Cover Story

Teaching Kids How to Fail  

Whether it’s not making the roster of a sports team at their school, not making the cast of a school play, not making friends, not making the dean’s list or any of the various frustrations in a young person’s life, children need to learn from failure, just as successful adults do. In a new book about failure—which approaches the topic from a child’s perspective—authors Chad and Karen Lilly stress how instead of harming or weakening the character of young people, failure should strengthen it.

The Lillys, who live in the Chicago area, have seen this in raising two children and in the research they have conducted their book, which will be published later this year by Behrman House (title as yet undetermined). The book centers on the profiles of twenty-three famous individuals who encountered failure when young but did not give up, were encouraged by friends and family, and grew to become highly successful in their respective fields later in life.

The authors say their book grew out of the struggles that their now college-age children went through as kids. Karen and Chad were not perfect parents—they learned the book’s lessons from where they failed years ago. “So much failure,” Karen says.

The Lillys offer parents, teachers and anyone who shapes young lives some points of advice for teaching children how to deal with failure:

Don’t be afraid to talk about failure. If a child has failed a test or failed in some other way—even in his or her own imagination—you can be sure it’s already on the child’s mind.

Listen, don’t preach.

Boost their confidence about what they can do, instead of focusing on where they have fallen short. In other words, play to the child’s strengths. If he or she has demonstrated ability in art, but less so in sports, encourage your child to concentrate on his or her proven abilities.

Don’t Criticize, Analyze. Find specific ways in which your child can improve his or her performance. Ask, “What could you do better?”

Don’t set unrealistic goals. Not everyone can be an Olympic champion or an Oscar winner.

Encourage your kids to embrace their inner toddler. Infants naturally stumble and fall when first learning to walk. They pick themselves up and try again, without getting discouraged. Everyone has that inborn adaptability.

Take the long view. Kids often can’t see beyond today, their immediate environment, their school or circle of friends. Talk about the future, which kids can’t necessarily envision when they are discouraged.

Share stories about your own failures. And emphasize the lessons you have learned from your failures. Tell them it’s okay to fail.

Share stories of other people who have failed, picked themselves up, and gone on to success—the focus of the Lillys’ book.

Remember what it was like when you were their age. Speak from a vantage point of maturity, but don’t assume that your child has reached that point yet. Treat your child the way you would want to be treated.

View each child as an individual. Kids aren’t monoliths. Advice that will work for one child won’t necessarily work for another.

Allow your kids to struggle and discover their own solutions. If you do it for them and make things easier, they lose the lesson of the struggle. You can’t walk for your child; she has to do it on her own. Struggles build confidence and self-reliance. Celebrate your child’s effort in overcoming the challenge.


Steve Lipman is a frequent contributor to Jewish Action.

This article was featured in the Spring 2019 issue of Jewish Action.