Leadership on Two Wheels

Ross and I recently returned from what may be the best vacation we’ve ever taken: a cycling trip along the Danube River.

Before this adventure, our longest rides were rarely more than 25 miles. On this trip? We rode at least 25 miles every morning, paused for a relaxed lunch with our 13 fellow cyclists and 4 tour leaders, and then set off again for another long ride in the afternoon. For five days in a row. By the end, we had ridden more than 240 miles.

Near Vienna, Austria

What surprised me most wasn’t the distance—it was the capacity I discovered in myself. I never reached my limit. I could have kept riding. The scenery was breathtaking, the air clean, and my inner sense of peace steady. Even losing our luggage (which spent the week merrily circling Europe without us, arriving just in time for us to return home) couldn’t shake me, thanks to the generosity of new friends who lent us clothes (and hair gel for curls, more importantly).

But what I’ll remember most is the leadership I witnessed on wheels.

The four tour leaders were a masterclass in team dynamics. Each brought unique strengths to the journey:

• one with a gift for artfully arranging snacks at our comfort stops,

• another who noticed when a small adjustment to a bike could improve performance,

• one who smoothed logistical hurdles with calm,

• and another who seemed to know exactly what encouragement each rider needed.

Every morning at the “Route Rap,” laughter burst forth as our tour leaders swapped stories, praised each other’s strengths, and set the tone for the day with the 15 cyclists eager to set off on the day’s adventure.

As I pedaled through castle grounds, vineyards, and riverside villages, I realized: leadership isn’t confined to conference rooms or org charts. It shows up on less-traveled paths, in how we support one another to reach the next bend in the road, and in bringing our strengths to cross the finish line as a team. As the saying goes, if you want to go fast, go alone, but if you want to go far, go together.

This trip gave me more than miles—it gave me a renewed reminder that leadership, at its best, feels like wind at your back.