Thoughts on Motivation and My 40-Year Career

The struggle is what brings your ideals to life. 💜

I’ve never published an essay quite like this. I’ve written about my life before, reams of stuff actually, because that’s how I process what I think, but never for public consumption.

I’ve been pushing myself to write more lately because my co-authors and I have a whole fucking book to write between now and October. After ten years, you’d think this would be getting easier, not harder.

There’s something about putting out such memoiristic material that feels uncomfortably feminine to me. (Wow, ok.) I want to be known for my work, not for having a dramatic personal life. I love my family and don’t want to put them on display for the world to judge. And I never want the people I care about to feel like I am mining their experiences for clicks and content, whether that’s my family or my coworkers.

Many of the writing exercises I’ve been doing lately have ended up pulling on threads from my backstory, and the reason I haven’t published them is because I find myself thinking, “this won’t make any sense to people unless they know where I’m coming from.”

So hey, fuck it, let’s do this.

I went to college at the luckiest time

I left home when I was 15 years old. I left like a bottle rocket taking off – messy, explosive, a trail of destruction in my wake, and with absolutely zero targeting mechanisms.

It tells you a lot about how sheltered I was that the only place I could think of to go was university. I had never watched TV or been to a sports game or listened to popular music. I had never been to a doctor, I was quite unvaccinated.

I grew up in the backwoods of Idaho, the oldest of six, all of us homeschooled. I would go for weeks without seeing anyone other than my family. The only way to pass the time was by reading books or playing piano, so I did quite a lot of both. I called up the University of Idaho, asked for an admissions packet, hand wrote myself a transcript and gave myself all As, drove up and auditioned for the music department, and was offered a partial ride scholarship for classical piano performance.

I told my parents I was leaving, with or without their blessing or financial support. I left with neither.

My timing turned out to be flawless. I arrived on the cusp of the Internet age – they were wiring dorms for ethernet the year I enrolled. Maybe even more important, I arrived in the final, fading glory years of affordable state universities.

I worked multiple minimum wage jobs to put myself through school; day care, front desk, laundry, night audit. It was grueling, round the clock labor, but it was possible, if you were stubborn enough. I didn’t have a Social Security number (long story), I wasn’t old enough to take out loans, I couldn’t get financial aid because my parents didn’t file income taxes (again, long story). There was no help coming, I sank or I swam.

I found computers and the Internet around the same time as it dawned on me that everybody who studied music seemed to end up poor as an adult. I grew up too poor to buy canned vegetables or new underwear; we were like an 1800s family, growing our food, making our clothes, hand-me-downs til they fell apart.

Fuck being poor. Fuck it so hard. I was out.

I lost my music scholarship, but I started building websites and running systems for the university, then for local businesses. I dropped out and took a job in San Francisco. I went back, abortively; I dropped out again.

By the time I was 20 I was back in SF for good, making a salary five times what my father had made.

I grew up with a very coherent belief system that did not work for me

A lot of young people who flee their fundamentalist upbringing do so because they were abused and/or lost their faith, usually due to the hypocrisy of their leaders. Not me. I left home still believing the whole package – that evolution was a fraud, that the earth was created in seven days, that woman was created from Adam’s rib to be a submissive helpmate for their husband, that birth control was a sin, that anyone who believed differently was going to hell.

My parents loved us deeply and unshakably, and they were not hypocrites. In the places I grew up, the people who believed in God and went to church and lived a certain way were the ones who had their shit together, and the people who believed differently had broken lives. Reality seemed to confirm the truth of all we were taught, no matter how outlandish it sounds.

So I fully believed it was all true. I also knew it did not work for me. I did not want a small life. I did not want to be the support system behind some godly dude. I wanted power, money, status, fame, autonomy, success. I wanted to leave a crater in the world.

I was not a rebellious child, believe it or not. I loved my parents and wanted to make them proud. But as I entered my teens, I became severely depressed, and turned inward and hurt myself in all the ways young people do.

I left because staying there was killing me, and ultimately, I think my parents let me go because they saw it too.

Running away from things worked until it didn’t

I didn’t know what I wanted out of life other than all of it; right now, and my first decade out on my own was a hoot. It was in my mid twenties that everything started to fall apart.

I was an earnest kid who liked to study and think about the meaning of life, but when I bolted, I slammed the door to my conscience shut. I knew I was going to hell, but since I couldn’t live the other way, I made the very practical determination based on actuarial tables that I could to go my own way for a few decades, then repent and clean up my shit before I died. (Judgment Day was one variable that gave me heartburn, since it could come at any time.)

I was not living in accordance with my personal values and ethics, to put it lightly. I compartmentalized; it didn’t bother me, until it did. It started leaking into my dreams every night, and then it took over my waking life. I was hanging on by a thread; something had to give.

My way out, unexpectedly, started with politics. I started mainlining books about politics and economics during the Iraq War, which then expanded to history, biology, philosophy, other religious traditions, and everything else. (You can still find a remnant of my reading list here.)

When I was 13, I had an ecstatic religious experience; I was sitting in church, stewing over going to hell, and was suddenly filled with a glowing sense of warmth and acceptance. It lasted for nearly two weeks, and that’s how I knew I was “saved”.

In my late 20s, after a few years of intense study and research, I had a similar ecstatic experience walking up the stairs from the laundry room. I paused, I thought “maybe there is no God; maybe there is nobody out there judging me; maybe it all makes sense”, and it all clicked into place, and I felt high for days, suffused with peace and joy.

My career didn’t really take off until after that. I always had a job, but I wasn’t thinking about tech after hours. At first I was desperately avoiding my problems and self-medicating, later I became obsessed with finding answers. What did I believe about taxation, public policy, voting systems, the gender binary, health care, the whole messy arc of American history? I was an angry, angry atheist for a while. I filled notebook after notebook with handwritten notes; if I wasn’t working, I was studying.

And then, gradually, I wound down. The intensity, the high, tapered off. I started dating, realized I was poly and queer, and slowly chilled the fuck out. And that’s when I started being able to dedicate the creative, curious parts of my brain to my job in tech.

Why am I telling you all this?

Will Larson has talked a lot about how his underlying motivation is “advancing the industry”. I love that for him. He is such a structured thinker and prolific writer, and the industry needs his help, very badly.

For a while I thought that was my motivation too. And for sure, that’s a big part of it, particularly when it comes to observability and my day job. (Y’all, it does not need to be this hard. Modern observability is the cornerstone and prerequisite for high performing engineering teams, etc etc.)

But when I think about what really gets me activated on a molecular level, it’s a little bit different. It’s about living a meaningful life, and acting with integrity, and building things of enduring value instead of tearing them down.

When I say it that way, it sounds like sitting around on the mountain meditating on the meaning of life, and that is not remotely what I mean. Let me try again.

For me, work has been a source of liberation

It’s very uncool these days to love your job or talk about hard work. But work has always been a source of liberation for me. My work has brought me so much growth and development and community and friendship. It brings meaning to my life, and the joy of creation. I want this for myself. I want this for anyone else who wants it too.

I understand why this particular tide has turned. So many people have had jobs where their employers demanded total commitment, but felt no responsibility to treat them well or fairly in return. So many people have never experienced work as anything but a depersonalizing grind, or an exercise in exploitation, and that is heartbreaking.

I don’t think there’s anything morally superior about people who want their work to be a vehicle for personal growth instead of just a paycheck. I don’t think there’s anything wrong with just wanting a paycheck, or wanting to work the bare minimum to get by. But it’s not what I want for myself, and I don’t think I’m alone in this.

I feel intense satisfaction and a sense of achievement when I look back on my career. On a practical level, I’ve been able to put family members through college, help with down payments, and support artists in my community. All of this would have been virtually unimaginable to me growing up.

I worked a lot harder on the farm than I ever have in front of a keyboard, and got a hell of a lot less for my efforts.

(People who glamorize things like farming, gardening, canning and freezing, taking care of animals, cooking and caretaking, and other forms of manual labor really get under my skin. All of these things make for lovely hobbies, but subsistence labor is neither fun nor meaningful. Trust me on this one.)

My engineer/manager pendulum days

I loved working as an engineer. I loved how fast the industry changes, and how hard you have to scramble to keep up. I loved the steady supply of problems to fix, systems to design, and endless novel catastrophes to debug. The whole Silicon Valley startup ecosystem felt like it could not have been more perfectly engineered to supply steady drips of dopamine to my brain.

I liked working as an engineering manager. Eh, that might be an overstatement. But I have strong opinions and I like being in charge, and I really wanted more access to information and influence over decisions, so I pushed my way into the role more than once.

If Honeycomb hadn’t happened, I am sure I would have bounced back and forth between engineer and manager for the rest of my career. I never dreamed about climbing the ladder or starting a company. My attitude towards middle management could best be described as amiable contempt, and my interest in the business side of things was nonexistent.

I have always despised people who think they’re too good to work for other people, and that describes far too many of the founders I’ve met.

Operating a company draws on a different kind of meaning

I got the chance to start a company in 2016, so I took it, almost on a whim. Since then I have done so many things I never expected to do. I’ve been a founder, CEO, CTO, I’ve raised money, hired and fired other execs, run organizations, crafted strategy, and come to better understand and respect the critical role played by sales, marketing, HR, and other departments. No one is more astonished than I am to find me still here, still doing this.

But there is joy to be found in solving systems problems, even the ones that are less purely technical. There is joy to be found in building a company, or competing in a marketplace.

To be honest, this is not a joy that came to me swiftly or easily. I’ve been doing this for the past 9.5 years, and I’ve been happy doing it for maybe the past 2-3 years. But it has always felt like work worth doing. And ultimately, I think I’m less interested in my own happiness (whatever that means) than I am interested in doing work that feels worth doing.

Work is one of the last remaining places where we are motivated to learn from people we don’t agree with and find common pursuit with people we are ideologically opposed to. I think that’s meaningful. I think it’s worth doing.

Reality doesn’t give a shit about ideology

I am a natural born extremist. But when you’re trying to operate a business and win in the marketplace, ideological certainty crashes hard into the rocks of reality. I actually find this deeply motivating.

I spent years hammering out my own personal ontological beliefs about what is right and just, what makes a life worth living, what responsibilities we have to each another. I didn’t really draw on those beliefs very often as an engineer/manager, at least not consciously.

That all changed dramatically after starting a company.

It’s one thing to stand off to the side and critique the way a company is structured and the decisions leaders make about compensation, structure, hiring/firing, etc. But creation is harder than critique (one of my favorite Jeff Gray quotes) — so, so, so much harder. And reality resists easy answers.

Being an adult, to me, has meant making peace with a multiplicity of narratives. The world I was born into had a coherent story and a set of ideals that worked really well for a lot of people, but it was killing me. Not every system works for every person, and that’s okay. That’s life. Startups aren’t for everyone, either.

The struggle is what brings your ideals to life

Almost every decision you make running a company has some ethical dimension. Yet the foremost responsibility you have to your stakeholders, from investors to employees, is to make the business succeed, to win in the marketplace. Over-rotating on ethical repercussions of every move can easily cause you to get swamped in the details and fail at your prime directive.

Sometimes you may have a strongly held belief that some mainstream business practice is awful, so you take a different path, and then you learn the hard way why it is that people don’t take that path. (This has happened to me more times than I can count. 🙈)

Ideals in a vacuum are just not that interesting. If I wrote an essay droning on and on about “leading with integrity”, no one would read it, and nor should they. That’s boring. What’s interesting is trying to win and do hard things, while honoring your ideals.

Shooting for the stars and falling short, innovating, building on the frontier of what’s possible, trying but failing, doing exciting things that exceed your hopes and dreams with a team just as ambitious and driven as you are, while also holding your ideals to heart — that’s fucking exciting. That’s what brings your ideals to life.

We have lived through the golden age of tech

I recognize that I have been profoundly lucky to be employed through the golden age of tech. It’s getting tougher out there to enter the industry, change jobs, or lead with integrity.

It’s a tough time to be alive, in general. There are macro scale political issues that I have no idea how to solve or fix. Wages used to rise in line with productivity, and now they don’t, and haven’t since the mid 70s. Capital is slurping up all the revenue and workers get an ever decreasing share, and I don’t know how to fix that, either.

But I don’t buy the argument that just because something has been touched by capitalism or finance it is therefore irreversibly tainted, or that there is no point in making capitalist institutions better. The founding arguments of capitalism were profoundly moral ones, grounded in a keen understanding of human nature. (Adam Smith’s “Wealth of Nations” gets all the attention, but his other book, “Theory of Moral Sentiments”, is even better, and you can’t read one without the other.)

As a species we are both individualistic and communal, selfish and cooperative, and the miracle of capitalism is how effectively it channels the self-interested side of our nature into the common good.

Late stage capitalism, however, along with regulatory capture, enshittification, and the rest of it, has made the modern world brutally unkind to most people. Tech was, for a shining moment in time, a path out of poverty for smart kids who were willing to work their asses off. It’s been the only reliable growth industry of my lifetime.

It remains, for my money, the best job in the world. Or it can be. It’s collaborative, creative, and fun; we get paid scads of money to sit in front of a computer and solve puzzles all day. So many people seem to be giving up on the idea that work can ever be a place of meaning and collaboration and joy. I think that sucks. It’s too soon to give up! If we prematurely abandon tech to its most exploitative elements, we guarantee its fate.

If you want to change the world, go into business

Once upon a time, if you had strongly held ideals and wanted to change the world, you went into government or nonprofit work.

For better or for worse (okay, mostly worse), we live in an age where corporate power dominates. If you want to change the world, go into business.

The world needs, desperately, people with ethics and ideals who can win at business. We can’t let all the people who care about people go into academia or medicine or low wage service jobs. We can’t leave the ranks of middle and upper management to be filled by sycophants and sociopaths.

There’s nothing sinister about wanting power; what matters is what you do with it. Power, like capitalism, is a tool, and can be bent to powerful ends both good and evil. If you care about people, you should be unashamed about wanting to amass power and climb the

ladder.

There are a lot of so-called best practices in this industry that are utterly ineffective (cough, whiteboarding B-trees in an interview setting), yet they got cargo culted and copied around for years. Why? Because the company that originated the practice made a lot of money. This is stupid, but it also presents an opportunity. All you need to do is be a better company, then make a lot of money. 😉

People need institutions

I am a fundamentalist at heart, just like my father. I was born to be a bomb thrower and a contrarian, a thorn in the side of the smug moderate establishment. Unfortunately, I was born in an era where literally everyone is a fucking fundamentalist and the establishment is holding on by a thread.

I’ve come to believe that the most quietly radical, rebellious thing I can possibly do is to be an institutionalist, someone who builds instead of performatively tearing it all down.

People need institutions. We crave the feeling of belonging to something much larger than ourselves. It’s one of the most universal experiences of our species.

One of the reasons modern life feels so fragmented and hard is because so many of our institutions have broken down or betrayed the people they were supposed to serve. So many of the associations that used to frame our lives and identities — church, government, military, etc — have tolerated or covered up so much predatory behavior and corruption, it no longer surprises anyone.

We’ve spent the past few decades ripping down institutions and drifting away from them. But we haven’t stopped wanting them, or needing them.

I hope, perhaps naively, that we are entering into a new era of rebuilding, sadder but wiser. An era of building institutions with accountability and integrity, institutions with enduring value, that we can belong to and take pride in… not because we were coerced or deceived, not because they were the only option, but because they bring us joy and meaning. Because we freely choose them, because they are good for us.

The second half of your career is about purpose

It seems very normal to enter the second half of your 40 year career thinking a lot about meaning and purpose. You spend the first decade or so hoovering up skill sets, the second finding your place and what feeds you, and then, inevitably, you start to think about what it all means and what your legacy will be.

That’s definitely where I’m at, as I think about the second half of my career. I want to take risks. I want to play big and win bigger. I want to show that hard work isn’t just a scam inflicted on those who don’t know any better. If we win, I want the people I work with to earn lifechanging amounts of money, so they can buy homes and send their kids to college. I want to show that work can still be an avenue for liberation and community and personal growth, for those of us who still want that.

I care about this industry and the people in it so much, because it’s been such a gift to me. I want to do what I can to make it a better place for generations to come. I want to build institutions worth belonging to.

Charity and Bubba, communing.