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


I wrote last year:

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

In retrospect, this was:

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.


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.


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.


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.)


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:




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.

  1. On the cocktail front: this is the first year where it's been aggressively obvious how much a single drink will hit my energy for the following day or two. I know teetotaling is a bit of a meme at the moment (and it's certainly not something I'm advocating for), but I've had to really budget my energy with the knowledge that a happy hour or a late dinner with drinks means I won't be nearly as close to 100% the following day. ↩︎

  2. Though keen readers of my writing would quickly note that such a fact has never stopped me from bloviating anyway! ↩︎

  3. Buttondown is, more than anything else, my baby: there are tons of "correct business decisions" that I could make with Buttondown that I refuse to out of emotional attachment. ↩︎

Lightning bolt
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