From Cynic to Stoic

Cleanup on Aisle 2003

Last week was a rough one. A catastrophic failure in our basement plumbing, and my birthday spent cleaning and salvaging anything that could be saved.

Still in that clean-out mood, I figured I’d do some housekeeping on the blog too: fix a few dead links, prune some tags. But scrolling back through twenty-plus years of posts, I stopped on a question I’d never actually asked myself: how do the changes in my writing reflect the changes in me?

So I asked my Claude coach to roll up its sleeves and go to work. Read everything, analyze the content and infer changes in my tone, voice, identity, values, and world-view. And to be brutally honest.

The Eras Tour (Sonnek’s Version)

What came back was a surprise to say the least. Twenty years of writing distilled into three distinct eras with meaningful differences in the written tone, individual identity, and underlying beliefs.

The Ranter The Ranter · 2003–2007
The combative developer frustrated at his day-job and allergic to anyone who didn't "get it."
The Builder The Builder · 2008–2014
Left large-corporate for a startup environment, shipped open-source libraries and shifted ownership from "my code" to "our code" leading teams.
The Leader The Leader · 2015–2026
Leading product/engineering teams where individual impact is funneled directly through the surrounding teams.

These eras track my career cleanly enough, from coder to leader. But the roles were just the surface. Underneath was a shift in disposition, which the analysis put plainly:

The old self was a curious, defended perfectionist: hungry for ideas, distrustful of people, ego fused to being right. The current self is a curious, open builder: the same appetite for ideas, but ability is now malleable, being wrong is information, and talent is assumed to be everywhere.

The Candid Mirror

I sat with this analysis for quite some time. Claude did not pull any punches. Who was that “Ranter” version of me? I barely recognized him, and he was not kind. I viewed the world as black and white…me versus everyone else. The “other people” who didn’t “get it”, and the “mindless drones.” I told frustrated developers they should “consider tossing yourself from a balcony.” I called software that I didn’t like “one of the greatest crimes against humanity I have witnessed in recent history.” When someone struggled with software I’d built, I blamed the user instead of identifying the bugs in my own platform.

What was the source of The Ranter’s cynicism? One explanation really resonated with me:

Scratch the surface of most cynics and you find a frustrated idealist, someone who made the mistake of converting his ideals into expectations. - Peter Senge (The Fifth Discipline)

That’s exactly it. I was an idealist who turned strong opinions into unspoken expectations of everyone else, then got worked up when they behaved differently. Ego and pride in the driver’s seat, certain my opinions were the right ones.

The Shift

So what changed? There was no lightbulb moment, and no single cause I can point to. It was slow and arduous, a handful of forces pulling in the same direction over many years, because the beliefs that drive behavior take a long time to rewire.

The obvious ones came from external events. I got married, and had kids along the way. My career walked me from writing code alone, to leading teams, to leading leaders. Each step widened the aperture and I matured as an person. It’s hard to keep sorting the world into people who “get it” when my whole job becomes helping other people get there, and hard to stay at war with a world where I’m busy raising a family.

The deeper change came from years of deliberate innerwork. I’ve learned to identify what I can and can’t control through the foundational practice and philosophy of Stoicism and my faith. And I’ve been incredibly fortunate to work with the expert coaches at BetterUp (both human and AI) who push me to keep growing.

Some of it even shows up in the data. The psychologist Jer Clifton created the Primals assessment, a measure of the gut-level beliefs you hold about the world, the kind that stay fairly steady across a lifetime. Two of mine moved anyway: I stopped believing the world was dangerous, and started believing it was good. The Ranter era is a low-safety world with enemies everywhere: bad frameworks, worse managers, the drones. I had to fight and prove myself to do anything worthwhile. Over time the world stopped feeling like a fight I had to win and started feeling like a place that was basically on my side.

The Ranter had tied his sense of being right to controlling how everyone else behaved. Somewhere in the last decade I put that bill down. I hold onto what’s mine, the work and the effort and how I treat people, and let go of what isn’t, like whether the world agrees. Being wrong stopped being a wound and became information. The idealism never left. I just stopped turning it into expectations of everyone around me.

The Cleanup Continues

The basement is dry now, but the cleanup continues in the house, and in me. I’m still a work in progress and will be for many years to come. I’m grateful for the chance to look back, and for the people and tools that helped me do the work.

Keep mopping!