Finding a Path to Failure

What my kids and I are teaching each other about taking risks

My son is seven years old, and he’s learning to play hockey. The first step in his journey is mastering how to ice skate. Every week, we go to the local ice rink, where I suit him up in so much gear that I wonder if there is more gear than boy—a helmet, face cage, padded hockey pants, knee and shin guards, elbow and forearm guards, and a chest guard with padded shoulders. It takes 15 minutes to put all this on, and it’s a 60-minute lesson.

Out on the rink, he and his teammates follow their coach to learn how to control their moves on the ice so that skating will be second nature to them as they start handling their sticks and pucks. The first time my son put a foot onto the ice, he fell headfirst. I could tell he was shocked, but he shook it off. He managed to get up, only to fall right back down onto his right shoulder.

Seeing that took me back to my own days learning balance sports, which I never mastered out of fear of falling or getting hurt. That same fear dominated everything I did as I grew older. I avoided things like learning to ski or ride a bike well because the first few experiences felt so shaky I was sure I’d injure myself before I could master the balance. Instead, I spent my time excelling at things I felt left little to no risk of physical injury, like practicing the piano and cello, writing, and reading—which all have a near guarantee of success the more you practice.

I envy those with the confidence to throw caution to the wind and take huge chances. That’s right — I am jealous of those who fail.

As I got older, this tendency followed me, and limited me, in every aspect of my life. I stuck close to the set of friends I had and didn’t force myself to make new ones unless I had to. I picked my college major and career based on what I thought offered the most steady employment opportunity. Despite intense interest and passion, I mentally pushed away visions I had of becoming a marine biologist (I could get mauled by a shark and die in the ocean!), anthropologist (What career would that lend itself to?), or journalist (How would I earn enough to eat?). Since my first formal job, I’ve dreamed of entrepreneurship, but giving up a steady income to try something that may not work out has felt too risky. I have led teams, managed large projects and profits and losses, and pushed new product launches. Not all those things worked out, but I always made sure I would land on my feet when taking them on—whether it was having a new solid job in the wings or knowing that I had relationships uninjured by any fallout.

Even now, I envy those with the confidence to throw caution to the wind and take huge chances. I am jealous of those who fail. It’s not exactly that they failed but that they overcame a fear in order to have a chance at more significant success. Not just learning to fail but embracing that failing is valuable cred, both socially and professionally. It’s what takes you to the next level of everything, even if there is a good chance it could take you nowhere or also hurt you.

I grew up in an immigrant home. My parents had taken perhaps the most significant risk there was in leaving everything they knew to start a new life in an unknown land. Likely for that reason, failure avoidance was ingrained into me the same as brushing my teeth twice a day. When you’ve risked so much to give yourself and your children a better life, the last thing you want your children to do is endanger that opportunity in any way. This nurture element combined with my general disdain for risk gave me the ability to identify and pursue the opportunities where my chance for success was high and the risk of failure was low. If something looks like it will fail, I’d abandon it immediately and move on to something with better odds.

It’s easy for someone on the outside to think this self-protective, risk-evaluating strategy has worked for me, and they’d be right. I am happy and have a wonderful life. I have the things I want, and I live comfortably. But it’s also easy to see the things I never even tried for fear of failing by taking a look at my bucket list: biking through a vineyard, living in another country with my family, scuba diving, having my own business. I’ve said no to job opportunities based on my desire for precise results in something familiar versus new, exciting things that may not work out.

How does someone like me teach their children to love risk?

I want my children to have bucket lists too, but the items on those lists should be there because they haven’t gotten to them yet, not because the fear of failure is holding them back.

It’s all made me wonder: How does someone like me teach their children to love risk? I’ve gathered a few ideas from watching my son’s journey to learn to skate:

Help Them Get Past the Fall

The first time my son fell learning to ride a scooter and again when he started learning to skate, I encouraged him to get back up and keep going. Once they’ve fallen, they know what it is and realize it’s not so bad.

Pad Them Up for Their Next Fall

They will fall again. It’s the only way to learn something new, so pad them up and encourage them to do things slowly and remember that when they fell before, they were okay.

Encourage Them to Try More

If they’ve already achieved something, like knowing how to do a forward swizzle, there is little point in continuing to make that same move over and over (except maybe for fun). Encourage them to try something new, and if they fail, so what? They still know how to forward swizzle.

This is the one rule that I think could have the most impact on encouraging someone to pursue their dreams. Take me for example: The fear of leaving a good-paying job to try something new, like starting a business or joining a startup, is inherently risky, but the “bottom” for me is that good-paying job. Have faith that if you want to go back to it (or something like it), you can. People do just that every day, and some of them go back to something better because they learned so much in their fall.

Break It Up Into Smaller Risks

Skating is one thing, but jumping on the ice can be scary. It’s something my son is still working on, but he tries in tiny ways every time. He will lift one foot and then the other, keeping both off the ice for a split second while he switches.

For me, I want to start a business of my own, but that sort of financial risk is not something I can handle right now. Instead, I’m working on a dinosaur drawings business with my son. I get to work on a company that he and I own, and he gets to learn the ins and outs of what happens if we can’t find a buyer for one of his drawings.

Teach Them to Be as Proud of Failure as They Are Success

I remember the shame I felt when I failed at something I thought I could do, but each failure teaches so much and makes you an interesting person. Embrace it. When he was learning to snowboard, my son told me he spent more time on his butt than on the board. But two lessons later, he was nearly ready for the chairlift and joked about how he knows how to fall the right way.

I’m not saying we should encourage reckless risk-taking in our children, like crossing a busy street with your eyes closed. But I want to give my children the gift of failure, the chance to see they can recover from falls, learn something new, and just maybe have a chance at outrageous success—that can only come from being open to failure.

Founder - | Dog Lover | UX Researcher | Mom of Two

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