Prince Charles—now King Charles—slapped my knee and laughed.

“Exactly. That is what I would like to see.”

I was sitting in Clarence House, his London residence, in the final stages of an interview for a major leadership role with the Prince’s Foundation. I had already made it through multiple rounds of conversations, and now I was face-to-face with the future King of England.

“It’s better to shoot for a star in the sky and miss than a toad in the road and hit.”

We were talking about leadership, risk-taking, and how to inspire a team. And that’s when I dropped one of my mom’s classic pieces of wisdom:

That was one of my mom, Gini Barnes’, many homespun sayings—words that sounded odd at first but stuck with you for years. And this one? This one shaped the way I think about risk, ambition, and stepping outside of my comfort zone.

A. photo from my first time meeting with Prince Charles, now King Charles, during the Seaside/Pienza Institute’s visit to Highgrove. That’s me on the far right standing next to my good friend and colleague, Dan Slone.

The Safe Path Leads Nowhere

At some point in life, you’ve probably faced a choice between taking a big swing or playing it safe. Maybe it was a job opportunity, a new business idea, or a move to a new city. There was the “safe” choice—one with low risk but also low reward—and the “big” choice, the one that excited you but also made your stomach turn.

Shooting for the toad in the road is easy. It’s low-hanging fruit, a sure bet. But what do you get for it? A squashed toad. Nothing meaningful.

Shooting for the star, though? That’s where things get interesting.

My Shot at the Stars

When I got the call about the COO position for PF Urban, the for-profit arm of the Prince’s Foundation, it was one of those moments. I was in a solid position in my career, but this was different. This was an opportunity to lead a team within an organization tied to the British monarchy.

The interview process was intense. There were rounds of meetings, long discussions about my experience with projects like Disney’s Celebration, Florida, and I’On in Mount Pleasant, South Carolina. And then, there I was, sitting across from Prince Charles himself.

We talked about leadership, vision, and motivating people. When he asked how I would inspire a team, I leaned on my mom’s words. “It’s better to shoot for a star in the sky and miss than a toad in the road and hit.”

I didn’t get the job.

A UK-based candidate who was already working with the foundation ultimately got it. But here’s the thing—taking the shot still changed me.

I walked away from that experience with an incredible story, new insights, and a reinforced belief in taking risks. I met fascinating people. I got a glimpse into a world I wouldn’t have otherwise seen. And none of that would have happened if I had decided it wasn’t worth the effort.

Your Shot Is Coming

Right now, you might be standing at a crossroads. A job opportunity, a big move, an idea you’ve been sitting on. It’s scary, right? The possibility of missing. The possibility of failure.

But ask yourself this—what’s the worst that could happen? And more importantly, what’s the best?

Because even if you shoot for the stars and miss, you’re still pushing forward. You’re still learning, growing, and opening doors you never even knew existed. But if you keep aiming low, keep playing it safe, you might wake up one day realizing you never really moved at all.

So take the shot.

Go for the star.

And if you miss? At least you didn’t waste your time on a toad.

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