Why do I work?

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 as it may seem, I came to revere beating myself up without even realizing it. In fact, I realized I’d been doing it most of my life. Notably I didn’t do it as a young kid. But over time a confluence of circumstances caused me to believe I was a piece of shit that required constant vigilance in order to be kept on the straight and narrow.

One of the biggest things I remember from sliding my toes in to the spotlight was a comment made that really rubbed me the wrong way:

These symptoms are a classic sign of burn out. One thing I notice in your writing is you’re very tied up in things having meaning and mattering in some specific way.

- fnordpiglet³

I’m slowly coming to realize that when something rubs me the wrong way, there’s a nugget of gold hiding in it. At first I was totally put off by the “abandonment of meaning” the commenter was suggesting. My mind went something like this: “what a serf. He doesn’t realize that a life without meaning is no life at all. I’ll show him. I’ll show all of them when I make something of myself and find the meaning I’ve always longed for.”

And then he recommended that I adopt a daily meditation practice. I was like, “fuck off, bro.” And you know what? I eventually did adopt a daily meditation practice. And you know what? It was exactly what I needed. Turns out humble pie can be pretty tasty!

Before I recognized the veracity of fnordpiglet’s words, I had a few more steps to make. I was so burned out at Stripe that I quit weeks away from vesting a large chunk of stock worth a lot of money. I was so beside myself that money stopped mattering.

And an incredible thing happened while I sat on my back porch watching the birds play in the sunlight. I started dreaming again. I had forgotten what it felt like to dream. To allow my mind to wander into the realms of possibility without limitation or expectation and just… dream.

As you may have guessed, it didn’t last long. I had a short and intense burst of creativity and drive that quickly came crashing into the reality of needing to make money. I have two kids and a wife and we live off my income. I ended up getting another remote job and found myself settling back into my old patterns. I was at that job for a year before a Thatch recruiter reached out to me.

At that point I’d given up on finding my “dream job.” I’d spent hours scouring job posting boards and I was growing tired of all the “AI will change the world and you can too!” bullshit that seemed to fill every crack of the job market. I was coming to see that a dream job didn’t actually exist. Everything was shit in its own unique way. But Thatch reached deep into my psyche and tickled that “meaning” part of my brain. They presented me with a mission that felt meaningful. They seemed like genuinely caring people trying to make a dent in the awfulness that is the American healthcare system.

Personally, I’d experienced the shittiness of being tied to a single healthcare provider that was dictated by my employer. The idea that I could receive a stipend from my employer to purchase my own insurance, and use the left funds to make health related purchases, was extremely enticing.

And so I found myself once again hopping on the mission train. I was going to fix healthcare and save the world. I’d have to learn Ruby to do it, but sacrifices must be made.

I still work at Thatch. I actually think it’s a great company. It isn’t as much the company that’s changed, it’s me⁴. Sure, we’ve got warts, just like everything else, but I’m coming to realize that everything does. Life, and work, is more a matter of accepting what is instead of trying so hard to make it something it isn’t. And in letting go⁵ I find the meaning I’ve always been looking for. A paradox for sure.

And further still I’ve come to realize that the way I treat myself is intractably linked to the way I approach work. I hate being controlled. Any time I feel an impending sense of control, I freeze up internally. But being controlled is a function of my perception. Even if someone is breathing down my neck, so to speak, it’s possible to let go of the pressure I feel inside. It’s truly liberating.

So, back to the question “why do I work?” Because work is life. The boundaries between these concepts are indeed illusions. So the real question is: “why do I live?” And that, my friends, is a wonderful question. And often questions are better than concrete answers.

The next time we feel a sense of dread, let’s remember to take a deep breath. It might be the last one we get! I hope you have a lovely day ❤️.