Applied Cartography, or: How I Have Been

June 8th, 2023

I know some of you were top of your class in high school. Maybe you're used to getting 100% on math tests. Well, this is engineering, not math. If you graduate at the top of your engineering class, we should fail you. It means you didn't learn engineering. You wasted your time. Unless you're going to grad school, nobody in the world cares if you got an 80% or a 99%. Do as little work as you can, to learn most of what we're teaching and graduate with a passable grade and get your money's worth. That's engineering. —apenwarr

Dearest friend, noblest reader:

I've been writing online for over a decade now — under a variety of names, on a variety of platforms. Some of them are still online, preserved in amber (or, I suppose, a bright-neon-blue that felt very correct to my circa-2019 aesthetic sensibilities).

I've changed over the past decade; the reasons I write have, too.

When I was a greasy-faced new grad from a liberal arts college with no computer science pedigree to speak of, I wrote programming tutorials to try and establish myself as a "real programmer", back when I thought a "real programmer" was a distinct identity, someone Californian with a GitHub hoodie and a sticker-laden MacBook. Success looked like briefly appearing at the top of Hacker News; I remember with no small amount of fondness when I woke up to find that a quick hit post was above the fold and I suddenly had more readers than I'd ever had before. (The comments are still around, btw.)

Once I finally entered "the industry", as they say, with a resumé that (I mean this with realpolitik, not braggadocio — there are few things less odious about the industry than the fact that admittance to one company confers upon you admittance to every other company) obviates the need for social proof, the goal of my writing turned to other pursuits. I launched a product; almost all of my writing energy went to (implicit and/or explicit) content marketing for that product, and what little remained was spent writing at Stripe to a smaller audience.

With great and solemn portent, my teacher announced she would tell us something that her teacher had told her, and that her teacher’s teacher had told him, and so on, back to Yeats: The thing to remember is that no one ever finds out that you don’t know what you’re doing. —Sarah Manguso

I've worked independently for the past year, and I am quite proud of Buttondown — it's doubled in revenue and, more importantly, roughly quintupled in product quality.

Much of this is due to writing: writing feature announcements, writing changelog entries, writing documentation, writing job postings, writing emails, writing tweets, writing for work's sake. I have gone from writing code for twenty hours a week to writing code for twenty hours a week and writing prose for twenty hours a week. (This is also true of maturing from a junior developer into a senior one at most companies: your IDE slowly shifts from VS Code to Google Docs.)

This is all, to be clear, rapturously delightful.

I currently am in my favorite job of all time, the one I dreamed of having ten years ago when I was cranking out banal blog posts about five things you might not have known about the Python stdlib. But I find myself missing what Anne Lamott refers to as the tea ceremony of it all:

Writing has so much to give, so much to teach, so many surprises. That thing you had to force yourself to do—the actual act of writing—turns out to be the best part. It’s like discovering that while you thought you needed the tea ceremony for the caffeine, what you really needed was the tea ceremony. The act of writing turns out to be its own reward. —Anne Lamott

What I am trying to say is: writing for work is a skill, and its one I'm grateful that I get to practice with some level of regularity and success, but consensus-building and changelog-writing and technical documentation does not scratch quite the same itch as just bopping around on iA Writer, trying to find a through-line in a series of disparate thoughts.

Over the next few weeks, I'll be writing four essays:

  • Spoonbill (2016 — 2023), the mostly-accidental rise and fall of a $4500 MRR side project from which I collected checks for three years without writing a single line of code.
  • PTO is Fake, about how to pragmatically think about navigating corporate culture.
  • How to Spot Trapdoors, a series of three heuristics for identifying risky technical decisions.
  • Sic the Goon Squad on 'Em, a retrospective of all of my biggest worries about Buttondown-circa-2018 and how insanely foolish they were.

I will probably write more — I encourage you to tell me what you'd be interested in hearing about — but that list enough gives me an excitement at the prospect of writing that has been too-long absent from my weeks.

I have nothing to sell you; I just miss thinking hard about things in the way that good writing requires. I cannot guarantee that it'll be your while; you'll have to settle for a promise of good faith.

Applied Cartography is an aperiodic series of essays about product, process, and technology written by Justin Duke.