Milano–San Remo

What would you do if you knew you would fail, but that failure would lead to real success?

Last Saturday I was watching the 2026 Milano–San Remo, cycling’s longest one-day race at nearly 300 km, when race favorite Tadej Pogačar crashed with more than 30 km to go, and right before a prominent climb.

He hit the ground, lost over a minute to the peloton, and even cracked his frame. For many riders, that would have been the story of the race.

Instead, he got back on his bike, chased down the field, and immediately attacked, splitting the race apart.

By the final kilometers, only one rider could stay with him. They raced into San Remo together, and in a sprint, Pogačar won by half a wheel in a photo finish.

Failure didn’t stop him. The crash didn’t define the race. His response did.

In cycling, even top professionals will crash. In leadership, crashes will happen. Project deadlines slip, deals fall through, and teams unravel at the worst possible moment. What defines high performers isn’t whether they avoid the crash. It’s whether they keep racing to keep the outcome within reach.

At Guiding Flame Academy, our goal is to reframe failure in your own leadership or within your team. I’m always open to a conversation about how to turn setbacks into strategy.