Sunday Bikes and Leadership Vibes

Sunday Bikes & Leadership Vibes: A Lesson from the Driveway

This past Sunday was supposed to be just another “burn off the boys’ energy” kind of Sunday: park, basketball, and maybe a bike ride. Instead, it turned into one of the best leadership lessons I’ve had in a long time.

First, my 9-year-old asked to try his mom’s Trek. It was his first time on an adult bike. I braced myself for wobbling and mini-crashes, but he rode off like he’d been doing it for years.

Then came my 5-year-old, “Can you take off my training wheels?”

I hesitated. Honestly, I didn’t think he was ready until next Summer. I told him no. But he asked again politely, determined, eyes locked on the goal.

So I took them off. He hopped on, a little shaky, tried both pedals at once, and lost balance. I coached him: “One pedal at a time.” Second effort, he was off around the block with no support, no holding the seat, no coaching shoutouts. He even made a slow, controlled stop like a seasoned rider.

In that moment, I realized I was the one who wasn’t ready. I underestimated them both. I used last year’s “successful method” with my older son and assumed it should apply to my younger. Success formulas don’t always translate to new people, new contexts, or new moments.

Leadership reminder:

Every person learns differently. Every person listens differently. Every person moves at their own pace, with their own strengths, fears, and motivations. When we rely too heavily on past success, we risk capping someone else’s growth. What unlocked their progress wasn’t my coaching. It was giving them space to try.

Their proud smiles said it all because they owned their success. The only thing they thanked me for was, “Thanks for letting us try.” That one line hit hard.

Sometimes people don’t need us to lead from the front—they just need us to remove the metaphorical training wheels.

Leadership takeaway for the workplace:

If we want teams to grow, innovate, and surprise us, we have to create more moments where people can try, test, explore, and even wobble a little without fear.

So here’s the real question:

How do we create this “training-wheels-off” feeling at work?

Is it giving people stretch assignments?

Letting them own projects end-to-end?

Asking before assuming?

Creating a safe space for trial and error?

I’d love to hear what’s worked in your teams. How do you empower people to prove (even to themselves) what they’re capable of?