Chris Evert Hates To Lose More Than She Loves To Win

After an illustrious tennis career, of course Chris Evert cherishes the wins and broken records. Yet, the sting of defeat is also etched in her memory, marked by days secluded in hotel rooms with the worst missteps replaying in her mind. Life as a high-profile athlete began for Chris as a teenager, and it opened her up to intense scrutiny from tabloids. But it also brought unprecedented levels of recognition and equality to the sport, introduced her to lifelong friends, and helped her grow in countless ways. Chris’s journey has continued to offer a mix of highs and lows, and as she speaks with me from retirement, she shares how she’s found even more ways to view the world around her, from her beloved sport to her ever-evolving spirituality. 

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To be human is to fail – period. And not just to fail once, but to fail a lot. As the author Samuel Beckett said: “Fail again. Fail better.” This saying means a lot to me and my family – so much so that my daughter got a tattoo of it. Why are we, and so many others, so deeply concerned by failure? And if it’s something we all do so often, why are we so afraid of it – especially those of us here in win-at-all-costs America? In this podcast, I sit down with successful, thoughtful people like Ben Stiller, Bette Midler, Sean Penn and more to talk about failure – or what they labeled “failure,” but what was really an unparalleled opportunity for growth and revelation. I even want to delve into my own hardest moments, when I wrestled with setbacks, shame, and fear. We’ll still fail again. And again. But maybe if we fail better, we’ll feel better -- and maybe if we can all laugh together in failure, that's a start.

• No. of episodes: 59
• Latest episode: 2025-06-03
• Society & Culture

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