On Curiosity as a Career Strategy

The best career advice I ever ignored was to “pick a lane.”

I didn’t ignore it on purpose. I just never had a lane to pick. What I had was curiosity. An almost compulsive need to understand how things work, why they break, and what happens when you take them apart. That instinct has driven every major decision in my career, starting with one that had nothing to do with technology at all.

The punk

I was a punk when I was younger. A straight-up punk. Terrible mouth, very antagonistic, got into a lot of fights and trouble. Lost more than I won.

My dad died a few years before I graduated high school. I hadn’t had the time to mourn or deal with any of it. Once he was gone, my mom and I moved from Indiana to Rhode Island. I’d moved around a lot as a kid, so the relocation wasn’t the hard part. I’ve always been good at making friends. The hard part was trying to manage a new school, new social structures, one parent, and a 25-hour-a-week job all at once.

I was the stereotypical smart slacker. Abysmal grades, but I did well on standardized tests and had this extensive collection of weird knowledge. I knew college wasn’t for me. Not because I couldn’t do the work, but because I couldn’t sit still long enough to pretend I cared about a curriculum someone else designed.

So when I graduated, I slipped into a funk. For the first time in my life, I had space to process everything I’d been outrunning. I spent about a year doing light web design work. Scraping by. No direction. Just existing.

The recruiter

My best friend had graduated a year behind me and was joining the Air Force. He saw what I was doing. Or more importantly, what I wasn’t doing. He made me go see his recruiter.

I was genuinely curious. Not sold. Not inspired. Just curious.

Everything about the process pulled me in. The language, the nomenclature, the structure. It was all new, and new is the thing that has always focused me. When everything else in my life was noise, something unfamiliar and interesting was the signal.

I ended up enlisting. And I didn’t pick computers. I didn’t pick technology. I picked EOD. Explosive Ordnance Disposal. Bombs and ordnance. Because that was the thing that made my brain light up. It was dangerous, technical, required precision, and nobody in my life would have predicted it. That’s exactly why it worked.

The pattern

That first decision set the pattern for everything that followed. I didn’t plan a career in technology. I followed where my mind wanted to go, and my mind wanted to go wherever the interesting problems were.

From EOD I moved into combat communications. From there, network architecture. Then data centers, storage, cloud infrastructure, systems engineering, management. Along the way I ran a whiskey education business for fifteen years. Not because it was strategic, but because I got curious about spirits and couldn’t stop until I understood the industry.

Every one of those detours taught me something the straight path never would have. EOD taught me how to stay calm when the stakes are real. Combat comms taught me how to build something that works when nothing around you does. Whiskey taught me how to talk to people who don’t care about technology. Which turns out to be most people.

The person sitting in the VP chair today isn’t here in spite of the detours. He’s here because of them.

The advice

People will tell you to pick a lane. They’ll tell you to specialize, to focus, to build a linear narrative that makes sense on a resume. For some people, that’s the right move.

But if you’re wired like me. If your brain won’t let you stay in one place. If you keep getting pulled toward the next interesting thing. Stop fighting it. That’s not a bug. That’s the feature.

Curiosity isn’t a distraction from your career. It’s the engine of it.

Every lateral move, every weird detour, every time you followed an instinct that didn’t make sense to anyone else. That’s all compounding. You just can’t see it until you look back.

I went from being a punk with no direction to leading technology strategy for a company where 70% of the team are engineers. Not because I had a plan. Because I had questions, and I never stopped following them.