2022 State of the Sam

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.

A typical shot of my home office in 2022.

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.

Dinner in NYC for another The Ready company retreat. Also, tiny little shorts.

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.

Full company retreat in Miami.

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 should probably use a more dignified picture of our wedding, but I think this one sums up the true vibe the best.

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.

Third annual Spurlin Brothers weekend in Columbus, OH.

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.

Getting ready to ride my bike, but really just happy to no longer be swimming.

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.

State of the Software in 2022: A Review of the Tools I Use to Live and Work

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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Making Deliberate Decisions about the Evolution of My Career: A Seven Year Retrospective and Looking Ahead to What's Next

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.

An Experiment in Focus, Space, and Making Progress on Something Difficult

Today, Friday, July 8th, I’m commencing a four-week experiment centered on the need to make progress on an important project. In what I’m hoping isn’t a too egregious case of cultural appropriation, I’m calling it Monk Mode.

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.

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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.

A Race Report From My First Triathlon

Near the tail end of my sabbatical during the summer of 2021 I decided to explore getting into triathlons. It had always been something bouncing around the back of my head, but for various reasons had never really taken the plunge in a meaningful way. One used road bike and a gym-with-a-pool membership later, I was on the path to my first triathlon. Now, roughly seven months of extremely consistent training, I’m looking back at actually completing my first one.

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.

I never properly mourned the end of my hockey career

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.

Stop trying to change your habits and start playing with Deliberate Patterns instead

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!

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DAOs and Their Evolving Operating Systems

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.

The OS Canvas

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?

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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.

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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.