Why I’m Rooting for My Kids to Fail

This week the kids went back to school. Sienna is now a first grader and Asher is in Pre-K! When they talk about the days being long and the years being short, they must have been talking about parenthood! As we walked into school and posed for the obligatory first day of school photo (photos I cherish), I couldn’t help but reflect on how much my kids have grown over the summer, how much they have learned, and how much they have failed. And it’s the failures that I’m most proud of.

Early this summer, Asher was afraid of his new “big boy” mountain bike (no training wheels on this baby!). He climbed on top of that bad boy, his toes barely touching the ground, and promptly fell. That was it. He didn’t ride the rest of the day or for the next three days. Then I got on my bike to ride around, modeling and leading by example, in the hopes that he’d want to join in the fun and get back on his bike. It had to be his decision. After he saw me riding, he wanted in and so we took his bike in to the backyard where, if he fell (and we knew he would), he’d fall on the grass. And he did. A lot. But every time he fell I encouraged that failure. We spent countless hours in the backyard every day working on riding his bike and BOOM! He got it. Next he was riding on the road, and then BOOM! he was at the local mountain bike trail ripping through the woods. People can’t believe how good he is at riding a bike at only 4 years old. But I know why. It’s because of the constant failure.

I’m rooting for my kids to fail. It’s the fastest way to learn, to become more self-aware, to understand their limits and push further, it’s how they grow. A helicopter parent, I am not. We want our kids to grow up (safely) as independent, giving, confident, and curious individuals. As parents, it’s not our job to clear the path (i.e. make life easy) for our children. It is our duty to mentally prepare our kids to clear their own path.

If kids never fail then they never learn how to stretch their limits, to reach for their goals, to grow. Failures are the fastest way to spiritual growth. People actually ask me all the time how I am able to take on so much risk. The answer? Because I have made peace with failure a long time ago. I do not fear failure. If I fail, great. I’ll fix it, learn from it, and go out and build/grow/create again. I mean, what is the worst thing that could happen? I lose some money? You can always make more money. Make peace with failure and then nothing, I mean nothing, can hold you back from reaching your potential. If you don’t learn how to dance with fear, fear will hold you back daily. I know that is not the example you want to be for your friends, family, and especially your children. Yet it will be incredible hard, perhaps impossible, to encourage your kids to take risks, go after their dreams, go big or go home, if you are allowing fear of failure to hold you back.

I am very open with my kids about failure in my language and in my actions. I don’t hide my mistakes and I share with my kids when I’ve been wrong. The other day I knew the answer to some inconsequential question and Asher said, “Dad, you’re so smart.” I could have easily just said “thank you” and moved on. Instead, I corrected him and said, “Actually Asher, I know very little and strive every day to learn more.” I don’t know everything and don’t want my son to assume that I do. I want him to keep asking questions and to question me. We must model the behavior daily that we want our children to adopt. If we are fearful, hesitant, always playing it safe, what will that mean for our kids? Are we shielding them for learning and growing because we don’t want them to fail? Are we letting them skip a school concert because they didn’t practice the flute? Do we help them finish a project last minute because we don’t want to be that parent with that kid? Do we tell them not to go out for the football because we don’t want them to get cut from the team? Believe me, it says a lot more about you, then your children if you are always saving them from failure and the consequences that come with it. You’re also allowing them to miss out on all the incredible lessons that come from failure. There are many, many times in our life when we feel like we are helping our kids by clearing the path for them, but we are actually limiting their growth.

I want my kids to fail. It means they are trying new things and finding their way in the world. Our energy and efforts must be put into teaching them how to think for themselves, encouraging their ideas, and modeling the behavior we want them to exhibit. If we do this, our kids will be unstoppable. If we want to show our kids how to fail and that we are okay with it, we must talk the talk and walk the walk. We must:

  1. Tell our kids daily how we have failed. We must tell them that we don’t know everything. We must share our mistakes and what we have learned. Your future self, as well as the future version of your kids, will be shaped by the language you use with them.
  2. We must model the behavior of failure. Are you stepping outside of your comfort zone? Are you failing? How are you doing this? Words are powerful. Actions speak even louder.

How are you encouraging failure today?


  1. Michael Mergell

    We love to give our kids everything. Why not give them their failure so they can learn. That with our support and guidance from our own past failures will help them be stronger, independent people. Great Blog.

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  2. Michelle Canilao

    I feel blessed and encouraged every time there’s a new blog post. I just want to say, “Thank you.” There were many times during work when I would feel discouraged and felt like I hit many walls after weeks and weeks or tackling situations bigger than myself, but reading these blogs every morning to start my day give me the strength and perspective to, as Katrin Davidsdottir would say, “be the best me” I can be. I cannot thank you enough. You are a role model and while you’re on your own journey of learning and growing. I am as well! We got this!

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