I Never Had So Much Fun Losing: Leadership Lessons on Resilience

A dear friend of mine, Lorna Sherwinter, texted me last week and she pointed something out that I haven’t stopped thinking about. (Go read her Substack here focused on sharing micro-dosed solutions to disconnecting from your phone so you can reconnect with your life – as a busy working mom with two young kids, this lands!)

She highlighted the difference in Nick Baumgartner’s response across two Olympic cycles at the Winter Olympics.

Same athlete. Same stage. Same outcome: (Spoiler alert: he didn’t win either time.)

In 2022, after being eliminated from the individual snowboard cross event, he said, sobbing, “I’m 40 years old. I’m running out of chances. I have so much support back home, and I feel like I let them down. This one stings. This one hurts.”

I felt it with him! The weight. The pressure. The identity wrapped around the result.

Fast forward to this year. After narrowly missing advancing at 44, he said:

“I love this so much. And if you find something you love, it doesn’t matter how much work you got to put in. You’re happy to do it…I’ll continue to do it because I love what I do. I never had so much fun losing in my life! It’s a great time.”

HE HAD FUN LOSING!

He’s not delulu. He’s evolved!

And if you’re a high-achieving parent in a leadership role, I know you’ll get this because you are used to delivering. Used to performing. Used to being the one who pulls it off.

But in those times when you didn’t get the promotion? When the strategy didn’t land? When your kid was struggling and you couldn’t fix it?

How long did it sting? Could you still find steadiness?

Between those two Olympic moments, the outcome didn’t change.

HE did. And THAT’S the work.

It’s not pretending losing doesn’t hurt. Instead, it’s not collapsing your identity when it does.

Your kids are watching how you handle disappointment.
Your team is watching how you handle setbacks.

And you are teaching yourself who you are when you don’t get the medal.

How can you have more fun when you’re losing?

 

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