Looking Back: One Year of Fail Better

It’s finally here: the one-year anniversary of the launch of Fail Better. This moment brought out a lot of feelings and jokes about what it’s meant to make this show and have the conversations I’ve had, and you get to hear me talk about that here. Then I play one of my favorite interviews I’ve had, with the one and only Rosie O’Donnell, who enthusiastically joined me in challenging the standard format and purpose of a podcast episode. It was a special conversation with a special person, and one that I think represents this show pretty damn well. Cheers to a year, and to more conversations to come.

Rosie O'Donnell’s famous friends tell her she’s no good at being a celebrity. And if she’s honest, she’s never really felt like one. Despite her iconic roles and mass appeal, Rosie says she always identified more with the viewers at home rather than the stars she was interviewing on her long-running talk show. We got together in person to discuss all this, plus the devastating loss she suffered as a child, and what we both think about meeting fans at conventions. Rosie might feel iffy about fame, but that doesn’t mean the “it” factor that propelled her there isn’t still a driving force in her creative and personal life. And she’s continued to inspire others, too — just ask Eminem.

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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: 56
• Latest episode: 2025-05-13
• Society & Culture

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