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The Courage to Fail: Learning to Take Risks and Go Down Fighting

“There’s no way I’m leaving vacation early for tennis tryouts,” my 14-year-old daughter Emily said. “I doubt I’ll make the team.” She had just finished 8th grade, but the high school coaches ran JV tryouts in late summer.

“Do you want to be on the team?” I asked.

“I do, but I’ll probably get cut.” Her brother Ben, then 15, looked up from his phone. “Well, you definitely won’t make the team if you don’t try out,” he said.

As a little girl, Emily loved to sing songs for strangers and share stories she “wrote” by stringing random letters together. At least once a day, my husband or I would say to our fearless daughter, “Oh my god, don’t eat that!”

But like many middle schoolers, she’d started to become more cautious and less willing to make mistakes.

We encouraged her to put herself out there—to take risks, to own her goals, and to learn that she could bounce back from disappointment.

Still, I held off on buying plane tickets. I hoped that Emily would reach a decision on her own. But when we were still going in circles several days later, I booked our seats. This did not go over well. I dropped the topic, but then her brother had an epiphany. “You know, you should try out for the varsity team,” he told her. This turned out to be an inflammatory suggestion.

“Are you out of your mind?” Emily asked. “If I’m worried about making JV, why would I try out for varsity?”

Ben explained that kids who are cut from varsity start out higher on the ladder for JV tryouts. “I wish I’d done that,” he said. “I would have ended up on JV anyway, but it’s a smart strategy.” Somehow, he convinced her to tell the coach that she might try out for varsity.

The night before varsity tryouts, the coach emailed the players. Apparently, he had missed the critical word “might” in Emily’s email. She was listed on his roster and was expected to show up the following morning. The coach explained the process; each day, he wrote, the girls could challenge the person directly above them on the ladder. At the end of the week, the top 12 players would make the team.

Emily came downstairs to show me the email, highlighting one data point in particular. “I told you,” she said. “I really am ranked the lowest. Number 25 out of 25 players.

“Look on the bright side,” I said. “You’ve got nowhere to go but up.” I finally got a laugh.

The next morning, I drove her to the school courts and headed to work. She sent her brother a text after she arrived. “Just so you know, I’m going to get crushed,” she wrote. “Go down fighting,” he replied. And then we heard nothing.

When I picked her up that afternoon, she was noticeably calmer. “I beat Number 24,” she said. Over the course of the week, she continued to challenge up. She beat everyone she played, ultimately landing at Number 19. The coach pulled me aside one afternoon. “She had no business beating the other players,” he said. “They’re all technically better, but she fought for every ball. If you keep signing her up for lessons, she won’t have to work so hard.”

Later that day, he cut Emily from varsity, but she didn’t care. She had overcome her fear, accomplished more than she expected, and discovered she was pretty scrappy.

She had found the courage to fail from taking a risk.

She transitioned to JV tryouts and landed the third singles spot. That’s when I finally exhaled. As a parent, it may be harder to push our kids out of their comfort zone than to take risks ourselves.

Phyllis Fagell, LCPC

Phyllis L. Fagell is the counselor at Sheridan School in Washington, D.C. and the author of Middle School Matters (Da Capo Press, forthcoming 2019). She writes columns on parenting and education for the Washington Post.