The Paradox of Comfortable Enough

Last week, my team was alerted about an error showing up across all of our testing environments. We were concerned. This could be a new bug about to reach production. I dug into the logs, traced the problem to a new feature behind a toggle, and we turned the toggle off before deploying. Crisis handled. Everyone was at peace.

Later that day, a colleague picked up the bug ticket I'd created. He ran into trouble testing the fix, so we looked at the code together. It was a tricky problem, something subtle in how the feature interacted with existing logic. After debugging it, I was able to show him exactly what was causing the issue. That unblocked him, and I went back to my own work.

A few hours later I closed my laptop feeling good. Accomplished. Later, on one of my usual walks after dinner, the thought came back again: How many more years before I own my time?

I reached a place in my career where I get to enjoy many benefits beyond a paycheck. This took decades of career pivots to reach: manufacturing, LAN engineering, programming. Walking away feels like walking away from half of my life's work. At my age and with 11 years at one company, there are many compounding benefits: salary growth, institutional knowledge, the kind of trust that takes years to build. All of this adds up to a life of comfort that I worked hard to obtain. This is what people call the golden handcuffs, and I've come to realize that mine aren't made of pain and suffering. They're made of comfort. That's why they work.

For the first two decades of my professional life, leaving a job was a binary decision. If I didn't like my job, I'd find a new one. I knew time was currency, and at the time I had plenty. I ran into many barriers along the way. Not knowing the language, not having experience or diplomas. But the truth is that if I spent enough time searching and applying, eventually I'd find a job.

Today there is a third option I need to consider. It's no longer between liking my job or not liking it. The third answer is: "Yes, I like my job. And I need something else." Not because what I have is broken, but because something in me is asking for more control over my time, my output, my direction. And with fewer years of professional work ahead of me than behind me, the bet on something that is "fine" starts to feel like something I'm running out of time to settle for.

This isn't a midlife crisis. A midlife crisis is buying a sports car or a facelift. This is a midlife calculation.

For more than a few decades, I've spent my career optimizing systems: databases, architectures, processes. It's no surprise to me that this mental model is now seeping into how I think about my life. I want the highest return on my investment. I want to minimize the time I spend doing something that's just fine.

But optimization assumes that you've defined the right objective function, and that's something I think I'm close to defining. The responsible career professional in me says: stay put. If my goal is to maximize lifetime earnings, staying is the obvious choice. If my goal is to maximize time under my control before I run out of years, the math changes entirely. At my age, the denominator is shrinking whether I optimize or not.

In What I Talk About When I Talk About Running, Murakami describes his path to becoming a novelist. He sold his profitable jazz bar to write. His friends told him he was irrational, but his answer was about commitment, not calculation. I've learned that some decisions aren't optimization problems. They're identity questions, the kind that don't resolve in spreadsheets. The tools that have served me well in my career are the same ones that can mislead me about my life at this stage. I need to define what I want, and be aware that the optimal choice might not be the right one.

I'm not quitting. I'm not making a dramatic move. I'm doing something harder: building in parallel. Keeping the job that funds my life while carving out the hours to build something that might eventually fund a different one. The paradox of "comfortable enough" is that it gives you the runway to build, but also every reason not to.

Most weeks, the building happens in the margins. Early mornings, evenings, weekends. That's not inspirational. It's just true. And it's the reality for anyone else in this position.

Finishing my walk around Bellevue's downtown park, I watched the ducks flapping on the water, dogs walking with their humans, a sunset fading above the buildings. It was a good day. And the question was still there as I turned toward home. I think it's supposed to be. Maybe the question is the engine — the thing that keeps me building, keeps me writing, keeps me showing up here every Friday.

How many more years before I own my time?