Getting into the room and hating it

When I walked out of my 9-5 for the last time, I didn't give much thought to what had gone wrong. I'd left three jobs in five years, two of them dream jobs on paper. The other was a stretch, but that's okay.

I'd been diagnosed with autism the year before. I'd overextended myself and failed to find the narrow conditions which allow me to thrive. The pandemic and its normalization of remote-first environments played a role too. I thought this was an open and shut case.

But as I creep up on one year of self-employment, I realize there was another component missing in my transportation career.

I didn’t have my own work.

I’d built a professional house of cards that went roughly like this:

Me: I want to improve public transit.

Them: Awesome! How do you plan to do that?

Me: Whatever you hire me to do!

Sure, I had some ideas on how to improve transit globally. But I didn’t feel there was much I could do as a lowly software engineer or engineering manager.

I kept telling myself I’d meet a professional bestie and we’d build cool things together. They’d be the mouthpiece, and I’d quietly build and ideate in the background. That felt more comfortable, but also left me waiting.

Turns out, ambition and second-in-command energy is a recipe for disillusionment.

Without my own work, I had nothing to fall back on when the environment became challenging and remained invalidating.

Two instances stand out as times I tried to create my own work. Why they failed would ultimately inform what I’m trying to do differently this time around.

In the first example, I stumbled into a research project designed to help me become an expert on transit in NYC. Why someone didn’t just hand me my autism certificate then and there still confuses me. Naturally, I collected every New York Times article from each fare increase since the 1904 nickel fare. I built an open-source tool to compile my notes and make them public. (This still exists, but I didn’t add the 2023 rise because I burned out too hard on this project. Please don’t show up to the station 15-cents shy.) I tried to wrap it all up in a digestible blog post. Something that would signal to myself (and maybe the public) that this cadence of deep research and shareable insights was here to stay.

The only problem? I built it all and felt physically unable to share. I can write a satirical op-ed about a fake coffee van without blinking, but writing one sentence of actual nonfiction and expecting it to stand the test of time (and 2017 Twitter) was beyond me. It took a caffeine trance and a brief surge of confidence to get the blog post out the door.

A few days later a New York Post reporter messaged me and asked me to call them. My plan had worked! I’d gotten attention for the thing I made.

Our five-minute phone call was my first glimpse of being in a room I’d craved, only to realize my nervous system wanted out. They were looking for a hot take. I was hoping to connect with someone over what I’d learned.

I couldn’t even muster a lukewarm take. I froze.

It wouldn’t be the last time someone assumed my microphone was broken, when in fact I was just speechless. Stuck trying to decode how they could be asking for something so different than what I was offering.

Getting into the room is one skill, not hating it is a totally different animal.

The second example took place within a company which was what the young kids would call mid. Mid-sized, mid-hip, and mid-social, it checked a lot of boxes! I found myself in a period of organizational stability with a manager who encouraged me to play to my strengths. I spent six months building a highly technical system and it was a success. I felt satisfied to know the system I built helped transit riders have smoother journeys in multiple cities.

Not long after, that manager was fired (for unrelated reasons), and his replacement told me my project had been unnecessary. Unsure whether I was supposed to fight for it or fall in line, I froze. This time, for longer than a phone call. The amount of effort I gave the new manager before I resigned the next year was on the order of hours.

That job showed me how fragile my goals were when tied to a company’s. I’m wired for the work, not the political theatre around it. I honestly believe I could write code in binary—or support an engineer who commits to doing the same—but my brain will not form a sentence about which project should win in a turf war.

And yet, because I presented as social and ambitious, people kept expecting me to do more of the latter. And I believed them! The gap between what I seemed suited for and what I could actually sustain wore me down.

One last hurdle I had to clear was letting go of the need to impress people. Most of my side projects were attempts to get the next job, where I would once again be at the whims of whatever management wanted me to build. (Countering this by becoming management myself would fail in a different way, but that’s a different piece.)

The place I find myself now is still early, but different. I’m building a small business and this time it’s backed by real work.

I publish a piece of writing most Mondays that I enjoy penning. I’ve put two years of work into a Python interpreter, which exists (and works) just because I wanted it to.

And while this piece is mostly about my solo work, the 1:1 side of my business matters just as much. A call with a client who’s excited to learn or build is so much more satisfying than a manager asking for three bullet points for their weekly update.

When marketing myself gets overwhelming (which is OFTEN), I take the next day slower. Take a walk in my city, write some code, write some prose.

That’s what makes it sustainable.