How Caregivers Can Encourage Growth with Calculated Risk Taking

TrueSport

February 1, 2026 | 3 minutes, 11 seconds read

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Encouraging young people to take risks and take ownership of making their own decisions can be hard for caregivers who are used to helping their children avoid failure.

This is understandable and natural, but board-certified family physician and TrueSport Expert Deborah Gilboa, MD, explains that most caregivers are far too risk-adverse and as a result, our athletes actively avoid risk. Unfortunately, that means they don’t have the opportunity to learn from new experiences and failures. We need to allow kids to make decisions and live with the consequences, and Gilboa is sharing the blueprint for how to help your athlete take—and learn from—calculated risks.

See the opportunity in sport-specific risk

When you hear the word ‘risk,’ you may automatically call to mind unsafe behaviors like opting out of a seatbelt or experimenting with illegal drugs. The idea of your athlete making decisions for themselves can leave you wondering if they’ll ‘decide’ whether to obey the curfew you had set. But when she talks about calculated risks and making decisions, Gilboa is referring to risk in a more controlled context, such as taking on a leadership role for the first time or trying a new sport or a new skill. These sport-related risks and decisions may not seem like much, but for a young person, they can be daunting, and they may need you as their caregiver to nudge them into trying something that feels scary.

We don’t develop resilience when everything is going well, Gilboa adds. We grow our resilience muscles when we have setbacks and failures, and an athlete who never takes risks or makes their own decisions will never have the opportunity to test and strengthen their resilience.

Your athlete failing means you’ve succeeded

Gilboa puts it another way: “Caregivers should be looking for more opportunities for their athletes to fail with purpose,” she says. “These failures are essentially a stress test for an athlete’s resilience. We need these small failures and disappointments in order to grow—and experiencing them in a safe environment like sport helps prepare your athlete for the real world.”

“In short, your child is full of short-term goals, but they are your long-term project,” Gilboa says. “And as a long-term project, you have to find opportunities for them to fail, or else they’re never going to learn to handle failure, which is going to be inevitable as they get older. So while it’s hard to watch your athlete go through a struggle, it’s great news for you when they do fail. It means you’re doing your part to help them learn.”

How to help your athlete make risky decisions

When Gilboa talks about risks, she specifically talks about ‘calculated risks.’ A calculated risk simply means that the risk has been assessed: There’s still a chance of failure, but the potential positive or negative consequences have been weighed, and the risk level seems reasonable for the athlete.

“A calculated risk means your athlete is looking at a step-wise progression,” says Gilboa. She likes to use the example of a high dive: If your athlete is new to diving, they won’t immediately go from the lowest diving platform to the highest. They’ll gradually build up, adding complexity to their dives and slowly going higher and higher. The calculated risk isn’t going from the lowest platform to the highest, it’s moving up to a slightly higher platform knowing that there’s a chance that the athlete won’t be able to perfectly execute the dive.

A calculated risk is actually about mitigating the risk, says Gilboa: It’s taking a risk, but breaking it into pieces that are slightly outside of your athlete’s comfort zone.

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TrueSport®, a movement powered by the experience and values of the U.S. Anti-Doping Agency, champions the positive values and life lessons learned through youth sport. TrueSport inspires athletes, coaches, parents, and administrators to change the culture of youth sport through active engagement and thoughtful curriculum based on cornerstone lessons of sportsmanship, character-building, and clean and healthy performance, while also creating leaders across communities through sport.


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