A Well-Lit Path: A Blog from Westtown School

Winning through Failure: Four Ways to Help Your Teen Learn by Losing

Posted by Linda Rosenberg McGuire on April 1, 2015

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Winning_through_failureMany parents today are putting in overtime hours to make sure their teenager never experiences academic failure, but to what end? 

Exhausted working parents are running around Staples late at night grabbing poster board and glue stick for a forgotten project, or spending hours trying to squeeze the best possible homework out of their child.  Moms and dads are allowing for “sick days” so their teenager doesn’t have to take a test they are unprepared for, hiring tutors to serve as homework wardens, and dissuading their teens from taking classes they may not get an A in.

I am not convinced failure is to be avoided at all costs. In fact, I see lifelong benefits in experiencing and then recovering from, failure. Here are four that come to mind:

  1. Failure often provides a unique learning opportunity for your teen. Maybe it is as simple as learning to write down all of their assignments or to plan in advance.  Perhaps they learn that too much stress leads to forgetfulness, or that calculus isn’t quite as intuitive as basic computation. In all cases, it becomes their lesson to learn from experience rather than our lesson to try to teach them.
  2. We can all agree that resilience is an important quality. Success may feel fantastic, but it does little to teach your teenagers that they can and will recover emotional equanimity after a setback. Working through the feelings that a failure provides teaches your teen about the arc of emotions that accompany disappointment in oneself or in an outcome. The sting and discomfort is mitigated by time, and your teenager learns that they have the resources within to face up to their own struggles, whether self-inflicted or not. Once developed and utilized, these resources are the building blocks of resilience and grit.
  3. As your teenager matures, it is important that they begin to understand what their strengths and weaknesses are. Typically, self-knowledge is gained through direct experience, not instruction.  If there is no allowance for potential failure, it can become challenging for your teenager to have a realistic understanding of where they genuinely may need extra help, either with academic areas like mathematics or language, or with executive functioning like organization or consistent motivation.
  4. Most, if not all, teachers have a story about the student who was devastated the first time they did not get all As or a perfect score. Always expecting perfection is not only unrealistic but burdensome.  If your teenager is one of those exceptionally stellar students, practicing “not being the best at everything” may be an important component of reducing perfectionism and all the unreasonable demands, and unrelenting stress, which goes along with it. Students who have only experienced the very best grades can struggle in college when they are faced with more demanding classes and other high-achieving students. Learning to survive less than perfection can be a key element in college success.

All of us want the very best for our children, and therefore valuing failure may seem counter intuitive. However, the “very best” probably includes lessons learned, resilience, self-knowledge and the minimization of unrealistic standards. I suggest thinking twice before rescuing your teenager from a potential failure because they may be missing out on a valuable experience. Furthermore, encouraging a high-flying student to pursue a subject they may not excel in can help pave the way for the challenges, set-backs, and failures that are ultimately inevitable.


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Topics: Raising Resilient, Healthy Teens

Linda Rosenberg McGuire

Written by Linda Rosenberg McGuire

Linda Rosenberg McGuire was the Dean of Students at Westtown School from 2011 until 2018. She is a parenting coach, consultant, speaker, and avid writer, providing insight, support, and education for parents and teachers who live and work with teenagers. She works with schools to inspire and reinvigorate their faculty to work successfully with even the most challenging students. Linda is passionate about helping parents develop more effective relationships with their teenagers, stressing the importance of listening, limit-setting, and building competence, character, and independence. Linda has 30 years of experience working with children, most of that time focused on parent-teen relationships. Linda began her career as a caseworker and trip leader for teens-at-risk, leading to work as a community mental health therapist and a school-based counselor. For the past 12 years Linda has been employed in independent school administration, working with teenagers, parents, and faculty as a program director and a dean.Linda received her BA from Bowdoin College, her MSW from the University of New England, and her Master of Organizational Leadership from Nichols College.