What My Son Taught Me About Trying New Things

Let’s be honest: Trying something new can feel risky—especially when failure is a possibility.

But the real risk? Staying stuck because you’re afraid to look imperfect.

But the truth is, being willing to look a little messy on your way to something meaningful is one of the most underrated leadership skills.

What I’m about to share isn’t just a funny parenting moment—it’s a reminder to stop waiting until you feel “ready,” and start celebrating the courage to begin.

You may laugh, but you’ll also walk away with a new perspective on what it means to show up and try.

GET IN THE GAME

Earlier in the spring, I had the chance to coach my two sons’ basketball team.

Now, I’m a huge believer in sports. I think it teaches kids structure, discipline, teamwork—real life skills that go way beyond the scoreboard.

But…Nothing could’ve prepared me for what happened their first game.

Especially with my youngest son.

Let’s just say…He completely ignored the basketball rulebook and everything we had been practicing.

Picture this: We hit the court, the game starts, and within minutes my youngest son is everywhere—double dribbling, running clear across the court (sometimes in the wrong direction), trying to steal the ball from his own teammates, even sprinting through the stands at one point like we were playing tag instead of basketball.

At one point he grabbed the ball, refused to pass it, wouldn’t shoot, just stood there bouncing it with a big grin on his face like he was the main event.

He even took his own timeout to grab popcorn.

It was crazy and very entertaining!

But what got me most wasn’t what happened on the court—it was what happened afterward.

We sat down on the bleachers after the game. I looked at him and asked,“So… how do you think you did out there?”

He paused, raised his eyebrows like he was giving it some serious thought, then broke into a proud little smile and said:“I did good! I dribbled the ball and ran up and down the court! I think I did good!”

He was serious. Genuinely proud. Unbothered. And completely convinced he had an excellent game.

And honestly… I couldn’t stop smiling.

Because in that moment, I realized—This is how we all should think.

When was the last time you tried something new and let yourself celebrate the fact that you showed up?

No pressure to be perfect.No shame in any mistakes or shortcomings you made.No fear of looking silly or messing up in front of others.

Just pure effort. Just the joy of being in the game.

We could all use a little more of that energy.

So this week, I want to remind you:Give yourself permission to try.

To learn something new.To take the shot, even if you travel on the way to the hoop.

You’re not here to get it perfect.You’re here to grow.

WAYS TO TAKE ACTION:

Do something you’ve been avoiding because you’re afraid of not getting it right.

• Start the draft.

• Record the video.

• Make the offer.

• Say yes to the thing that feels new or uncomfortable.

It’s not about perfection—it’s about participation. Celebrate the effort and learn as you go.

REMEMBER: Every master was once a disaster, but they stuck with it and committed themselves to getting better.

You’re not behind. You’re just getting in the game.