News and Happenings

Stephen Dubner, host of Freakonomics Radio, has done more than change the way we think about economics — I consider him a spiritual guide of our time. But for all his success, he’s got a laundry list of careers he’s left behind, from rising-star musician to New York Times writer. We debate the merits of expecting the worst versus hoping for the best and discuss how to trade nuance for novelty as we get older. It’s never too late to keep learning — or, according to him, to start a podcast.

On stage and off, Sarah Silverman is always evolving, whether that’s honing her standup routines or coming to grips with missteps in her past material. We reminisce about our mutual friend Garry Shandling, including the comedy star-studded basketball games he used to host, where I first met Sarah. I also have the pleasure of talking to Sarah about the satisfaction of apologies and the struggle of forgiveness, and I realize, once again, that I extend much more grace to others than I do to myself. Lucky for me, Sarah won’t stand for that.

Like all of us, athletes fail often. Renowned tennis coach Brad Gilbert knows that well, and has spent decades analyzing weaknesses as a way to develop strengths. As a player, he rose to the rank of #4 in the world, then began coaching stars like Andy Roddick, Andy Murray, and, most recently, Coco Gauff. He even trained Zendaya for the movie Challengers. I loved hearing how the man Andre Agassi called “the greatest coach of all time” gets even more out of the best players in the game.

This is my most personal episode so far, but it’s really about the wisdom of Dr. Gabor Maté. The author, physician, and public speaker reminds us all how we sometimes become too comfortable with self-criticism and regret. We talk about parenting, collaboration, and addiction, and I leave the interview feeling a level of gratitude that I don’t know what to do with. Here’s that conversation.

You can get even more Fail Better with Lemonada Premium, where I share the extended thoughts I have after each interview. Here’s a free peek at what you could be getting: After my conversation with Bette Midler, there are many things I’m still wondering about because I couldn’t find a way to bring them up, including what I wished I’d asked her about parenting. Subscribe to Lemonada Premium now in Apple Podcasts.

Never in my life did I think I’d get to talk to Bette Midler, only admire her from afar. And while I can’t say the decorated performer is just like us, what I can say is that Bette was more than happy to sit down and talk to me about things that have gone wrong in her life. Tune in to hear about workplace horrors, how being self-deprecating doesn’t make me special, and what it really means to know thyself. All hail The Divine Miss M.

Believe it or not, Ben Stiller has failed. (Remember Zoolander 2? He’d probably rather you didn’t.) As it turns out, Ben has had his share of flops — a man after my own heart — and we chat for a good while about those times in his life, including how they sometimes led to something better. In my first-ever interview, he keeps me on track, answers questions I forgot to ask, and overall makes me feel like I’m actually succeeding at being a podcast host.