Curious, Not Certain: Why Curiosity Will Always Outlast Expertise

A story about how curiosity, not confidence, built my career. And how I found the willingness to ask again is what moves you forward.

The first time I walked into a radio station, I wasn’t chasing a job. I was running. Running away from chaos and dysfunction, in search of safety and stillness.

I was 16, coming from a home that was, on its best days, unpredictable. On the worst days, it was something else entirely. Loud voices. Quick tempers. Emotional ambushes that made stillness feel like luxury. A radio station became my refuge. A place where the outside noise couldn’t reach. The blinking lights, the hum of the boards, the low conversations behind studio glass, all of it made sense to me in a way nothing else did.

My teenage years were spent in a coyote costume. That was the gig, the radio station mascot, Cody the Coyote, the famed pet of KEBC in Oklahoma City. Putting aside the smell of the fur, and the foamed head sweat bands, it got me in the building. Once I was there, I never wanted to leave. I volunteered for every job, no matter what, just to stay longer. I asked so many questions, I’m sure they wanted to duct tape my mouth by week three. However, I kept showing up. Not because I had a plan, I didn’t. But because I had questions. And at the time, questions were the only thing I had more of than fear of being at home.

I didn’t know it then, but that instinct to be curious instead of scared saved me. Not just then, but repeatedly to this day.

Curiosity was the only way forward.

When you grow up with instability, you learn two things early: one, nothing is guaranteed; and two, you'd better figure it out fast. That urgency didn’t leave me. But instead of calcifying into control or certainty, it turned into a drive to learn.

Fresh out of the coyote suit, holding down airshifts

At the station, KEBC to be exact, I taught myself how transmitters worked. How microwave antennas bounce signals off towers. How to edit tape with grease pencil marks and a razor blade. Later, how music logs were assembled, spots rotated, and how rotations influenced audience behavior.

With the introduction of computer programs, automation, and the technological revolution in radio, I became a sponge, not out of ambition but necessity.

Curiosity became my safety net. Over time, it became my superpower.

That pattern showed up again when I became a corporate programmer for CBS/Infinity Broadcasting. I didn’t know how to manage a profit and loss (P&L) statement or build a strategic budget. So I dove into business books as if they were survival guides (Survival guides and instinct are skills that every Eagle Scout knows).

Mom, Dad, I, and my Eagle ceremony.

I sat with finance teams. I asked the dumb questions. I learned by watching how smart people explained complex ideas to people who weren’t supposed to get it. Then came the next leap.

He’s GONE Public

August 2003. Fareed Suleman, former CFO of Infinity, asked me to leave my high-profile job at CBS and join Citadel Broadcasting, where he partnered with Teddy Fortsman. Farid was the CEO, and I was the President of Programming. It was a smaller company, but its economic mission was clear: to take it public.

I looked him in the eye and said, “I’ll do it. One condition, only if you teach me how to run a public.” He did.

I learned the art of roadshows. How to write guidance. What “materiality” meant when speaking to Wall Street. I read 10-Ks and 8-Ks like they were thrillers. I asked what EBITDA actually measured. I didn’t pretend to know. I made it clear I wanted to learn.

One of many bad hairstyles over the years

And that moment, standing at the New York Stock Exchange, that August, when we took the company public, it was a full-circle reminder that curiosity can carry you places certainty never will.

Reflecting back, I now see that each chapter started the same way early in my career: with the quiet voice inside that said, I don’t know how to do this… yet.

Now, REALLY Listen

The need to really learn and listen was on full display the moment I walked into Harpo.

Here I was, a radio guy dropped into the most legendary television production house in the world, surrounded by people who had been there longer than I had been in the business. The Oprah Winfrey Show wasn’t just a TV show, it was a cultural force. And, I wasn’t just the new guy, I was the guy from another medium entirely.

It was immediately clear I wasn’t going to impress anyone with what I already knew. So, I didn’t try. Instead, I chose to do the only thing that’s ever worked for me when I’m out of my depth: I stayed curious.

I asked questions. I listened in meetings like they were sermons. I shadowed producers, studied scripts, watched edits, and soaked up every bit of information I could. Because if I was going to be of any use at all, I first had to understand the room. And to understand, I had to shut up and learn.

What started as survival turned into one of the greatest learning arcs of my life. It didn’t just prepare me for the OWN turnaround; it humbled me. It taught me that even after decades of success, reinvention is possible.

If you’re willing to drop what you think you know, lean all the way into curiosity.

Understanding vs. Answering

There’s a big difference between asking a question and being curious. A question wants an answer, where curiosity wants a journey. And those aren’t the same thing.

Today, people aren’t reading entire books as much as they used to. I see all the time offers and people telling me they’re watching summaries of books on YouTube or using companies that offer executive book reviews. We’re losing the mindshare battle where people are not reading full articles too; we’re reposting carousels from someone who did.

Now, there is nothing wrong with distillation; in fact it’s something I’m actually pretty good at. But if that’s all we do, we end up with shallow expertise and hollow leadership.

I’ve been there. I’ve been the guy who wanted to look smart. Who answered fast. Who didn’t want to admit he didn’t know something? And you know what crept in when I did that? Imposter syndrome. Every time.

Sitting in rooms with people who had more degrees than a thermometer made me feel small. I wore the suit, trying to project an image of confidence that was bigger than who I really was. My insecurity might as well have been pinned to my lapel like a “Hello, My Name Is” sticker.

Beneath it all, I was terrified someone would figure me out. That they’d see I didn’t belong. The mental trap of that thinking was paralyzing. But curiosity became my way out. It was the key that unlocked the emotional maze I’d built for myself. When I sense the specter of Imposter Syndrome looming, I unplug and reflect on what I need to learn.

Because the moment you begin listening, being curious, and start doing the work of learning, the feelings of confidence flow in.

Lean into the feelings of “You DO belong here.” When you do, suddenly, all the ground underneath you gets firmer. You can feel it. Everyone can.

Stay Curious, My Friend

If you're going to stay curious, you have to fight for depth. That means reading long-form when your brain wants bullet points. That means sitting with the weird idea that doesn’t have an immediate application. That means putting yourself in rooms where you’re not the expert. Or better yet, rooms you don’t want to be in, actually to listen.

The people I admire most aren’t just high performers. They’re deep thinkers. They take notes. They ask questions. And they permit themselves to slow down long enough to understand what they’re learning.

These are for you. Write down what pops into your head:

• When’s the last time you were bad at something… on purpose?

• When’s the last time you followed a hunch, not a strategy?

• What’s something you’ve always wanted to try, but never permitted yourself to explore?

Because if there’s one thing I’ve learned about staying relevant, connected, and creatively alive, it’s that you don’t thrive by knowing more, you thrive by being curious enough to ask again.

So the next time something sparks your interest, whether it's a headline, a podcast, a passing comment, or the desire to pick up an instrument: STOP.

Write it down, and follow that thought. Whatever it is, large or small, start the thing. Do it because you felt something, and you may find that ‘feeling’ is the start of something real.

And in the words of the most interesting man in the world, “Stay Curious, My Friend.”