⛰️ Trail & Error: A Liberal Arts Life

Welcome to Trail & Error— on building a resilient, meaningful life and career, especially if you’re stepping off the traditional path. Sometimes it’s coaching insights. Sometimes personal stories. Always honest, always a little unfinished.

We’re about six months in and closing in on 150 subscribers—huge thanks to all of you who’ve been here from the start. I wouldn’t be doing this without you.

This week’s topic: what it means to live a liberal arts life.

Curious what that means? Read on 👇

I want to live a “liberal arts life”

Last week, someone I was coaching described what they really wanted.

Not to retire early.
Not to scale a business.
Not to quit work entirely.

They just said, “I want to live a liberal arts life.”

It clicked immediately.

A liberal arts life isn’t about avoiding work—it’s about expanding life. It’s about staying curious, learning for the sake of learning, doing useful things across domains, and engaging with the world through many lenses, not just a job title.

It’s a life made up of projects, not just promotions.
Of purpose, not just productivity.
Of making sense of things, not just making money.

And it reminded me: that’s what I’ve been trying to build, too.

I was raised by two nonconformists who modeled this long before I had language for it. (Hi mom, hi dad! 👋)

They’re both still working well into their 70s—not because they need the money, but because they’re still pulled by something deeper.

Service. Curiosity. The joy of making things better.

It’s never been about recognition or income for them.
It’s been about being useful in the fullest sense of the word.

Same here. I didn’t go into tech to strike it rich. I went in because the internet was growing fast and I wanted to be part of the learning curve. To contribute something, to feel inside of it.

Before that, I studied history at Dartmouth. Not because I wanted to become a historian, but because I wanted to understand the arc of things. To wrestle with questions that don’t have clear answers. To become more whole.

Even later—when I left a job I liked just after my son was born—it wasn’t a rejection of work. It was a move toward alignment. I knew I couldn’t keep climbing the middle management ladder and be the kind of dad I wanted to be.

And now? I guess I’m still building that liberal arts life.

Some days it feels a little blurry.
Some days I wonder if I should be more focused, more linear, more “optimized.”

But then I talk to someone who names what I’ve been chasing all along—and it feels like home.

A liberal arts life isn’t a detour.
It’s the destination, for those of us who choose it.

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If this resonates, I’d love to hear your version of a “liberal arts life.”
What does it look like for you? What does it include?

Hit reply or send me a DM. I read every one.