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.

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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.

Follow me on Instagram at @davidduchovny. Stay up to date with Lemonada on Twitter, Facebook and Instagram at @LemonadaMedia.

Joining Lemonada Premium is a great way to support our show and get bonus content. Subscribe today at bit.ly/lemonadapremium. And if you want to continue the conversation with other listeners, join the My Lemonada community at https://lemonadamedia.com/mylemonada/

For a list of current sponsors and discount codes for this and every other Lemonada show, go to lemonadamedia.com/sponsors.

See omnystudio.com/listener for privacy information.

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.

Follow me on Instagram at @davidduchovny. Stay up to date with Lemonada on Twitter, Facebook and Instagram at @LemonadaMedia.

Joining Lemonada Premium is a great way to support our show and get bonus content. Subscribe today at bit.ly/lemonadapremium. And if you want to continue the conversation with other listeners, join the My Lemonada community at https://lemonadamedia.com/mylemonada/

For a list of current sponsors and discount codes for this and every other Lemonada show, go to lemonadamedia.com/sponsors.

See omnystudio.com/listener for privacy information.