CEO Coaching: Fly Rods, Drug Boats, and Leadership Lessons

Lessons from Xcalak

Years ago, an orthopedic surgeon (with whom I had the misfortune of spending far too much time) told me not to do something. Naturally, I did it anyway: hunt bonefish in saltwater with a fly rod. As he warned, it only takes one good hit to get hooked for life.

I just got back from a trip to Xcalak—a tiny speck on the map near the Mexico-Belize border—and as I replayed the highlights (and lowlights), I realized: chasing bonefish has a lot in common with leadership. (Last year, I wrote about fly fishing in Cuba, so maybe this is becoming a series. You’re welcome.)

Here we go.

Wonderful Things Exist in Dark Places

The fishing was fantastic. The tiny lodge was charming. The community? Dirt-poor, and the cocaine trade is booming. Locals cruise the beach in battered boats, searching for kilos dumped by Colombian traffickers—apparently Mother Earth makes a fine shipping route.

It was disheartening. But also oddly familiar. Some of my best adventures—in life and in business—have come from less-than-glamorous environments. Sometimes, you’ve got to go where others won’t. That’s where the magic hides.

Cast. And Cast. And Cast Some More.

Catching fish takes work. You cast hundreds of times. Maybe a few fish follow. One eats. If you’re lucky, it makes it to the boat. Patience and persistence are essential—but so is knowing your environment. Fishing in dead water? You’re wasting your time.

Same goes for business. Are you marketing to people who actually care? Asking the right questions to the right people? Are you taking enough reps in order to be successful or are you afraid of failure?

The Guide From Hell Still Taught Me Something

One of our guides was a total tyrant. Imagine casting into a 25 MPH crosswind while he barked orders like a drill sergeant with a sunburn. Not exactly the Zen fly fishing experience I was hoping for.

I told our host I wouldn’t fish with him again—but I still learned a few things. That’s the trick in business, too: you’ll meet difficult people. You can let them wreck your day, or you can squeeze value out of the situation and move on with your blood pressure intact.

Enthusiasm Is Good. Chill the F*** Out Is Better.

When you only get a couple shots a day at the fish you’re targeting, it’s easy to get overhyped and completely blow it. (Ask me how I know.)

More reps help. So does talking yourself down off the ledge. If you want to get better at something—fishing, leadership, public speaking, whatever—practice and self-regulation go a long way. As my friend said to me, “Calm the f*** down. Then cast.”

Everyone Has a “Better” Way

Every guide had their own technique, and each insisted theirs was gospel. Yesterday’s hero move? Suddenly “all wrong.” I’ve learned to listen first—even when I’m pretty sure they’re wrong—and adapt as needed. (Pro tip: If you want to tick off a guide fast, act like you know everything.)

Same in business. Try new methods. Be flexible. You’ll eventually refine your own style—but don’t be the know-it-all who misses the fish because you refused to try something different.

If you’ve been reading my blog for a while, you know I love pulling leadership lessons from everyday life. You don’t have to stand in saltwater to find insight (though, seriously, you should ignore my doctor’s orders and try it).

Every day gives us material—if we bother to reflect. So tonight, give yourself 10 minutes. What did today teach you?