The Long Way Around

What the road no one would have chosen actually builds

Nobody would have bet on me.

Not my teachers. Not my friends. Not even my family. I was angry, unfocused, and carrying weight I didn’t know how to put down. Nobody was pointing the way — and I wasn’t asking.

The wandering that followed didn’t come from a lack of ambition. It came from a sixteen-year-old trying to work through something he had no tools for, with no one to help him do it. I don’t know if people didn’t notice, didn’t know how, or just didn’t want to be burdened with it. What I know is that I worked through it alone. That takes longer. It leaves marks. And it builds something in you that easier roads don’t.

What it built was this: curiosity, because I had to figure things out without anyone handing me answers. Resilience, because there was no other option. A certain self-sufficiency that looks like confidence from the outside but started as necessity. And yes — scars. The road leaves marks on the way to building you. I won’t pretend otherwise.

Nobody would have put me on the list of people most likely to amount to something. I wouldn’t have argued with them.

THE BEGINNING OF A LONG DRIFT

I took the ACT hungover. Scored accordingly. Decided to go to college about two weeks before it started — not because I had a plan, but because I didn’t have anything better. I finished one year. Then I joined the Navy.

I got lost in some paperwork, had a migraine on the wrong day, and six months later I was out. No drama. No story. Just: suddenly civilian again, completely aimless, with no particular idea of what came next.

I went back to college. Bounced around. Lived with friends. Lived with my grandparents — and God, I am grateful for them. They were the stability I didn’t have anywhere else. Eventually I found something resembling a foundation at a college in Oklahoma City and finished what I’d started.

After graduation came four miserable months at a newspaper. I was, however, the number one TV Guide salesman. I say that without irony. You work with what you’ve got.

Then the mental health field. Then a workover rig in the oilfield. Then a pipeline company. Then a Farmers Co-op in Oklahoma and Nebraska. Nebraska was so boring I came back. Then QA/QC at an environmental engineering firm, opening and closing hazardous waste landfills. I loved that work. The science of it. The field work. The tangible reality of it. I was good at it.

I was also in a rock band. And in a complicated relationship. And still, at some level, trying to figure out who I actually was.

I wasn’t building a resume. I was just trying to find something that fit.

KOREA

I ended up in South Korea. Two years teaching English. I went, I think, because I needed to be somewhere that nothing about me was already decided. In a foreign country where no one knew my history, I could just be a person. Figure things out from scratch.

Korea gave me my wife. That alone would make it worth it. But it also gave me something else — two years of navigating a completely different culture, language, and way of seeing the world. I learned what it means to be genuinely disoriented and find your footing anyway. I learned to read rooms where I couldn’t read the words. I learned that most of what we think is universal is actually just familiar.

We got married. Moved back to the States. Penniless and jobless, both of us. Not a romantic starting point. Temp work. Then a friend made a phone call.

That phone call was for a Safety and Compliance job at a small agricultural insurance company in Oklahoma. 1999. I had no insurance background. I had no particular reason to think I’d be good at it.

It was the beginning of everything.

THE ROAD THAT DIDN’T LOOK LIKE ONE

I moved into Loss Control at that agricultural company. Then my wife graduated college and relocated for her career. We moved with her. I landed in workers compensation doing loss prevention — and started picking up knowledge about industries I’d never formally studied: manufacturing, logistics, construction, healthcare. I absorbed everything.

Then a large specialty carrier. Construction Risk Engineering. I excelled at it. Not because I’d studied construction — because I’d worked in it, literally, from the age of twelve in my family’s HVAC and refrigeration business. I’d been on job sites. I knew what the work actually looked like. I could walk onto a construction site and understand what I was seeing in a way that someone who had only ever underwritten it couldn’t.

They offered me an Inland Marine underwriting position. I took it. More moves followed — construction casualty, back into Inland Marine, a team transition that brought a new company, then another, then another. A decade-plus inside the same market, deepening inside one of the most complex lines in specialty insurance.

Eventually I landed somewhere that felt like the right fit — and in the years that followed, something I couldn’t have predicted happened: the road that looked like wandering turned out to have been building something specific.

The road that looked like wandering turned out to have been building something specific all along.

WHAT THE LONG WAY AROUND ACTUALLY CONSTRUCTS

Here is what I know now that I didn’t know then: breadth, accumulated over time, with real consequence attached to it, becomes a different kind of intelligence than depth alone ever produces.

The person who goes narrow and deep in one lane for thirty years develops genuine expertise. They also develop blind spots the size of a house. They see their problems through one lens — because that’s the only lens they ever picked up.

I picked up a lot of lenses. Environmental QA on hazardous waste sites taught me how contamination moves through systems in ways you can’t see until it’s too late. The oilfield taught me what it means to work in genuinely unforgiving environments where errors have physical consequences. Korea taught me that how you see the world is a product of where you stand — and that standing somewhere else changes everything. The mental health work taught me to sit with people in crisis without trying to fix what can’t be fixed quickly. The band taught me what it feels like to build something you care about and then watch it end.

And twenty-five years of insurance — across agricultural, workers comp, construction casualty, ocean marine, inland marine — taught me that risk is never just a number. It’s a story. And the quality of your judgment depends entirely on how many different kinds of stories you’ve been close enough to read.

That’s not something you can buy. You can’t hire it. You can’t shortcut it. The AI tools that have changed my practice — and they have, genuinely and profoundly — are amplifiers. They make the practitioner faster, more capable, more precise. But they amplify what’s already there. A practitioner with limited experience and a powerful AI tool is a faster version of limited. A practitioner with thirty years of hard-won judgment and the same tool is something else entirely.

AI amplifies what’s already there. A practitioner with limited experience gets faster at being limited. A practitioner with deep judgment gets exponentially more capable.

THE TWILIGHT PROBLEM — AND WHY I REJECT IT

There’s something I’ve said in private that I’ll say here: I found this at the twilight of my career. The ceiling came off, the tools arrived, the thing I’d been building without knowing I was building it finally had an outlet — and I’m closer to the end than the beginning.

I’ve felt that as a loss. Some days I still do.

But here’s what I’ve come to believe: I found it at exactly the right time. Not late. Exactly right.

Ten years earlier, the tools didn’t exist to close the execution gap. The AI capabilities that let me encode twenty-five years of practitioner knowledge into functional systems weren’t there. I would have had the expertise and nothing capable of carrying it at the speed and scale I needed.

Five years earlier, I didn’t have the full body of experience yet. The years that followed — the team, the platform, the responsibility — those years finished something. They were the last few chapters of the story before the story became useful.

The timing isn’t a tragedy. It’s the point.

The long way around is only obvious in retrospect. While you’re on it, it looks like drift. It looks like failure to commit. It looks like the absence of a plan. From the outside, it probably looks like someone who can’t figure out what they want to be when they grow up.

From the inside, eventually, it looks like the only road that could have gotten you here.

The long way around is only obvious in retrospect. While you’re on it, it just looks like the absence of a plan.

WHAT THIS MEANS FOR YOU

If you’ve taken the long way around — if your background is uneven, your path non-linear, your resume harder to explain than most — I want to say something directly to you:

That is not a liability. That is an asset that has not yet been properly valued.

The organizations that will figure out how to use AI well are the ones that pair it with practitioners who’ve seen enough different things to know what they’re looking at. The tool is everywhere now. The judgment to use it well is not.

Your job is not to apologize for the road you took. Your job is to understand what it built — and stop pretending the straight path would have gotten you to the same place.

It wouldn’t have. The lenses you picked up along the way are not incidental to your expertise. They are your expertise.

Nobody would have bet on me at sixteen.

I wouldn’t have either.

But the road knew something we didn’t.

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