a woman sitting on the wing of an airplane

#104: A Lesson from Outdoor Adventures

Bob Ewing
January 20, 2023
a woman sitting on the wing of an airplane

Talking Big Ideas.

“Try again. Fail again. Fail better.” 
~ Samuel Beckett

I had an epic wipeout on Wednesday. 

Maryrose and I were skiing at our local resort with our friend Caroline. Conditions were perfect: sunny with lots of powder. We were having a blast and decided to up our game with the terrain park. We launched into the air several times when we came to the biggest jump on the mountain. 

Maryrose and Caroline crushed it. I couldn’t stick the landing. My skis and poles went flying in all directions as I somersaulted down the hill. 

I quickly realized I was unhurt – and felt more alive than ever. We rode the lift right back up and hit the terrain park again. I learned from my mistake and we all made it through without falling. That evening Maryrose asked what my favorite part of the day was. We had an amazing time, and I had to admit my favorite part was the wipeout. 

I’m taking group ski lessons now and our instructor reminds us that safely falling gives us useful feedback to help us grow. One of the students added that falling also shows we are pushing ourselves into the stretch zone, which is ideal for skill development. We talked about a rock climbing maxim: 

If you’re not falling, you’re not climbing hard enough.  

Climbers may spend months practicing one particular route. They’ll fall countless times. They’ll try a thousand different variations. This is especially true at the highest levels. 

Watch a few seconds of this clip showing Adam Ondra, one of the best rock climbers of all time, working a difficult route: 

Ondra knows he must fall a bunch before he succeeds. He says every attempt feels a little bit different. He learns something new with every fall, every failure. There’s no ego or embarrassment. Only maximum effort and slow but inevitable progress

The legendary pilot Amelia Earhart explains in her autobiography, The Fun of It, that she made it a habit to practice failure. She writes: 

Unless a pilot has actually recovered from a stall, has actually put his plane into a spin and brought it out, he cannot know accurately what those acts entail . . . The pilot who hasn’t stalled a plane is less likely to be able to judge correctly the time and space necessary for recovery than one who has.

Earhart wanted to experience all the possible ways things could go wrong so she’d be better prepared in the air. As Farnum Street says, “If we don’t practice failing, we can only safely fly on sunny days.”

Embracing failure can be hard. Especially at the office. 

Most executives and business leaders think failure is bad. This creates a culture where people avoid any type of failure at work. And when it comes to public speaking, there is the added anxiety of worrying that people will watch us embarrass ourselves.

I love it when clients finally open up and become confident enough to fail during our practice sessions. To push outside their comfort zones and try new and even absurd exercises.   

For example, if you’re bound to your notes, practice giving your entire talk without them. Every time you forget your spot, just forge ahead anyway. 

If you speak too fast, practice pausing longer than Steve Jobs introducing a new product. Practice speaking at half speed. Then quarter speed. Go painfully slow. 

If you speak softly, try practicing so you sound even louder than Steve Ballmer giving a Microsoft pep talk. 

Accept the awkwardness and keep pushing until you fail. And then repeat.  

Every time we fail we learn. And every time we fail we grow. The next time you have to give a big speech or do something that will be hard, I encourage you to be like Amelia Earhart and Adam Ondra. To paraphrase a climbing maxim:  

If you’re not failing, you’re not practicing hard enough.


Make it a habit to practice failure. 

Ask yourself, what is one way you can practice failure this weekend? 


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