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No Regret: How to Train Yourself to Take Risks

Leave it all on the course by practicing your ability to be bold.

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Substitute the word “triathlon” for “life” in writer Hunter S. Thompson’s famous quote: “Life should not be a journey to the grave with the intention of arriving safely in a pretty and well-preserved body, but rather to skid in broadside in a cloud of smoke, thoroughly used up, totally worn out, and loudly proclaiming ‘Wow! What a ride!’”

Playing it safe in competition is most athletes’ biggest regret. Even big moves that end in a crash-and-burn don’t elicit as much regret as finishing a race “in a pretty and well-preserved body.” Even so, safe racing strategies are the default. If you don’t practice being bold—going with a break, ratcheting up the pace when you start to feel fatigued—it probably won’t happen in a race situation.

Practice under pressure

“Practice under pressure” is Dr. Allie Wagener’s first suggestion. Wagener is a clinical psychologist with Premier Sport Psychology in Edina, Minnesota. “You’re most likely to hang back in a high-pressure situation—like the middle of an important race. So, build those situations into your training and challenge yourself to take risks when the stakes are not that high—a time trial with your training partners; a local 5K race; a once-a-week session with a faster swimmer or a more advanced cycling group. In training, you often settle into a comfortable, get-it-done pace. Practice responding aggressively so it becomes more natural.”

Surging or covering a training buddy’s move not only paves that risk-taking mental pathway, Wagener says, it provides you with data on what really is a reasonable risk. If six out of 10 times you were able to sustain a 5:45 per mile running pace in training, going with that pace in a race is a reasonable risk.

Know what you’re after

Second, set specific, meaningful goals, even in training sessions. “Being bold is vague and therefore hard to accomplish,” Wagener says. “Set specific goals: ‘I’m going to pass three people at the end of this 5K,’ or, ‘I’m going to start out at the front of the pack instead of the back.’ You’ll achieve specific instances of being bold and start to see yourself as a risk taker.”

Focusing on feelings makes you more likely to dial it back. “Instead of, ‘I’m tired, and I need to slow down,’ think, ‘I’m tired, and I’m going to pick up my pace,’” Wagener suggests. “Acknowledge the feeling but shift your focus to your goal of being more aggressive.”

Embrace failure

And finally, the hard truth that Hunter S. Thompson didn’t come right out and say, is that going for it in life and in triathlon assumes some failure, and that’s never going to feel good in the moment.

“We tend to see failure as bad, something to be avoided,” Wagener says. “Instead of avoiding failure altogether, you need to practice your response to it. Of course, you’ll be disappointed in the moment if a big move doesn’t yield positive results, but understand that failure is part of competition, no one succeeds all the time, and the outcome of one race or training session doesn’t define you. Celebrate your boldness, distinct from the outcome (e.g., “I went with the leaders when the break happened.”), and use failure as an opportunity for growth.” Just don’t forget to loudly proclaim, “Wow! What a ride!”

This article originally appeared in the December 2018 print issue of Triathlete magazine.