I’m Learning to Let My Kids Fail Now ⏤ So They’ll Be Successful Later

At the end of the day, my kids are only entitled to two things: a fair chance and the unconditional love of their parents.

by Jeremy Michael Wilson
Originally Published: 

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I’ve come to a conclusion regarding my kids: I have to love them enough to let them fail. Let me clarify. We all want the best for our kids. We want them to grow up happy, healthy, and most of all successful. We put a lot of emphasis on that last bit ⏤ successful. Why? Simple. We won’t be around forever, and we want to know that they’re going to be okay when we’re gone. Something that has been bothering me though, is that in trying so hard to make them succeed, we’ve set them up to truly fail.

We’ve made them afraid of failure. It’s as if we’ve come to the conclusion that if they don’t receive recognition or reward for everything they do, their tiny egos won’t be able to handle it. Why are more and more kids presenting with crippling cases of depression and anxiety? Because we don’t let them learn to deal with failure, frustration, and adversity. We don’t let them develop the tools to turn failure into success. We let them skip the work and go straight to the reward, never showing them how they’re supposed to get there.

Here’s a hard fact: not all of our kids are born superstars. As much as we would all love to believe we’ve given birth to mental and physical prodigies, it’s simply not the case. They’re not going to be perfect at everything. Odds of your kid just naturally becoming the top student or athlete in their class are slim to none. At the end of the day, my kids are only truly entitled to two things: a fair chance and the unconditional love of their parents. That’s where letting them fail, letting them lose comes in.

It’s our job to teach them that losing isn’t the end of the world and that wanting something doesn’t equal deserving it. They have to learn that just showing up isn’t enough if they want to win the trophy or the gold star. The only truly worthwhile participation award is experience. If they want the gold, they’re going to have to work for it.

I’m not going to do your homework for you. I’m not going to jump up and down and scream at your little league coach that you need more play time when there are other kids who are performing better for the team. If you want to make the starting line-up, it’s going to take time. It’s going to take practice. It’s going to hurt, and it’s going to take sacrifice. You have to make the decision if it’s worth it. I can’t make that decision for you. By the way, I still love you.

Letting them experience setback and disappointment doesn’t mean we don’t care. On the contrary, it presents the opportunity to show just how much we do love them. They don’t have to be stars for us to adore them. We already do. I worry that we’ve come to a point in history where we have so many luxuries, so many advances, that we’ve decided that one never needs to want or to experience setbacks. Here’s the problem ⏤ if they never want, what do they have to reach for? If we give our kids everything we want for them, if they develop the attitude that someone else owes them what they want ⏤ whether it’s parents, teachers, employers, or government ⏤ what happens when we’re gone and all those other establishments have decided otherwise?

This isn’t some profound or new perspective. It’s as old as teaching a man to fish so he can eat every day. We’ve just lost sight of it. We’ve put more emphasis on material success than personal success. There is a difference. Personal success to me is having the confidence to know that you can handle what comes at you, that if you get knocked down you’ll find a way to pick yourself back up. It means knowing you’ve earned what you’ve got, however much or little that may be, and knowing that no one can take it from you. It’s being okay that someone else may have a better car, nicer clothes. I’m okay with what I’ve got. However they may have gotten theirs, whether or not I think they deserve it, is immaterial. I can’t focus on how they got theirs. I have to focus on how I can get mine, in a way that doesn’t come at the expense of others.

It also means accepting your limitations. So maybe my kid isn’t going to be the greatest baseball player in history. Maybe he’s not going to be a Pulitzer prize-winning writer. I’m fine with that on two conditions: the kid has put as much effort as can be expected into whatever he’s doing; and he knows that while I won’t carry him up the mountain, I’ll be there to catch him when he falls.

Here’s the hook ⏤ we have dreams for our kids. Those dreams are not nearly as important as their own. They’re not here for us to live vicariously through, to achieve the dreams we didn’t achieve ourselves. If you want them to succeed, let them fail. Let them know failure isn’t the end. Rather, it’s the beginning that leads them to truly understanding what they are capable of. Let them know that even if their dreams aren’t the ones you’d have chosen, you’ll still support them. Let them fail so they learn to succeed.

An overgrown man-child and connoisseur of geek culture, Jeremy Wilson is striving to raise his two sons to become more responsible, self-actualized men than himself. So far they are not cooperating. You can read more of his writing at

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