What I Learned on the Road to Resilience
I was really happy the day in September 2004 when I made it to the top of Massa Marittima on my bike. But a few days earlier, I was a mess.
I had just started a cycling tour through Tuscany. At this point in my fitness journey, I was a Spinning instructor at my gym, but I was still acclimating to pedal clips on the road.
Ciclismo, ink and watercolor by Ian Mutton
On our very first group ride of the trip, I took a tumble and slashed the back of my ankle. By the time we got back to our lodging, blood was seeping through my sock.
The next morning, I was nervous and promptly fell again—this time narrowly escaping the gravelly shoulder and landing in a patch of grass. I got back on the bike and slowly began to rebuild my confidence.
The photo below was taken after a grueling 7 km climb up a winding hill to a classic Italian village. I initially thought I'd be taking the sag wagon, but with a group of supportive peers riding by my side, we made it to the top together. It felt great, and the pasta we ate in town refueled my body and my spirit.
I thought I had falling licked. Until our last day.
Drafting on a flat road in a paceline of 20 riders, we came to a stop sign. I couldn't get my shoe unclipped from the pedal and fell again. It was the universe's way of saying, "Don't get too cocky, missy."
This was a lesson that I took to heart: Be humble and persevere. I may have fallen three times, but I always got back up.
It remains one of the best vacations I've ever taken—not only because of the great food, scenery, and camaraderie. But because it challenged me to challenge my fear, to expand into my growth edges. Sure, I embarrassed myself by falling. But I made myself proud because I got up and tried again.
Right now, many purpose-driven leaders are navigating winding climbs, unexpected tumbles, and moments when we feel like taking the sag wagon would be the easier choice. The road ahead is uncertain, and just when we think we’ve figured it out, something new challenges our balance.
As a person who’s been in the CEO seat and now supports CEOs, I hope it provides some relief when I say your job isn’t to avoid falling. It’s to learn how to fall without giving up.
The lessons I gleaned about resilience on that cycling trip apply to leadership, too.
Your first fall stings. Whether it’s a failed funding initiative, a difficult board meeting, or a strategy that didn’t pan out, setbacks happen. It’s OK to be frustrated. Feel the pain in that moment, then move on to the next best step.
Support matters. Just like the peers who rode by my side, leadership isn’t a solo sport. Surround yourself with people who remind you that you can keep going, even when the road gets steep.
Success doesn’t mean you’ve "arrived." Sometimes when you’re sure you’re on the right path, another detour will come your way. Stay humble. Stay adaptable. Keep learning.
This moment—whatever climb you're facing—isn’t about whether you stumble. It’s about whether you get back on the bike. And the leaders who do? They’re the ones who build real, lasting impact.
If you need support on your leadership journey, I invite you to explore our services and see how we can help.