Why I\’m Teaching My Kid All About Failure

portrait of jenny mollen in front of brick exterior

Up until my son Sid was 5, his life was filled with flattery and validation for every endeavor he embarked upon. His artwork was likened to that of Basquiat, his dancing naked in the living room applauded as if he were Baryshnikov. Like so many parents, I’d indulged him and adored him and convinced him that there was nothing he could not do.

As a result, Sid decided that he had no real need for school and even less need for after-school activities. What was the point? As far as he was concerned, he’d already mastered life.

“What about a guitar class?” I inquired.

“Naw. You already told me that I’m an amazing guitar player,” he reminded me.

“But…you don’t even play guitar.” I looked at him, confused.

“Air guitar, duh! It’s even harder than regular guitar because I can’t see the strings!” he rebutted.

As much as I wanted to argue, I loved Sid’s extreme confidence, his naiveté, his gusto! I also wanted to savor it because I knew it wouldn’t last forever.

When Sid started kindergarten this past fall, I noticed a shift. His self-awareness started expanding. He was exposed to more children, more ideas, and more challenges. Predictably, he began comparing himself with other kids and shying away from things outside his comfort zone. He was no longer the best at everything, and he knew it.

It feels like a punch in the gut when you learn that your kid wasn’t picked first for soccer or when you hear him berate himself for not knowing the right answer on a pop quiz. It’s heartbreaking not just because of our tendency to over-identify and remember all of our own struggles (I never made the tumbling team!) but also because as parents, we lose our ability to kiss all things and make them better.

Yet, we should want our kids to experience the sting of disappointment because it’s an invitation to overcome. It is how the good stuff happens. When I was in grade school, I was diagnosed with dyslexia and separated from my classmates during reading time. Years later, my high-school counselor told me that UCLA would be a long shot. I not only got into UCLA, I graduated a year early. My grammar may be terrible, but I’ve made a career out of writing and authored two best-selling books.

I was never a straight-A student, prom queen, or sports star. But I was always determined and scrappy and willing to make mistakes. I cried a lot because things weren’t easy. But then I managed to take each no as more of a dare than a don’t.

I didn’t set out trying to smooth the road for my kids; that just happened because of how much I love them. No one intends to be a snowplow parent, but our impulse to protect can override logic and even personal experience. I have to remind myself daily (sometimes hourly) to get out of the way! To let my sons fall down so they experience getting back up. Letting them avoid struggle is like robbing them of their own heroes’ journey. And if life were too easy, what would be the fun?

“Fine, I’ll try a guitar class,” Sid said after weeks of contemplation. “But what if I’m bad at it?”

“You are going to start out bad at it!” I told him. “That is why it is so exciting.”

Jenny Mollen has two sons, is married to the actor Jason Biggs, and has an avid Instagram following on @jennymollen.

This article originally appeared in Parents magazine's May 2020 issue as “The Challenging Gift of Failure.” Want more from the magazine? Sign up for a monthly print subscription here.

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