Number of times I’ve texted “gahhhh sorry for the late response”
Hours spent gaming with partner
Photos of Telly taken whilst he sleeps
Bottles of Veuve Clicquot consumed


I ended 2020 in a period of what could generously be called “fitness stasis”; I was working out and walking but not particularly pushing myself in any direction. In retrospect, too, I was drinking a lot more than I should have: it was a stressful Q4 for Haley and myself, work-wise, and a friend bequeathing us a solid two gallons of egg-nog did not help matters.

Things went better this year! I got on a solid lifting program ( SBS 2.0, and then back to my old mainstay nSuns once I got back into the rhythm of five-a-week lifting), ran a couple 5Ks, and in general we’ve been eating better. My lifting peak was in late 2018, and I’m more or less back where I was back then: close-to-but-not-quite-at the 1/2/3/4 plate club.

In 2022, I want to hit the 1/2/3/4 plate club. (The 1/2/3/4 plate club, if you're unfamiliar, is a one-plate press (135 pounds), a two-plate bench (225 pounds), a three-plate squat (315 pounds), and a four-plate deadlift (405 pounds.) This is not a particularly aggressive achievement: I’m sitting at a 130 OHP, 215 Bench, 245 Squat, and 335 DL, so it’s mostly about getting my squat numbers up. But this was a fitness goal that, when I started lifting six or so years ago, seemed like an impossible horizon, and now it feels…very much possible, with dedication!


We got Telemachus in September of 2020; he’s around a year and half years old now. He still has lots of puppish tendencies: every new stranger is a thing of joy, and every scary noise is a thing of terror. But he’s started to become more of a capital-d Dog: while he’s still energetic, it’s less of a “we need to walk him three miles a day or else he is a terror” situation and more of a “if we walk him two miles in the morning he is more or less out of commission” situation.

This time last year, we were very proud of him/us for removing the play-pen/prison from our living room & office so he could move around the house unencumbered. How quaint that seems now! The dog is our shadow, and he like us is a creature of habit: he curls up with us in bed (a particularly cute habit of his: he’ll jump down to his kennel as we turn out the lights and, around fifteen minutes before sunrise, jumps back into bed and snuggles with Haley), keeps guard from his roost atop the couch, and is the greatest office dog we could ask for.

He is not perfect, of course. His playfulness manifests as rebellion, and I’ve had more than a few mornings interrupted because he sprinted out of the house chasing a mailman; our backyard needs to be resodded from two digging sprees (and, to be fair, because my deadlifts left pairs of heavy divots). We call him The Goblin (a term of affection, I promise), and perhaps a more accurate moniker would be Puck; he is a prankster, a mirth-font, a lumpen bag of tricks and joys.

I have run out of laudits for the dog: he is the light of our life.

(Also, I bought


I got engaged! :)

I surprised Haley when she came back from a trip to Virginia and a subsequent dinner with her family; she opened up the door to our house (whilst wearing sweats, much to her continued chagrin) to me wearing a suit and carrying a dozen roses, with candles and petals strewn across the living room. I had a bottle of Veuve Clicquot in the fridge; I had a large pizza in the oven. I told her I loved her very, very much and wanted to spend the rest of my life loving her very, very much and then some other stuff that I frankly cannot remember because it was rather emotional. She said yes.

I honestly do not know what else to write here. I have my soulmate. We spent all of four days apart this year and they all sucked. I am very, very lucky, and to write more would be trite.

More date nights and lazy mornings, of which there can never be enough.


Some other updates that don’t quite warrant their own section:

  • We’re moving back to Virginia! I love Seattle with all of my heart, and will be very very sad to leave, but the timing was right: Haley’s sister just had a baby, we found a great house in Richmond, my team is permanently remote, and the Seattle housing market is fairly bonkers. (If you’re reading this and live in Seattle — let’s grab a coffee/beer/sashimi! Or not. I’ll be coming back fairly often.)
  • After spending a nice amount of time revamping my personal website (! You’re on it! And there are a bunch of links in this very web page to it!) I spent almost no time writing or improving it. Which is fine — that is not important, in the grand scheme of things. But I am increasingly enamored with the idea of using it as an outlet, and I’d like to spend more time working on it and tinkering with it. I am coupling the act of “writing” and “tinkering with my site” intentionally here — both of them are done more for self-gratification and self-discovery than anything else (I am no longer at the point in my life where anything can seriously change from becoming known more as a blogger.)
  • This is not particularly virtuous in of itself, but I’ve done a particularly good job in terms of sticking to a schedule and being “productive”. This was a big goal of mine this year after the chaos of 2020; investing a lot in personal systems helped me survive during this particularly tumultuous year.
  • I got absolutely no work done on the house. This ended up netting out okay, since, well, we’re leaving the house to go move across the country, but I can’t point to a single project that we spent time on in 2021.
  • I got a bunch of press! I showed up on Daring Fireball (twice) and was interviewed for the Los Angeles Times; chatted about Buttondown on Running in Production and Coding Cat (and did an AMA in /r/SaaS); got to share some cute photos of the double desk on Workspaces; and participated in a hallowed Var Talk in Keep Going.
In 2022, I want to (once again) rebuild Spoiler alert: this is already almost half-done, so counting it as a 2022 goal feels like a bit like cheating. But I want to have a place where I can throw all my thoughts, and I genuinely want an easier way for me to sift through my notes and my books and all of those things, and I want to just have some fun programming it. The whole “stop rebuilding your blog and just blog” thing is so passe — you should spend your time doing whatever brings you the most joy, and if I happen to fart out some essays about management or whatever along the way, then great."


Twitter bio changes logged
Emails sent
Net new MRR
Angry emails received
Production breakages
Arcane DNS issues debugged
Commits made after midnight
DMs received from colleagues about my tweets
Teddy Ruxpin dolls shipped
New products launched


Stripe is a company that builds payment infrastructure. I have been working there for about four years, working on reporting infrastructure. It was a very good choice; I've learned a lot. Come work with me!

I am an engineering manager now!

I haven’t done a lot of soul-searching and reckoning about the transition, and every time I try to write about it my words come out in listicle form. I think if I could whittle things down into the three talking points I've deployed most often, they’d be:

  • The single funniest — and most portentious — moment of being an EM was when I was starting to tell folks that I had made the switch. Every single IC I talked to said congratulations!; every single EM I talked to said good luck!

  • Tripling a team’s size in three months was the single hardest and most rewarding thing I’ve done in the industry. Sourcing and selling are things that you might expect to be relatively solved problems, given their ubiquity and value; they very much are not.

  • People warned me about how hard it is to give up programming & “thinking as an IC” on a day-to-day basis. They are absolutely correct (and, frankly, I wouldn’t have felt comfortable giving it up if I didn’t have Buttondown and other projects to keep that part of my brain sated). The thing that they did not sufficiently warn me about was the mental recomposition required to shift from a proactive lifestyle — where working at a company revolves around the metagame of pursuing maximal deep work on impactful, interesting projects — to a reactive one, where most of the things that happen within a given day are obscured by fog of war until they start to happen.

    But that says nothing about what it’s like to be an EM, nor why I’m grateful for the opportunity, or what I wish I knew (besides the bit about hiring) or anything like that. And that writing is yet to come, I promise!

...Now, that’s a very solipsistic look at Stripe, and I will of course elide most of the interesting details that have to be redacted for reasons. If you’re a fellow Stripe, you might guess that I’m particularly proud of aaaaaaaaaaaaaaaaaa and that I love that we’re finally aaaaaaaaaaaaaaaaaa the aaaaaaaaaaaaaaaaaa.

If you’re not, you can at least trust me on this: I am officially in the jaded phase of my career. My ennui is at an all-time high; I think I understand the zeitgeist pretty well, and very little of it is novel or exciting to me. The panacea to this ennui is my employer: I get to work on a bunch of fairly chunky problems with the nicest, smartest people I’ve ever met to make economies better.

(Also, we’re hiring.)


Buttondown is an application for building, growing, and sending newsletters. I started it in around 2016; it's around $8K MRR and responsible for me knowing too much about DNS infrastructure.

A couple notes on the financials:

  • MRR was of course up YoY, but that belies a different trend: MoM revenue has stalled out over the past few months, for the first time in ~ever. The free lunch of new users from “the creator economy” is stalling out, and I’m ending the year non-trivially south of Buttondown’s peak ($10,105 — that sweet taste of five-digit MRR).
  • My average user is worth more, but is younger (thus the lower LTV) and churnier (thus the higher MoM churn) than ever.
  • Operating costs increased in absolute terms but decreased in margin, thanks to dedicated efforts last quarter.

In non-financial terms, what went well:

  • Honestly, annual planning was a very useful exercise. Every single item in my 2020 retrospective which I completed was absolutely the right choice, and the things that I punted on (improving the conversion funnel, for instance, since in H1 I was deluged by organic traffic) is stuff I want to pick up this year.
  • Buttondown is still growing, and more operationally stable than ever. This time last year I was really at wit’s end with customer support, and there were points of time during this year where I felt ready to declare a certain amount of operational bankruptcy. Things are calmer now: I might not be able to make as much day-to-day progress as I’d like, but I’ve found a very good balance and set up strong structures to make sure that I’m not spending the lion’s share of my time putting out fires.
  • This is very much an engineer’s thing to say, but: Buttondown’s codebase is in the best shape it’s ever been, thanks to piecemeal investments in TypeScript, pytest, Storybook, and a host of other things. I think this is actually pretty important: an enduring tactical advantage I will have over my competitors is agility, and I think I’m entering 2022 with more agility than I entered 2021.

What did not go particularly well:

  • As mentioned in the financials bit: I think the free lunch of everyone suddenly caring about emails again is over. The space is bigger than it was, and it is growing, but the second-order derivative is flat. This makes it newly urgent to focus on making sure that the folks who are trying out Buttondown stick to Buttondown.

  • On a personal note, I fell victim to lapses in discipline throughout the year. Some of this is me being overly harsh on myself (a lot of things happened! I became an EM and tripled my team size! I got engaged! I’m moving! I have a very cute corgi!); some of it is poor planning on my part. There are entire months where I was too lazy to plan out ambitious work and instead settled for bite-sized commits here and there.

  • The two habits I wanted to improve upon this year — more content-writing, and more metrics usage — both fell flat. Whoops!

In 2022, I want to hire a full-time VA! Buttondown will never be 100% operationally trivial, but it's gotten much more so in the past year, and a lot of my day-to-day customer service burden is pretty routine. I've ranted a lot about scaling Buttondown mostly being an exercise in figuring out expedient ways to trade money for time, and this seems like a perfect option there.
Also, a host of smaller things I'm excited to ship for Buttondown in 2022 (though, as always, plans prove fickle):
  • Launch a new pricing plan
  • Add affiliate support for both subscribers and authors
  • Localize the subscriber-facing app
  • Rebuild the app's scaffolding
  • Rebuild the events & analytics engine
  • Rebuild the core settings pages


Spoonbill is an application for tracking social media metadata. I built it in around 2016 and it's more or less been in maintenance mode ever since.

Absolutely nothing happened in Spoonbilland in 2021. I got three more $99/month contracts and did not write a single line of code. Not bad.

(I continue to harbor illusions/dreams about relaunching and rebuilding Spoonbill to be a general-purpose metadata delta tracker, but there is literally not enough time in the day to even plan on such things.)


No new projects, no new engagements, no new consulting — all of which was by design, so mission accomplished there. (The only thing worth calling out, I think, is that I spent another year mentoring for Unloop. If you are a cushy-situated software developer — and if you are reading this, then odds’ are that you are — I can think of few better ways to spend one of your precious few spare hours in a week than finding a worthy program and offering your time as a mentor. It is both deeply gratifying and deeply valuable.)

In 2022, I do want to build something new and bring it to market. I miss the early stages of going from zero to one, and Buttondown is in a better place ops-wise than it’s been in 24 months. I think this will be a very modest project, in terms of ambitions — I’m thinking something along the lines of $50K TAM — but I like the idea of adding to my portfolio and having some fun along the way.


Hours spent listening to lo-fi
New albums
Hours spent playing Slay the Spire
New words learned
Books read
Movies watched
Games finished
Number of times I successfully guessed the murderer in Poirot
Absolutely awful management books read


I read (and listened to — the lion’s share of these were audiobooks, a format that I will continue to rhapsodize about if you corner me at a party) 41 books this year, up a fair bit from last year. This wasn’t particularly deliberate; I think it happened naturally as I phased out most of my podcast consumption in favor of audiobooks.

There was a lot I really liked. I’m finally an Infinite Jest guy (email me with all your wildest theories!); No One Is Talking About This is probably the only good “book about the Internet’ that I’ve read, and I did a much better job reading poetry than I did in 2020 (even if I want to do even more next year; I bought more than I read!)

My favorite book of the year — and my lone 10/10 — was a cliche one, to be honest. Path to Power took me the better part of two months to wade through, but it was absolutely tremendous, and to me a few steps ahead of The Power Broker. I am wary of the need to even provide the summary — I suspect my target audience is all-too-well-aware of Robert Caro’s ouevre — but I don’t think I’ve read a non-fiction book with greater discipline, ambition, or poise. (And I’m excited to continue along with the series, albeit with some breaks along the way.)

One of the more rewarding things about this year is how nice big-ass books have been. I think I have subconsciously shied away from them in favor of the slight endorphin rush of smaller books and the diversity of different voices, but I’ve loved all of the huge books that have been on my list for five-or-so years. They’ve all been worth the investment! With that in mind…

In 2022, I’m going all in on comically large books. Brothers Karamazov; War & Peace; Middlemarch; A Little Life; Means of Ascent; Women & Men.


I wrote last year that more than anything I wanted to finish more video games, and boy did I succeed. I finished a solid 9 games this year, and none of them (besides maybe Gnosia, which was absolutely worth it) were “padding”; they were all sizable, non-trivial games. I would recommend every single one of them except Trials of Mana, which was the height of mediocrity.

I struggled a lot to choose between my two runaway favorites - Disco Elysium and Celeste, both of which were GOTY contenders in their respective years and absolutely, unquestionably, unimpeachably great. A bit of each:

  • Disco Elysium is a choose-your-own-adventure where you play an amnesiac alcoholic cop trying to solve a murder in one of the most fascinating settings of any I’ve ever played. The writing is — this cannot be overstated — the best, as in there is no game with better writing in the world.

  • Celeste is a viciously difficult platformer in which you play as the titular Celeste, a young woman trying to climb a mountain. It is very sweet: the plot of the game is very much about the joy and difficulty in doing hard things, and the vicious difficulty is perfectly balanced with an overwriting sense of fairness; the game does not trick you, the game does not punish you, the game only asks you to be very, very talented.

In the interest of choosing one, I’ll choose Celeste, which besides having - for my money - the best platforming gameplay of all time, was a perfect fable about the challenge and ecstacy of playing video games (I’m a sucker for earnest & optimistic metareference!). That being said… absolutely play Disco Elysium. (And Bastion, and Gnosia, and Steamworld: Quest, and probably Cave Story, and I haven’t finished it yet at the time of this writing but definitely Shin Megami Tensei V too.)


If I succeeded beyond my wildest dreams in playing games, I did a much worse job of watching movies: only fifteen this year. Bluntly, I didn’t find any of them brilliant! The two movies I rated the most highly at the time were Ponyo and Holiday, both of which were slightly shallower echoes of all-timers for me (My Neighbor Totoro and Bringing up Baby respectively). Beyond that, I have to tip my hat to In A Lonely Place , my birthday movie (I watch a new Bogart every year), which was certainly not a pleasant film but a quiet and beautiful one) and Promare, a balls-to-the-wall kaleidoscope of pastel animation with a cliche-but-not-grating plot that mostly acts as a minecar to take you from one delightful setpiece to another.

In 2022, I want to watch 50 films. I don’t like quantitative approaches to consumption — you run the risk of doing the thing to say you did the thing, not doing the thing because you want to do the thing. But I miss movie nights with Haley and getting to spend time in worlds outside my own; I can point to very few movies that I regretted spending time with (which is absolutely not true of books, games, and television) and while habits aren’t virtuous in of themselves I think the lack of movies in my life this year was not due to distaste but due to muscle atrophy.


Last year I watched roughly no new television. This year I did much more, clocking in at a final 21 seasons of television! This mostly came from two different places:

  1. Haley and my watch-something-during-dinner gambit evolved from completely smooth-brained television (Frasier, Degrassi) to stuff we actually were interested in watching.
  2. My brother and I started watching a whole lot of anime together.

The second bullet point is where my favorites of the year lied; we started off with a classic (Serial Experiments Lain, which was terrific in its own way but not my absolute favorite) and then bopped around some more modern hits. Oddtaxi (and The Tatami Galaxy close behind it) were triumphs of the form: a show that could have only been told in animation, delightful in a visual form, and being deeply resonant and fun in their own rights.

(Also, shout out to Netflix for putting out some of the absolute worst content I have consumed this year, though Emily in Paris and Friends from College quickly earned value for hitting that negative underflow of “so-bad-you-can’t-look-away”.)


Last year I listened to roughly no new music. Much like with television, I made up for it this year, clocking in at 119 albums in total. That’s around two a week, which sounds about right: I didn’t have any grand methodology or framework, just idly browsed Pitchfork and jotted down notes whenever someone mentioned something that sounded interesting.

I listened to a lot of music that I loved, to be honest: five albums that I gave the very scientific and vaunted personal rating of 10/10. If I had to choose one, I would choose based on just how many damn times I listened to the thing, which would be Charmed by DJ Sabrina the Teenage DJ (I know. The name is bad. I know. But trust me — it’s fun, and a solid two and a half hours of sample-heavy boppy house) followed by Leave the Bones by Lakou Mizik & Joseph Ray (a modernist recording of Haitian tribal pop that recalls the epic highs of the early eighties world trend.)

Coda / 2022

As you have probably realized, rather than saving all of my goals for the end I peppered them throughout the page so as to have some level of context and cohesion with the twelve months that preceded them. It’s tricky, with these things, to fall into the disease of more: I want to write more, I want to lift more, I want to build something new, I want to watch more films, et cetera. That’s the easy part!

The truth is, I have operated the last nine months or so with absolutely no slack. The vast majority of days this year were bereft of even thirty minutes to relax and gather my thoughts. This is a bit of a bummer: the superstructure I built out around my life might have been feasible in a world where I was locked down and could have complete mastery of every single hour being spent or whatever, but that’s a) inherently unsustainable; b) especially unsustainable in a year where I changed my job and am once again subject to the whims of a social life.

Really, the question that is worth posing is: what do I want to do less of? Where is the time — and energy — going to come from? (And even that dichotomy is interesting to me. One of the most interesting parts of being in management now is internalizing that your time is no longer your own: something like 60% of my time is given away to others, either in the form of meetings or in the form of being in “reaction mode”.)

(An aside — It’s hard for me to stop doing things in general. One of the downsides of habits is that we think of consistency as a virtue, even if its consistency in something that’s value-neutral. I legitimately thought long and hard about ending my 700-day Duolingo streak because even though I stopped giving a shit about French, it felt bad to break the chain!)

I think the answer, then, is going to be a bit to-be-determined. But a quick perusal of iOS’ “Screen Time” report reveals that there’s a lot of low-hanging fruit.

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