the Practical Skateboarder

If failure is an essential part of getting better, then how do you do it well? How do you get better at failing?

When I was a younger skateboarder, I believed in the mantra, “Go big or go home.” I thought if something wasn’t all or nothing on any attempt, then it wasn’t worth doing. Sometimes though, this meant broken bones and weeks or months off my board to recover from serious injuries.

An older, hopefully wiser skateboarder now, I realize how foolish and reckless such a sentiment can be. Of course we want to do big things, but we cannot get there by going right after it. Otherwise, we break.

Choosing the right size of risk to take is just as important as taking the risk in the first place while getting better. No risk, no reward. But, too much risk and the downside could be irreversible.

You must learn to size the risk.

There’s no way to objectively prescribe for anyone how much risk is too much. At least acknowledging that failure is inevitable and that what you’re doing has risk provides you with enough perspective to choose wisely the risks worth taking.

The aim is to fail and get back up to try again. If the failure breaks you, then you cannot learn from it.

Some practical advice on how to develop an intuition for risk:

1. Start small and go to the edge of your comfort zone but no further. Eventually, your comfort zone will grow and so will your ability.
2. Commit to one attempt to see how it feels. Sometimes you have to make the leap from the flatbar to the handrail. There is no middle ground. Give it a real attempt and then check your gut. Is this the edge of your comfort zone or too far out?
3. Choose a series of obstacles to progress through. Start on flatground, then go to the curb, the 2-stair, 5-stair, etc. Each level builds confidence and capability. You’ll also start to notice where the edge of you comfort zone is and what it feels like in your gut when you’re there.