What a 290 KM Ride Taught Me About Leadership and Endurance

On the weekend of October 18th and 19th, I pushed myself to the edge, not in a boardroom, but on a bike. I cycled virtually from Milan to San Remo, a 290.73 km route known as La Primavera, the world’s longest one-day professional cycling race. It took me 13 hours and 28 minutes to complete, with over 1,856 meters of ascent.

As both a Chief Financial Officer (CFO) and an amateur triathlete, I’ve long believed that sport has something important to teach us about business. And after this ride, I’m more convinced than ever.

This wasn’t a random challenge. Italy is, and always will be, my second home, and Milan, where the route begins, is where I lived five of the happiest years of my life. That made this challenge feel personal and the timing wasn’t by chance either. As a passionate cycling fan, I had been thinking about riding La Primavera for a while, but when the Portuguese cyclist, João Almeida, won a mountain stage at Angliru (one of the most demanding climbs in the sport) with absolute mastery, something clicked with his victory inspiring me to finally go for it.

It also happened to fall on the same day as the Ironman Cascais. While I wasn’t physically there, this ride became my way of joining in spirit with everyone taking on their own long-distance battles that day. One day, I hope to take on that Ironman myself and this ride felt like a step in that direction.

Here’s what it taught me about resilience, adaptability, and consistency, and why these aren’t just personal values, but essential professional ones.

Resilience: Don’t Quit When It Hurts Most

Around the 200 km mark, my energy was nearly gone. I’d been riding for hours, and the temptation to stop was real but this is where resilience lives, when everything in you says “this is enough” and you keep going anyway.

It reminded me that progress, whether physical or professional, doesn’t always feel good. In business, we all face our climbs, missed goals, tough quarters, shifting strategies. And often, the difference between success and failure is the ability to keep pedalling through the pain.

That moment on the bike brought that lesson home. Resilience isn’t about being unaffected. It’s about not giving up when things get uncomfortable or downright brutal.

Planning vs. Adaptability: Prepare Well, Adjust Faster

For a 290 km ride, preparation is non-negotiable. I trained for months. I mapped out pacing strategies, nutrition, hydration - the whole thing. You simply can’t get through 13+ hours of cycling without a plan.

But even the best plans meet reality: unexpected fatigue, sudden dips in energy. That’s when I realised planning alone wasn’t enough, I had to adapt and listen to what my body was telling me, not just what the schedule said.

The same is true at work. We need solid strategies but we also need the agility to adjust. Because reality doesn’t always follow the script, and staying rigid in the face of change rarely ends well.

Consistency: The Power of Small, Sustained Effort

You don’t just show up one day and cycle 290 km. That distance is the product of consistent training, small improvements, and showing up again and again, even when it’s hard.

During the ride, I didn’t sprint nor didn’t make drastic moves. I focused on holding a steady pace, pedal stroke by pedal stroke, because that’s what builds endurance. That’s what gets you through.

Professionally, I’ve seen the same principle at play. It’s not always the big initiatives or bold changes that move us forward. It’s the consistent, often invisible actions, like trusting the process, following through or supporting the team, that generate real momentum. Over time, consistency builds trust, and that trust is the backbone of both strong teams and long rides.

Back at the Desk, but with a Different Lens

I returned to my desk sore, yes, but also with renewed clarity.

This wasn’t just a physical milestone. It was a reminder that the qualities we lean on to complete something as gruelling as this ride are the same ones that help us navigate complex business environments, like resilience to move through setbacks, planning, paired with adaptability, and a steady commitment to consistent effort.

What felt, at times, like an impossible personal challenge ended up reinforcing the very leadership behaviours I try to bring to work every day.