“Your keynote was so much fun, and funny!”
I hear some version of that often while signing books after a presentation. I love hearing it. Few people know the humor started with a dare I gave myself many years ago.
A Dare in the Park
I was at the park with my dog on a Sunday morning, throwing a ball, when a question popped into my head.
If I died right now, what would I regret never having tried?
My first thought surprised me. Stand-up comedy.
Really? Not climbing a mountain or learning another language? Apparently my deepest concern was whether strangers would laugh at my jokes and stories.
My dog had a simpler priority. Throw the ball again.
At first I thought the idea was silly. Surely there had to be something else. But I sat with that question for hours, and stand-up kept coming back. By Monday, I was onstage at an open mic, holding a microphone and delivering a 15-minute comedy set.
There’s a big difference between thinking you’re funny in a park and asking a room full of strangers to agree.
Listen to the Crowd
The crowd was gracious. When I finished, I felt an enormous sense of relief.
Well, I thought, I did it. Never doing that again.
Then a seasoned comedian stopped me as I walked offstage. “That was a great set!”
I looked at him with considerable doubt. I figured he was being kind to the new guy.
“Listen to the crowd,” he said.
Until that moment, I hadn’t noticed. People were cheering and calling out, “Bring him back!” My plan to retire after one performance needed revision.
That encouragement turned into a year of open mics. I even got paid for a few shows. Those nights taught me how to read a room, embrace silence, adjust quickly, and recover when a joke didn’t land.
And trust me, some of them did not land. A joke that sounds brilliant at home can meet an audience with a very different opinion.
Eventually I stepped away from stand-up. When people ask why, I tell them the truth. I was the only one standing up.
Why Humor Belongs in Serious Rooms
I don’t consider myself a comedian. I’m a keynote speaker who understands the power of humor.
Leadership, teamwork, and change are serious topics. They affect people’s livelihoods, relationships, and futures. But serious ideas don’t always need a serious delivery.
When people laugh, they relax. When they relax, they listen. When they listen, they learn. And when they learn while having fun, they’re far more likely to remember the message and act on it.
You can see it happen in a room. Shoulders drop. People lean in. A room full of individuals starts to feel like a group sharing an experience.
A funny story often opens the door to an idea. People recognize themselves, laugh, and become more willing to look at a habit or try a different approach.
And leadership gives us plenty of material. We make plans, get distracted, avoid difficult conversations, and occasionally hold a meeting to discuss why we have so many meetings.
We might as well learn while we laugh.
My goal is for people to leave thinking differently and ready to take action. If they laugh along the way, even better.
Looking back, I’m glad I listened to that persistent thought in the park. What started as a personal dare became a lasting part of how I connect with audiences.
So let me pass the dare along. You don’t have to turn it into a career. You don’t even have to be good at it. You only have to be willing to try it once.
What’s something you’ve wanted to try but keep talking yourself out of?