowerPoint slides, we’ve been working side-by-side with courageous leaders and teams who want to actually try new ways of working and are willing to get uncomfortable doing so.

Six years later we’re striving to keep our noses and brains firmly planted to the edge of the future of work. It’s important that we don’t grow complacent in the face of the success we’ve had so far. We work with too many clients who are on the downslope of influence and success after losing sight of the future. What might be next for us? Where are our blind spots? Where are the interesting things happening in the future of work that we aren’t involved with, or even necessarily understand, yet?

It’s impossible to be a future of work thinker and organizational practitioner without hearing about “web3” and “DAOs” over the past few months. As a company, we decided that we needed to get smart about this movement — and fast. It would be a complete dereliction of duty to ourselves, our current clients, and our future clients if we didn’t work hard to understand what’s happening in the world of web3. So, that’s what we’re doing.

Specifically, a colleague and I have committed to spending the vast majority of our time learning about, joining, and contributing to DAOs. The only way to have an informed point of view of this space is to participate. Behind this participation are a handful of foundational questions that we as a company who cares deeply about making the world a better place need to have conviction about:

• Are DAOs and web3 here to stay? Are we just dancing on the edge of an ephemeral bubble or is this the frontier of something important?

• To what extent do DAOs offer a framework for more equitable, adaptive, and human ways of working?

• Assuming every DAOs is not inherently positive in every circumstance, how can we encourage them to evolve in better ways? What role can a company with our values have in making sure the next system doesn’t simply recreate the worst parts of the current system?

• What aspects of self-management and new ways of working are DAOs unnecessarily re-creating from scratch? What roadblocks can we help them steer around as experienced practitioners who have been wrestling with many of these same ideas for a long time?

• What can we learn from what current DAOs are doing and trying that is actually useful to bring to our more traditional organization clients? What bidirectional learning between the “old world” and the “new world” can we facilitate?

• How can we help DAOs get better at all the messy “human stuff” that cannot be abstracted away by technological innovations and always emerges when human beings come together to solve problems (whether there’s a blockchain involved or not)?

• What do we need to understand about web3 and DAOs in order to help legacy organizations effectively bridge their current reality into one where DAOs and other blockchain-enabled approaches become a larger part of their internal and external ecosystems? What do we need to know to advocate for this when it makes sense and to caution against it when it doesn’t make sense?

I’m sure I’ll look at this list of questions six years from now and shake my head at the naïveté of some of them while simultaneously being impressed with how prescient some of them ended up being (it’s definitely something I’ve done before). Either way, the only way you become fortunate enough to look back at your previous work and cringe is by taking the first step to actually put it out there right now.

Perhaps even more important than articulating what we need to do to start figuring out this world is articulating a few things that we don’t need to do. We don’t need to swoop into an ecosystem that has existed for years and act like it’s brand new. We don’t need to bust in the front door and start offering a bunch of advice and platitudes about how things should or could be different than they are right now. We don’t need to come in and immediately impose our own view of the world, as enlightened as we like to think it is, into a context where others have been doing a lot of hard work for a long time.

Instead, we are trying to do a few things:

First is to simply learn as quickly and as deeply as possible. Web3 is notoriously difficult to grok for the non-technical and onboarding practically, and conceptually, requires serious effort. This has been my work over the past few weeks. Reading everything, watching everything, joining Twitter Spaces, watching videos, lurking in Discords, taking notes and thinking thinking thinking.

The trick, especially for someone like me who truly enjoys the solitude and individual experience of learning on my own, is to not get stuck in this posture. I will never feel like I learn or understand “enough.” There is always more to learn and if I wait for perfect understanding I will never move beyond the lurking and learning stage. Instead, I’m trying to remain in a learning posture while also engaging in small ways with the movement I’m learning about. It’s about making small connections between what I’m seeing in web3 and what I’ve learned and experienced as a progressive organizational practitioner over the past six years. It’s replying to Tweets, it’s writing my own threads trying to articulate things I’m noticing, and it’s about asking more questions than making declarative statements about how things are.

Next, and I hope to gradually transition to this phase soon, is identifying specific pain points and tensions in DAOs where I’ve cultivated relationships and offer my expertise in service of solving those challenges. In some cases I think the things we do with our current clients will translate extremely well to DAOs. In other cases, I think we will need to innovate new tools, practices, and processes that are truly custom designed for the unique DAO context. We will inevitably co-create these with other folks — probably many we haven’t met yet — who are bringing shared values and principles to this work, too.

After that the future gets increasingly murky. How does our work with DAOs and the people who do that work at The Ready interface with the rest of our organization? Should The Ready itself create a DAO that brings together progressive org designers and other practitioners? How can we do what we’ve done in the world of regular organizations with DAOs? Murky, murky, murky — but exciting.

For now, it’s back to listening, learning, provoking, and looking for opportunities of helpfulness. Let’s change how the world — and DAOs — work. Let’s make them the most adaptive, equitable, meaningful, and human they can possibly be and not unnecessarily carry over the assumptions, practices, and ways of working that have made traditional organizations so detrimental to so many people.

This article originally appeared on The Ready’s Mirror publication.

Most years (2017, 2018, 2019) I like to take a look back at the tools I found myself using and reflect on the extent to which I’m satisfied with them. While it’s certainly a good practice to be deliberate with the tools I choose to learn and use, this is also my attempt to get my tool stack feeling as solid as possible before heading into the next year so I don’t waste my time fiddling with it later.

A few general thoughts, before diving into a more detailed breakdown:

As I mentioned a few weeks ago, I’ve been leaning into not replacing my core technology as frequently as I have in the past. That means I successfully made it through the most dangerous time of the year for an Apple fan, the fall product releases, without replacing anything in my setup. To be clear, I’m not exactly using ancient gear here (M1 MacBook Air, iPhone 12 Pro Plus, Apple Watch Series 6) but I’m not the absolute bleeding edge, either. That feels right for where I am in my life right now. My hardware is not a bottleneck in my productivity in any way and while it’s fun to have the latest and greatest, I’d rather focus on the work I can accomplish with the tools rather than the tools themselves.

I gave away my iPad Pro to a family member early in the year and haven’t replaced it. That’s partly because Apple hasn’t released a new iPad Pro that felt like enough of an update to justify buying it. At this point, if I’m going to get a new iPad Pro I should probably just wait for whatever the new one will be. Considering my overall trajectory of reducing  and simplifying my hardware stack wherever possible, do I even need an iPad? The past year is telling me that I obviously don’t. We’ll see…

With those preliminary thoughts out of the way, let’s dive into an area by area breakdown of what I’m using and how I’m feeling about it.

Hardware

• Apple wireless keyboard & mouse (old)

• Kindle Oasis (2018)

• HPZ 27” External Monitor (2019)

• Logitech Webcam (2019) & Blue Yeti mic on a boom (2019)

• AirPods Pro (2019)

• M1 MacBook Air (2020)

• Apple Watch Series 6 Cellular (2020)

• AirPods Max (2020)

• iPhone 12 Pro Plus (2021)

Nothing about this needs to change in 2022. I hope nothing breaks and I can just go through the entirety of next year with this exact setup.

Browser

Most of the year, as it has been basically every year I’ve done this, my browser across all devices has been Safari. It’s hard to beat Safari for integration with the operating system, privacy, and overall speed. Sure, every once in a while I hit some sort of weird wrinkle on a website and need to fire up my backup installation of Chrome, but 99% of the time Safari is what I reach for to surf the web. That is, however, until the past couple weeks.

Recently my work has taken me into the world of crypto and one of the first things I learned is that Safari couldn’t be my daily driver and also my default crypto browser. So, it looks like I’m going to be splitting time between Chrome on macOS and Safari on iOS (for now). I’ll probably end up trying Chrome as my default on iOS sometime soon, just to see if having it be the same everywhere is worth it.

Previous Years

• 2017: Safari

• 2018: Safari

• 2019: Safari

Music

Spotify and Apple Music have been locked in a pretty even battle for my attention for the entirety of the time they’ve co-existed. I’d go for a few months using Apple Music (whose design and UX I tend to prefer) and then I’d switch to Spotify (whose recommendations are far better). This year, for the first time in a long time, I’ve been almost entirely in the Spotify camp. A major sign that things have gotten more stable with my Spotify usage is that I find myself looking forward to the Discover Weekly playlist update every Monday. I think Spotify is likely here to stay.

Previous Years

• 2017: Apple Music/Spotify

• 2018: Apple Music

• 2019: Spotify

Podcasts

I’ve been all in on Overcast basically since the day it came out. I’m a huge fan of its simplicity and reliability. It hasn’t gotten any sort of visual refresh in a long time, but I honestly haven’t been bothered by that. My goal is to interact with my podcast player as little as possible; so long as the UX doesn’t get in the way of that goal, I’m happy.

Previous Years

• 2017: Not recorded, but probably Overcast

• 2018: Overcast

• 2019: Overcast

Email

This year saw the biggest change to my email that I’ve had in a long time. After successfully avoiding the Superhuman hype for a long time, I eventually caved and tried it out. Turns out it’s really, really good. Would I use it if my work wasn’t paying for its painful $30/month subscription? Probably not. But if someone else is willing to pick up the tab then I’ll happily use it. It’s fast. It’s clean. It’s simple. It’s everything I want in an email app, really.

Previous Years

• 2017: Apple Mail/Airmail

• 2018: Airmail

• 2019: Airmail

Notes & Writing

It’s another year of Bear and Ulysses serving the majority of my writing needs. Most of my writing starts in Bear. It holds ephemeral notes that I need for just a short period of time, notes related to active projects that tend to live for weeks or months at a time, and it’s even the starting point for longer form writing. Once I’m ready to turn something into a piece of longform writing (like this article), I’ll move it over to Ulysses and finish it there. This writing duo has been solid for the past three years and I’m more or less happy with it.

New to the group this year, though, is Obsidian. After struggling with the concept of “digital gardens” and “Zettelkasten” I decided to really experiment with setting up one of my own. I think it’s still a bit of an open question whether it becomes a crucial part of my writing process, but for now my nascent Zettelkasten system is living in Obsidian.

Previous Years

• 2017: Bear/Byword

• 2018: Bear/Ulysses

• 2019: Bear/Ulysses

Read Later & RSS

This is another part of my software stack where I pretty consistently get a bit of a wandering eye but almost always end up back where I start, Instapaper. That didn’t really change this year. I went through a phase of using Apple’s integrated Reading List (again) and even poked around Pocket (again), but ultimately I came back to Instapaper. Something about its limited feature set, simplicity, and how well it handles me throwing things at it from lots of different places has made it a really solid part of my workflow. This year I started playing with Readwise and it has helped make my Instapaper archive an even more helpful place as it surfaces old notes and highlights.

RSS-wise, I’m happy with my Feedly/Unread combination that has been pretty solid for the past few years. Unread feels really snappy and  has an awesome feature where double tapping an article automatically saves it to Instapaper.

Previous Years

• 2017: Instapaper & Reeder

• 2018: Instapaper & Feed Wrangler/Unread

• 2019: Instapaper & Feedly/Unread

Calendar

I’ve become a much bigger proponent of hyper-scheduling/time blocking as a productivity practice so I’ve been leaning on my calendar software much harder than I have in the past. Luckily, Fantastical is a truly stellar piece of software. I love having different sets of calendars I can hide/show with the click of a button because I tend to work with different colleagues on several teams at once. Being able to see our different calendar configurations very quickly is amazing.

There’s a cool new kid on the block, Cron, that is trying to be the Superhuman for calendaring. I’ve played with it a little bit… and it is pretty good, so I’ll be keeping an eye on its development over the next year.

Previous Years

• 2017: Fantastical

• 2018: Fantastical

• 2019: Fantastical

Things

Not much to say here. Things remains the bedrock of my task management system. A rock solid piece of delightful software. Considering how frequently I use it you’d assume I’d have found and been annoyed by all its rough corners. That’s the thing, though — it doesn’t have rough corners.

The only frustration  I have with it, and it’s not even really a problem with the software, is that I occasionally work on projects with colleagues where we’re using a shared Kanban board in Trello or Notion as a project management tool. In those cases I end up basically manually syncing my Things database with those tools, which can be annoying and error prone, but it’s not the end of the world.

Previous Years

• 2017: Things

• 2018: Things

• 2019: Things

Books

I’ve always felt weird and bad that I’ve basically split my electronic library across two incompatible services: Apple Books and the Amazon Kindle. This year, I decided I’m going to default to buying my books from the Amazon Kindle ecosystem so that I always have the option of using a Kindle to consume them. I don’t mind reading on my phone, and in fact read almost the entirety of War and Peace on it this year, but every once in a while it’s nice to use a purely dedicated device for reading. If I want to do that, I need to buy my books from Amazon. So, that’s what I’m (mostly) doing.

Previous Years

• 2017: Apple Books/Kindle

• 2018: Apple Books/Kindle

• 2019: Apple Books/Kindle

Stuff That Hasn’t Changed Much Recently But I Still Use and Enjoy

I don’t have much to say about these other smaller utilities other than many of these have become solid contributors to my overall tool stack. Everything in this list has been the same for at least the last two or three years.

• Weather: Carrot

• Habit Tracking: Streaks

• Password Management: 1Password

• Maps: Apple Maps

• Journaling: Day One

• Sleep Tracking: AutoSleep

• Delivery Tracking: Deliveries

• Movie & TV Tracking: Letterboxd & TV Time

• Calculator: PCalc

• Flight Tracking: Flighty

• Life & Administrative Management: Notion

• Reddit: Apollo

• Time Sensitive Reminders: Due

• Recipes: Paprika

• Video Calls: Zoom

• Work Chat: Slack (with Discord becoming a larger part of my life now)

• Work Task Management: Trello & Notion

• Fitness Tracking: Strava

• Online Backup: Backblaze

• Social Media: Instagram, Twitter, & LinkedIn

• Audiobooks: Audible

• Newsletter Publishing: Substack (moved away from Mailchimp this year)

• Personal Website: Squarespace (articles syndicated to Medium as well)

Stuff I’ve Stopped Using

And on the other side of that coin is the stuff that I’ve stopped using. Sometimes it’s because I’ve found a tool that does something better than what’s on this list and sometimes it’s because whatever job this tool was filling is no longer something I need done. Many of these are great and worth checking out!

• Tweetbot

• GoodNotes (without an iPad I haven’t had much need for it)

• AnyList & Grocery (just use a shared Reminders list for groceries now)

• Timery (my calendar has basically become my time log)

• Nomorobo (spam calling seems better blocked by the OS nowadays)

• Calm & Waking Up (not really focusing on meditation at the moment)

• Bobby (no longer needed)

• 1Blocker

• UpHabit

• Stoop Inbox

2022 and Beyond

As with everything in my life, I’m always looking for ways to simplify. One way of simplifying is to avoid using specialized apps wherever I can and learn to get by with the default apps Apple provides as much as possible. I’ve run that experiment many times, and I’m sure I’ll have some moments over the next 12 months where I’m feeling overwhelmed and wanting to take drastic action in that direction, but I’m going to do my best to avoid any new Default Apps Only experiments. They tend to be quite disruptive to my workflow and they never stick for longer than a week or two.

Instead, I’m going to be on the lookout for ways to either a.) learn my current tools better so they become even more seamless and simple to use and/or b.) look for workflows that I no longer need or want in my life — meaning I can jettison the tools associated with that workflow. I already run pretty lean, so I don’t think it’s super likely that’s a path I’ll be exploring much in the next year, but it’s always possible.

Honestly, the best thing I can probably do for my sanity, productivity, and minimalist desires is to completely forget about everything on this list until I sit down 12 months from now and write my retrospective on 2022!

I’d love to hear about the tools you use and love. Let me know on Twitter or by shooting me an email.