News and Happenings

The author of In Praise of Failure, Costica Bradatan, joins me from Romania to share his wisdom on all things lack and loss. We talk about the true meaning of humility, the benefits of clumsiness, and just how broken democracy is — and has been — across time and place. Plus, we discuss quite possibly the biggest failure of all, the one none of us can avoid: death. I got to indulge my latent philosophical bent in this conversation, meaning I could even comfortably confess that I tried to work an 1880 parable into The X Files.

As the presidential administration turns over, it feels like an important time to revisit the family dynamics that brought about Donald Trump. His niece, Mary Trump, has long lived in the shadow of her family’s name. And as she writes in her memoir, Who Could Ever Love You, the darkness of that shadow affected generations of Trump children long before it took hold of the world. We talk about her grandfather, Fred Trump, the business-minded, manipulative patriarch who molded his son Donald in his own sociopathic image. It’s a vivid family portrait, explaining so much about the systems and ideologies that created a man so reluctant to fail.

Throughout his long and varied career, Rob Lowe has become an expert at reinventing himself. He left behind his bad-boy image from iconic 80s movies to work on a clever mix of dramatic and comedic TV roles. But I’ve known Rob for a while, and he’s a very layered individual. We look back at how Rob has pursued his passions and how he and his wife, Sheryl, have used practical techniques to keep their marriage strong for 34 years and counting. Plus, we discuss the difference between humility and humiliation, and why Rob is always down to be the butt of the joke.

I’m no self-help guru. And while I don’t think Gretchen Rubin would identify as one, she’s dedicated her work to figuring out just what the hell it means to live a full life. As a writer and former lawyer, Gretchen has spent years trying to understand happiness, the ways she can access it herself, and how to bring others in on the wisdom she’s gained. We talk action-led thoughts and aphorisms — anything in pursuit of leaving a conversation feeling happy (or at least, as Gretchen would say, happier).

As 2024 comes to a close, I’m feeling grateful for the conversations this show has allowed me to have, including the one that started it all. In honor of the growth (and growing pains) since the show launched earlier this year, I’m sharing the first episode of Fail Better, featuring the one and only Ben Stiller. It was my first-ever interview, and it unlocked something that I’ve continued to explore with every other generous guest who’s come on. I hope you enjoy.

The actor Alec Baldwin has spent a lot of time at life’s intersections. He came of age with challenging circumstances on one side and larger-than-life role models on the other. And when you look at how he works or how he parents (he’s now a father of eight), you’ll see that the duality has stuck around. He and I talk about how it’s possible to feel regret and gratitude in one breath, the specific things he’s learned from writing, and how much more we both hope to gain in the years ahead. It’s a personal conversation, and it feels necessary — though we both hesitate to use the word “therapeutic.” Let’s leave that to the experts.

As the United States Surgeon General, Dr. Vivek Murthy is dedicated to keeping the public healthy and safe. But these days, that involves much more than just cigarette warning labels. Dr. Murthy knows health should be looked at holistically, and he’s used his position to spotlight topics you might not think of as health crises, like gun violence, loneliness, and social media. We discuss his values, the harrowing confirmation process when he first became Surgeon General, and how he defines success and fulfillment, no matter what lies ahead.

Jack Halberstam, the author of The Queer Art of Failure, is someone I’ve wanted to talk to since I first started this podcast. As a professor and scholar, Jack has dedicated his career to dissecting the often-radical undertones of popular cultural media. Together, we look at how animated kids’ movies like Shrek, Finding Nemo, and Chicken Run offer critiques of a system that fails so many of us. We also talk about Jack’s experience as a queer child in England, since where we come from always informs where we go. It’s a wide-ranging conversation that calls into question the very essence of this podcast, as we examine what it means to be a failure in this world — and why Samuel Beckett’s phrase “fail better” isn’t all that inspiring when read in context.

It was a real magic moment to connect with Aimee Mann, a musician I’ve listened to for decades. She indulges my curiosities about lyric choices and instrumental training, and I learn how much goes on behind the scenes of an Aimee Mann production. We talk about the traumas of her past, which hardships do and do not influence her work, and why there feels like a creative imperative to turn pain into art. Then, to lighten things up (at least a little) we bond over some of our favorite artists of years past, like the sneakily somber Steely Dan.

Gillian Anderson and I share a connection unlike any other. The Dana Scully to my Fox Mulder, we are the only ones who understand what the other was going through during those X-Files years. But so much was left unsaid — until now. We got a chance to open up about the ways we might have failed one another during that wild ride, and we both examine the ways we’ve grown since. Gillian also caught me up on all her ventures and adventures — her work, her writing in the sexual fantasy compilation Want, and her cheeky new “unconventional wellness” line of soft drinks. It’s good to rediscover an old friend.