(You may be interested in last year's annual review.)

Health

I wrote last year:

I am, as I write this, in the best shape of my life

In retrospect, this was:

• a hilarious way to start an essay
• true, and no longer so.

I committed to hitting the 1/2/3/4 club this year, which I accomplished (yay!), but shortly thereafter I fell into what I would describe as a pleasant fitness malaise: my only real goal was improving at bouldering, which I didn't quite commit myself to enough to hit my resolution of sending a V6 route. As such, I mostly spent the year in maintenance mode: jogging, lifting, climbing, and staying active, albeit not quite as much as I should have.

The past two months have been better! I picked back up a lifting routine that, while brutal, has always been effected (nSuns, for those curious) and have been more nutritionally conscious than usual (we're generally pretty good about eating healthy in the house, though there were a few too many cocktails and burgers than there probably should have been.) ^[1]

Beyond that: no news is good news.

Family

Haley and I got married! It was the best day of my life.

I think almost everything that can be said about weddings has already been said ^[2], but a thing that you can only appreciate while it's happening is just that one possible version of a wedding — our version of a wedding — is spending a full day with your favorite people in the entire world in a very beautiful place, and while such a description always made a certain level of abstract sense to me I don't think it quite hits you, really hits you, until you realize it is suddenly six p.m. and everyone who you care about in life is in the same room as you, well-dressed and flush-faced.

The only absent member of the family at our nuptials was, of course, Telemachus, who spent the weekend at a farm with his brothers and sisters. I feel as though I have run out of ways to describe Telly: he is a perfect dog, strange and soft, filled with the kind of love and loyalty only canines can provide.

Being married is not particularly different than being engaged; I wake up every morning and go to bed every evening next to my best friend and favorite person in the world. I get to it now with a ring on my finger; all I hope for is to never be so dumb as to take it — even for an instant! — for granted.

Buttondown

There's a slightly more self-serving version of this on the official Buttondown blog but — man, what a year.

Buttondown's functionality doubled and the core experience got even stronger; I hired part-time writers, engineers, and support staff to scale out its growth; it suffered fewer bouts of downtime or serious incidents than the year prior; every single financial metric improved.

The users of Buttondown now include columnists at the Washington Post, New York Times, and The Atlantic; winners of the Hugo, of the Pulitzer, of the Apple Design Award; bloggers I've read for decades; maintainers of Open Source Software used by millions; publishers whose games I've played for hundreds of hours; poets, artists, high schoolers, jazz troupes; Ivy League departments and Mutual Aid organizations; skeeball, pickleball, and bouldering leagues.

It has officially grown beyond my wildest dreams, and done so while hitting a 99.8% CSAT score.

More than that, it remains a business of which I can carry a high level of moral pride; it is a reflection of my ideals about what software can do and how a business can be run.

All of which either underlines or belies a larger point: this is easily the hardest I've worked in my professional life. I am grateful that all of this hard work is for a project I care so deeply about, and for a project whose users find it so valuable.

My goal entering this year was an amorphous thing that I had informally referred to as "Buttondown 2.0":

In 2023, I want to — need to — transition my relationship with Buttondown from that of a successful project to a stable, growing, mature business.

Mission accomplished.

The question that the industry trains us to ask is: what's next? I think that's obvious from a product perspective but a little less so from an organizational or business one: but my high-level goal for next year is to make a full-time hire, and all of the financial/existential commitments entailed therein.

Third South Capital

My friends and I started a holding company. We purchased five businesses, and it's gone pretty well; they've all grown, and we're going to make another purchase or two next year.

Our goal with this first year was, more than anything else, to accept or reject the null hypothesis: regardless of financial return, was this a fun and interesting way for us to spend our limited time and energy? The answer has been yes. The three of us all have different backgrounds and are all getting different things out of it: for me, I'm loving the intellectual exercise of being able to evaluate and implement strategies on businesses with which I have slightly less emotional attachment. ^[3]

I haven't written or posted too much about this experience (in no small part because it's not just my experience to share!) but it has been much more rewarding than I expected, and expect more writing on this front in 2024.

Writing

I wrote 22,000 words in a personal blogging capacity last year; I know not what that number was for 2023, but I am very confident it was much less. I am very proud of my more serious essay-writing over at Applied Cartography, even if it was few and far between. (And arcana.computer remains alive, albeit in stasis — I'm still keeping my media journals updated, but MDX is now so slow at processing my thousands of files that builds are broken. I will try to fix this in 2024, though I'm not quite sure what form a "fix" will take.)

Media

My reading this year was fairly flat (34 books, compared to 32 last year); my gaming was down (5 games, compared to 7 last year); my films were way up (53, compared to 25 last year!). Some favorites across the entire spectrum:

• The Conversation and The Green Knight were two sensational films that belong in everyone's canon;
• Baldur's Gate 3 is just as good as everyone says it is (and I say that despite having not finished it!); 13 Sentinels: Aegis Rim is a triumph of postmodernism.
• I was very close to having not read a single book that I truly loved this year until I finished up — only last week — The Name of the Rose, which is now one of my favorite ten books of all time, and one whose many messages and ideas will be roiling around in my head and heart for many years to come.

Miscellany

• I spent two thirds of the year ending every evening by spending fifteen minutes on some quantified self work: where I spent my time, how many drinks I had, how much caffeine I had, etc., with a goal of making sure I wasn’t going to burn myself out or otherwise ruin my health. I think I gleaned some amount of insight from this (I realized that I was not spending enough time on non-Buttondown things; I caught myself when I was drinking on more weekdays than I wanted to) but I abruptly stopped this practice in September and am no worse for the wear.
• Feels deeply weird to, for the first time in ~ten years or so of doing this, not have a section dedicated to some external employer.
• I find my relationship with social media in a generally good-but-frustrating place. The town square of Twitter has been replaced with six different fora that I need to keep tabs on — bsky, Discord, LinkedIn, Signal, Mastodon, Twitter — and the sheer frustration of doing so has resulted in me spending less time in consumptive mode.
• I find myself missing not just a town square but a water cooler. I am grateful to my friends Sumana and Harrison for providing some palliative care in this nature: having coworking and mastermind sessions to break up the week and connect with others is extremely gratifying.
• No new projects; I don't foresee any others in the coming year as well (much to my chagrin).
• Emojis on the rise in 2023: 🫡, 🐬, 🍳.
• Emojis on the decline in 2023: 😎, 🙏, 😅.
• This was our first full year living in Richmond, and while we didn't spend as much time exploring it and becoming more entrenched in the culture as we would have liked (this is perhaps reasonable, given the aforementioned wedding and honeymoon and general sense of happy chaos that permeated the year) we love it more than ever. We've found our neighborhood bar, we've found (and lost) our favorite restaurant and cidery, we've re-found a favorite restaurant, we re-finished our backyard and in general have done a lot of fun stuff. It is a great privilege to have a home you love.

Resolutions

• Bench three plates.
• Publish twenty essays.
• Open-source four major components of Buttondown.
• Remodel my garage.

Coda

For the past few weeks I've been mulling over an essay with the working title of Something's Gotta Give, and indeed that feels like the main lesson I learned this year. I wrote last year that I felt like I was entering 2023 with a clarity of purpose that had been lacking in my professional life for some time; that clarity has given way to lots of great work, many happy memories, and a sidelining of things whose importance or urgency feels marginal.

The median day of 2023 looked something like this: eight hours of sleep, a good workout, ten hours of exhausting intellectual work growing a business, some puttering around the house and tending the garden, two dog walks, an evening spent unwinding with my wife, an episode of anime with my brother. There are a lot of things I wish I could fit into that day: more time writing, more time exploring new technologies, more time playing video games, more time exploring Richmond. At the same time: I think I chose wisely.

2024 purports to be much of the same. If there's any change I could make, it'd be making sure that some of that more passive time — the sixty quiet minutes on the couch after dinner, the thirty minutes between lunch and an afternoon meeting — is spent more mindfully, as opposed to picking up a random round of Brotato and/or brainlessly refreshing analytics.

Thank you

To: my wife, Haley, the light of my life; to everyone who attended our wedding; to my parents and my brother, for too many reasons to enumerate; to Harrison and Colin, the best business partners a guy could ask for (and for five lovely and earnest counterparties who entrusted us with their businesses); to everyone who became a Buttondown customer this year (or reported a bug, or referred a user, or pushed code); to the hodgepodge of former coworkers, emoji-filled Discords and group-chat emigres whom I consider a water cooler in lieu of an employer-sponsored Slack; to Jimmy Butler and Zach Lowe; to you, dear reader, for getting this far.