What rollerskating is teaching me about fear and failure

Yeesheen
3 min readFeb 23, 2021

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About a year into the pandemic, I decided to become an adult roller skater.

A rollerskater’s legs from the knees down — white roller skates, striped white and red socks, pink wheels.
Photo by Laura Stanley from Pexels

It’s a perfect pandemic hobby: nostalgic outdoor fun requiring only a pair of skates, knee-pads, an empty basketball court, and maybe a good playlist. It’s joyful; unburdened by expectation.

I quickly learned that I wasn’t alone in my enthusiasm. My Nextdoor post asking “where to skate” received a hundred excited recommendations. Each park I venture to across East Oakland, West Oakland, and Berkeley has its own loose clump of skaters of all ages and skill levels, wobbling through “bubbles” or gliding confidently into hockey stops on the smooth pavement. On Instagram, I peer at the park parties organized by DJs, food vendors, and skate-dance instructors, all sparkling with the forbidden allure of strangers gathering to have a good time.

For now, I’m still a beginner — which is a beautiful thing to be.

Yesterday, on a mostly empty court at sunset I rolled comfortably through my warmup exercises — and suddenly fell! I got up, adjusted my kneepads, and continued with practice. And then I stumbled again. I hit the pavement three more times in that 45 minute session, while looping through cross-overs, reversing direction, and once simply by losing my balance.

Each fall stopped me in my tracks and somehow, my joy in skating grew.

I realized: I’m not afraid to fall. I want this feeling all the time, in work and in life.

When I first started skating, I’d felt wobbly, loose, and out of control. My body would tense each time a foot shot forward unexpectedly. But when I actually fell for the first time, racing down an empty parking garage at a speed I couldn’t tame, the ice was broken. I knew I could fall — and it might hurt a little (thank goodness for protective gear) — but I’d just get up and do it again. I didn’t have to fear it.

I remember this feeling from practicing arm balances in yoga and learning to snowboard. You probably know it too from times when you worked to learn something new.

The knowledge that I can literally fall and get up again breaks open a whole new level of confidence. I can shed that fear and remove the finality from failure — to experiment more, find the edge, and learn faster with more fun.

One of my constant personal and professional goals is to take more risks. Like all perfectionists, I live with a fear of failure and its consequences. Many risks, financial, at work, and even in relationships, have outcomes that can’t be absorbed by $5 kneepads. (And I think there’s a whole analogy between those kneepads and privilege that I won’t explore here yet.) But when I think about risk in the real world, I tend to focus atomically — this presentation, this investment, this conversation — which is sort of like pinning myself to success in skating this cross-over, this transition on the court. Sometimes justified, but a bit myopic.

The lessons that I take from learning to fall:

  • Relax and place my attention on the longer curve of growth
  • Allow myself the joy of that experience
  • Create and maintain space for my team to fall safely and learn
  • Create space for users to play and fall safely in order to learn

I’d love to hear your thoughts on loving the fall and fear of failure too.

On the courts, backwards cross-overs are next. See you out there.

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Yeesheen

Currently: PM @ Honeycomb. Formerly: PM, Growth @ Optimizely. Aries 🔥. Word nerd. She/her/hers.