When is the last time you set out to fail? Fell flat on your face, looked like a fool, tried something risky and FAILED? Have you ever, even once, started something with the sole intention of failing?
My guess? No. We’re programmed from birth to succeed. From the cheer of our mothers as we take our first steps, to the straight “A’s” we strive for in school, all the way through our multi-faceted adult lives, we are smiling, studying, and sweating our way towards achievement. Yes, we sometimes fail. But it’s generally not purposeful. We’re so used to the idea of a grading scale that we internally score ourselves on such disparate things as work presentations and parenting skills. And the grade is usually dependent on the same criteria: how do others view our performance? Is my child screaming? Am I poised for a promotion? Are my parents proud of me? What do my neighbors think after that loud fight I had with my husband about his dirty socks? An “F” is something we fight like hell to avoid and try our hardest to forget. We are programmed to avoid failure at all costs and instead seek achievement like a drug. The usual result? Mediocrity. A very commendable “C.”
If you want to master your fear of failure, learn to snowboard. When my then boyfriend (now husband), and I moved to a small Canadian town five years ago, we took up snowboarding to pass the time and make the best of the massive snowfalls we faced during the winter months. In the beginning, I thought that I would absolutely, positively never get the hang of it. First of all, I had to figure out how to ride a T-Bar to the top of the mountain, which translated to sticking a small bar behind my thigh with one foot unstrapped while holding onto a tow line for fifteen unbearable minutes. I fell. Many times. In the beginning, I took out my friends, a small child, and a metal sign that read “No zig-zagging.” I would fall off and have to walk back down the mountain in humiliation. Once, I fell near the top and had to walk up until I was so out of breath, I just wanted to throw my board down and go home. I hit my head, I fell on my butt, I got whiplash, I careened into deep snow piles, I rolled head over feet. I did all of these things more times than I can count. And then, one day, I was able to do it. I was a snowboarder.

This is me, during my second season of snowboarding. It captures that perfect moment right before the fall. Will, I won't I? Oh yes, I'm going down.

It may sound like that’s where the story ends. Fall. Get up. Repeat. But my real encounter with failure came later. We moved to Vancouver three years ago and said a fond farewell to T-Bars and a grateful hello to fast lift chairs and unbeatable terrain. I finally had the hang of snowboarding. Sometimes we would snowboard with people above my level, and sometimes with people below. And boy, did I love it when I could cruise at a moderate pace ahead of someone. That felt like achievement. And hadn’t I worked hard to earn it? I sure had. So I kept on cruising. Until I started to notice something. My chest would clench up with fear whenever the path was too straight and flat, whenever there were too many trees, too much ice, too many moguls. I would stop turning my board. I would slow down. I would sabotage myself.
I worked hard the first couple of years because I was fighting failure. I wanted to succeed at snowboarding, I wanted to stay up on the T-Bar, to stop hitting my head. Now I was playing it safe because I had no reason to fail. I could easily make it down most runs. Why should I risk hurting myself when I was an adequate snowboarder? But the safer I played it, the more I would feel that clench. You have to fail said a tiny voice. You have to fail so that you’ll stop being afraid of failure. I was using everything I’d worked so hard to achieve to keep myself perfectly safe and upright. I didn’t have to fall anymore so I tried my damnedest not to. My constant evaluation was one of risk and reward. There’s no tangible reward in careening off a jump and falling (literally) face first into the snow. It’s uncomfortable, painful even. So is sliding on a rail and falling on your butt or tumbling head first over an icy mogul. But that’s what I’ve been doing lately. Not really because I expect to master these things. I may never be able to do cool tricks or glide through tightly packed trees like a pro. That’s not the point. The more falls I learn to take, the stronger I become. The fear is dissipating because I’m no longer letting it control me; the clenching has eased. Failure has a fantastic side effect of making you less afraid.

Whistler Mountain. This view inspires me to fail harder.

I don’t have to tell you that this translates to all aspects of life.  We achieve a comfortable position at work where we feel capable and are unlikely to be fired. So we stay right there. We convince ourselves that we already have enough on our plates, so we don’t take up salsa dancing or learn the violin. We date someone who matches all of the practical criteria we laid out for ourselves early in life. Not wanting to fail at another relationship, we continue on.
I urge you to try failing at something small this week, something inconsequential. Just to see what it feels like. Is it freeing, easy as pie, or more difficult than you imagined? We can all do with a bit more intentional failure in our lives. I certainly can. The next time I head up that mountain, I’ll be repeating this little mantra in my head: “Fail. Then fail harder.”