Why do I work?

Why do I work?<br>2026-08-21<br>This was written with old fashioned human intelligence. No AI was harmed in the making of this blog post either for writing or editing.

At first glance the title of this post may seem odd, obvious, or maybe just pointless. Regardless, it’s an important question to me. And it’s been harder to detangle than I expected. The journey of answering that single question has been both a profound source of personal insight and a wellspring of ostensible nightmares. I’ve been wrestling with it for years. Let’s take a journey through my mind and see if we can have some fun together along the way.

I first encountered computers as a workaround for parental rules against video games. My parents wouldn’t let me buy an N64, so I was left with what I perceived as second best: a desktop PC. As long as whatever I did with the computer had some vague connection to education I could get away with it. I spent much of my childhood on computers. There was something consistently alluring about them. The idea that words could be written (in a mystical language called C) that created entire worlds within a screen was endlessly fascinating and perplexing to me. The game Myst stands out as a poignant example and metaphor from that era.

When the time came to go to college, I chose computer science. I struggled through the requisite math classes and finally got to write some honest-to-god Java. I sucked at it. I vividly recall sweating through my shirt as I frantically scribbled down half-baked programs on my final exam with a pencil on paper as the test timer expired. I thought, “if this is anything like what programming is like, I want nothing to do it. I’m a people person. I’m not cut out for this cubicle crap.” I dropped out of CS after completing the first year and considered moving away and studying art.

Practicality got hold of me and I decided to follow in my dad’s footsteps1 and pursue a degree in business. I settled for some geekiness and got my degree in information systems where there were no hand-written coding tests. I triple checked that before signing on to the program.

I graduated and got a job as a glorified Excel consultant. I’d drive all over the greater Portland area wrangling the gnarliest of Excel spreadsheets. Okay, let’s be real, I was helping people make the gnarliest of spreadsheets. One of my projects involved embedding a several gigabyte columnar database within a spreadsheet to help a political advocacy group determine which voters to target. Truly the stuff of nightmares.

After a while I realized I was hitting the limits of what I could express with the various tools in the Microsoft ecosystem. And so I decided to get back into coding. I’d stay up late teaching myself to code while my wife slept next to me in bed. I recall the first time I successfully sent JSON from a server and parsed it in the browser to show the items of a todo list. In that moment, the world suddenly got brighter. I started to believe that nothing was beyond my abilities if I just learned to code well enough. Software was the reality shaping language I’d been looking for.

That belief propelled me to transition my career quickly into programming. I jumped jobs a few times, worked for a failing startup, and did a long stint in ad tech. I loved it. I used to wake up at 4:30am just to get in to the office before the sunrise because I loved working in the quiet dark before the bustle of the day began. Eventually the company I worked for got bought by AT&T. At first I was excited to be a part of such a household name. But reality hit fast as I watched my co-worker friends all jump ship and go to cooler places like Stripe.

Ahh, Stripe. Odd as it may seem, I came to revere the company. I’d devour podcasts that Patrick was on, I’d check hackernews every day for new product announcements, I’d peruse their site and admire the skill and craftsmanship with which they did everything. In my imagination Stripe became larger than life. It became a symbol of the power of words in a computer. With only seven lines of code, two young brothers could conquer the financial world and wrestle it into something beautiful for developers like me.

I worked at Stripe for nearly 4 years. It was a rollercoaster2. It was where I realized that mental health was a real thing that demanded my attention. It was where the question of “why do I work” began to take root. A simpler way of putting all that: my life, as I knew it, got totally fucked. For some reason I decided to write about it publicly. And for some other reason my article hit the front page of hackernews.

I’d never felt so excited and exposed in my life. There was a thrill in having people see me publicly. And there was a dread too. I “gently” forced myself to read every comment and see if there were any lessons I could glean from the snippets of passersby. In some ways I turned the whole thing into another reason to beat myself up.

Ahh beating myself up. Odd...