Why You Should Fail

I've been a skier all my life. I picked up snowboarding because I quickly outgrew the mountains I skied on the East Coast. I got bored and figured I would give snowboarding a try.

After the first day, I want to say I fell 100 times. My ass was beet red. After the 2nd day, I had a bad headache from catching an edge and slamming face first into the snow/ice another 100 times.

The first barrier is deciding to try something. A lot of people are scared to take the first step. They are scared of failure, so they don't even attempt it. The second barrier is after slamming your face into the snow 100 times. The skill you wanted to acquire turns out to be tougher than you originally thought.

It was objectively embarrassing to face plant over and over on the mountain. I was the worst on the mountain, and everyone knew it. I don't like to be bad at things. I don't think anyone does. I also knew I could throw on skis and fly by all the people flying by me. I assumed they must all be mentally laughing at how bad I am.

I was certainly tempted to put the skis back on. I don't remember why I kept going, but I did.

On the third day, things clicked. I could actually board down a green. What gives me excitement is the feeling of going up a learning curve. I could feel myself getting better each run. It was an addicting feeling. My area of competence enabled me to complete a run without falling. I constantly pushed myself to go faster. The moment I fell was the moment I had pushed myself outside my area of competence. I got up the learning curve quickly because I kept testing my boundaries. Testing what I was capable of.

Falling in snowboarding or skiing is a great thing. It shows you are pushing yourself beyond what you're capable of. The next step after failure is to think about what just happened. Maybe I leaned on my backside too much. Maybe I dove from my left edge to my right edge too quickly. The way to improve is to reflect on what went wrong in the moment after failure.

Learning in the real world requires failure. It requires embarrassment. If you're not experiencing both, you're not testing the boundaries of what's possible. Most people are far too fearful of failure, and as a result, never grow. The inertia is to stay the same. If you want to become the best version of yourself, which why the fuck wouldn't you, then you need to fail.

On another trip snowboarding with my friends, I decided I would learn how to do a 180 by the end of the day. I went from a fairly competent boarder to looking like an absolute idiot, jumping and attempting a 180 every ten seconds down the mountain. I face-planted on average once every thirty seconds that day. At one point, some bystander who'd been watching me make a fool of myself skied down to my buddies and started chirping me, saying I thought I was Shaun White and needed to relax.

Funny enough, this was actually the worst thing I could conjure in my mind of what might happen if I fell a bunch while trying to land a 180. It was someone pointing at me, laughing, and saying "what an idiot!"

Once that happened, I became even more emboldened. The worst had happened, and I came out unscathed. I started trying a 180 every 5 seconds.

By the end of the day, I had mastered the skill.

Snowboarding is a tangible example of how all learning works.

To learn, you first need to take the risk. To take a risk, you need to test the boundaries of your area of competence. You won't expand your area of competence otherwise. In order to take that risk, you need confidence. Confidence to take the risk and to bounce back when you inevitably fail. That's why having "delusional optimism" is truly a great quality. Last, you need to gather accurate feedback when you fail, so you can learn how to improve.

Once you acquire the skill, you get to use that skill. Snowboarding is one of my favorite sports. I love the feeling of carving through snow as I fly down the mountain. I feel alive in a way that few other activities make me feel.

There are a couple lessons for me to take away from this article. The first is if I build up the energy to embark on a new skill, I must not quit. I must give it a minimum of 100 hours. If I still don't like it after 100 hours of trying, then okay. The second thing is to go fail. Everyone is psychologically averse to failing. From not approaching a woman at the bar to not signing up for that hard math class to not networking with people at the dream company that you want to work at. If you want it, the first step is to reach for it. Inevitably, you will fail some of the time. In that moment of failure, rather than letting it define you, learn from it and approach the challenge again with the same confidence and energy of life.

I wrote this article at a mid mountain stop in Park City, Utah. After, I found a park and started to learn how to ride rails and land the jumps. I was emboldened by this article to go fail. I lapped the park 10 times. I counted 20 falls, 1 bloody nose, and a bruised rib. But I also successfully entered and exited 5 rails, landed 3 180s off a box, and landed a jump where I grabbed my board horizontally. Every time I fell, I told myself "you have to be bad to be good."

Hopefully I've emboldened you to go fail.


Bonus clips of me ambitiously trying to land a 360 the day I learned a 180: