When Losing Becomes Winning: The Courage to Fail Spectacularly
How a devastating defeat at Wimbledon became a lesson in human resilience
This Week’s Courage Newsletter
"Pain can burn you up and destroy you, or burn you up and redeem you." - Marianne Williamson
Why spectacular failure might be your secret superpower
Scare Your Soul Challenge: The Failure Reframe
Bottom line: Sometimes the bravest act isn't winning - it's how courageously you lose
Dear Courageous Souls (and Secret Sportsball Fans),
Last weekend, my wonderful girlfriend Dana was off in Palm Springs for a girls' weekend.
Dana is not exactly what you would call a sports fan (she lovingly calling all sports "sportsball"), I found myself completely free to indulge in my guilty pleasures: sports documentaries and live sports on TV.
Little did I know I was about to witness one of the most courageous acts I've seen in years.
It didn't happen during play.
It happened after one of the most brutal losses in tennis history.
Amanda Anisimova, a 23-year-old American who had just pulled off an incredible upset against world #1 Aryna Sabalenka, had just lost the Wimbledon final 6-0, 6-0. In 57 minutes, she'd been completely dismantled on one of tennis's biggest stages.
Then came the moment that stopped me cold.
Fighting back tears during her post-match interview, Anisimova did something extraordinary.
Instead of deflecting or making excuses, she stood there - vulnerable, raw, and completely honest.
She thanked her opponent.
She apologized to the fans.
She broke down praising her mother, who had supported her through her father's sudden death and an eight-month sabbatical from tennis.
"I know I didn't have enough today, but I'm going to keep putting in the work," she said, tears streaming. "I always believe in myself so I hope to be back here again one day."
As noted by The New York Times, Harvard Business School professor Amy Edmondson calls this a masterclass in what she terms "intelligent failure." According to her research, the most successful people and organizations aren't those who never fail - they're the ones who fail better.
Here's what makes Anisimova's response so powerful
She owned it completely. No excuses, no blame. Just "I felt frozen there with my nerves."
She reframed it immediately. While still on that court, she chose growth over shame: "If anything, I can look at it as a positive."
She stayed generous. Even in devastating defeat, she celebrated others - her opponent, the fans, her mother.
She committed to the process. Not to winning, but to "putting in the work."
Edmondson identifies three types of failure: basic (simple errors), complex (system failures), and intelligent (failures in new territory while pursuing a goal). It's that third type - intelligent failure - that leads to breakthrough discoveries and growth.
Think about it: every scientist whose hypothesis proves wrong gets closer to truth. Every entrepreneur whose startup fails learns what doesn't work. Every athlete who loses spectacularly discovers their edges.
Pete Sampras once called losing to Stefan Edberg in 1992 the pivotal match of his career - because it taught him he hadn't truly wanted it enough. He won 13 more majors after that loss.
The difference? How we respond in those brutal moments when the world is watching and we've fallen short.
This Week's Scare Your Soul Challenge: The Failure Reframe
Warning: This challenge might make your palms sweat. That's how you know it matters.
Identify a recent failure - something that still stings, whether at work, in relationships, or a personal goal you missed.
Write a "post-match interview" - Spend 5 minutes writing as if you're being interviewed about this failure. Include:
What actually happened (own it fully)
What you learned
Who you're grateful for despite the outcome
How you'll move forward
Share it with someone - This is the scary part. Tell one trusted person about your failure using your reframed narrative. Notice how it feels to own your story with courage instead of shame.
Remember: We're not celebrating failure itself. We're celebrating the courage to transform our failures into fuel. To stand in our truth when every instinct screams to hide. To choose growth over protecting our ego.
Sometimes the most courageous thing isn't how we win - it's how spectacularly, honestly, and generously we're willing to lose.
With courage, compassion, and a new appreciation for "sportsball,"
Just had an incredible conversation with Mitch Matthews on his Dream Think Do podcast! We dove deep into harnessing everyday courage and breaking through what's holding you back. Mitch asks the questions that make you think - and might just change how you approach fear forever.
Coming This January, 2026: A Courage Immersion at Kripalu
Something special is brewing..! This January, I'll be co-leading an intimate courage workshop at the renowned Kripalu Center in the Berkshires. Imagine three days of transformative practices, breakthrough moments, and a supportive community - all in one of the most beautiful retreat settings in the country.
Interested in insider access and early information? Fill out this quick form and be the first to know when registration opens.