The Midlife Chrysalis

Author, speaker, and “Radiant Rebel” Karen Walrond joins Chip Conley for a warm, inspiring conversation on how to age with joy, live on your own terms, and keep your spark alive.

From growing up between Trinidad and the U.S., to leaving engineering and law for a creative life, Karen’s story is full of bold choices and unexpected turns. She shares cultural insights on aging, how to break free from the “success script,” and the se...

What happens when a Harvard scholar, devoted Mormon, and mother of a child with Down syndrome begins to hear psychic messages—and decides to tell the truth no matter the cost?

In this powerful conversation, Martha Beck shares how leaving her religion, embracing polyamory, and facing her deepest fears led her to a life of radical integrity, joy, and healing.

If you’ve ever felt stuck, out of alignment, or afraid to be fully yourself—t...

What happens when a self-made billionaire steps away from the company she built and faces the big question: What’s next?

In this inspiring episode, the founder of Spanx opens up about her journey from door-to-door sales to creating a global brand, the emotional challenges of selling her company, and how she’s redefining success, purpose, and identity in midlife. It’s a raw and uplifting conversation about reinvention, intuition,...

What if midlife isn’t a breakdown—but a breakthrough?

In this powerful conversation, world-renowned writer Pico Iyer shares the surprising lessons he’s learned from 50 years of friendship with the Dalai Lama, losing everything he owned, and finding stillness in the chaos. From walking away from success in New York to building a soulful life in Japan, Pico reveals how true freedom comes not from having more—but from letting go. This ...

What happens when a successful actor—and the son of a Hollywood legend—hits midlife and starts asking deeper questions?

In this powerful episode, Scott Eastwood opens up about building his own identity beyond Clint Eastwood’s shadow, what 40+ films have taught him, and why he’s now prioritizing purpose over fame. He reflects on masculinity, mentorship, mistakes, and what it really means to grow wiser with age.

What happens wh...

What happens when one of the most thoughtful voices in public life hits a wall?

In this deeply personal conversation, Krista Tippett opens up about burnout, walking away from success, and rediscovering joy in midlife. From letting go of exhaustion to falling in love again, she shares the hard-won wisdom that’s reshaping how she lives, works, and loves. It’s a moving reminder that it’s never too late to begin again, so don’t miss thi...

What if your so-called “midlife crisis” was actually a doorway to reinvention?

In this powerful conversation, Burning Man CEO Marian Goodell joins Chip Conley to explore how the radical spirit of Burning Man offers surprising lessons on aging, identity, leadership, and legacy. From embracing impermanence to finding purpose without a script, this episode is a deep dive into how midlife can be your most creative and meaningful ch...

What does it really take to start over at 69?

In this inspiring episode, Whole Foods founder John Mackey shares how psychedelics, purpose, and love reshaped his path after selling to Amazon.From ego death to building Love Life wellness centers, he opens up about business regrets, spiritual breakthroughs, and midlife transformation. You'll learn how conscious capitalism evolves with age—and why love might be the ultimate busi...

What if hitting rock bottom was the best thing that ever happened to you?

In this raw and inspiring conversation, Rich Roll, a former addict turned world-class endurance athlete, shares how he rebuilt his life from scratch, facing failure, financial ruin, and identity loss to find real purpose.

With brutal honesty, he opens up about his addiction, fatherhood, marriage, legacy, and the heavy cost of chasing approval. If you...

What if midlife isn’t a crisis, but your most creative chapter yet?

In this inspiring and deeply personal episode, bestselling author and entrepreneur Seth Godin shares how he’s reinvented his life through purpose-driven work, disciplined freedom, and the belief that life itself is a series of art projects.

We explore why the “dip” is a crucial part of growth, how to walk away from success when it no longer serves you, and wh...

At 40, Hoda Kotb’s world fell apart—cancer, divorce, and the dream of having children slipping away. But what came next wasn’t the end. It was a beginning.

In this amazing episode, Hoda opens up about surviving breast cancer, finding the courage to adopt at 52, and learning that her 50s would become the most meaningful years of her life. She shares raw moments, unexpected joy, and the wisdom that only comes from starting over.

What if the most powerful transformation of your life came after the titles, the heartbreak, and the noise? In this deeply moving episode, Maria Shriver opens up about rediscovering her identity beyond the Kennedy legacy, confronting the emptiness behind external success, and finally giving herself permission to become whole.

From her Catholic upbringing and complicated relationship with ambition, to the raw honesty of her poetry an...

What if midlife isn’t a crisis—but a chance to grow, heal, and start fresh? In this episode, Michael Franti shares how he transformed personal pain into purpose, why letting go of old stories changed his life, and how music helped him reconnect with himself and others.

Michael opens up about fatherhood, breaking free from emotional patterns, and the daily work of staying present in a distracted world. From his earliest songwriti...

What if the life you built is no longer the one that fulfills you? In this powerful episode, former venture capitalist turned CEO coach Jerry Colonna shares how his midlife crisis became a chrysalis—from collapsing under the weight of outward success to rebuilding a life rooted in meaning, connection, and emotional resilience.

He shares the moment he almost gave up, the books and mentors that helped him begin again, and why real lea...

Welcome to the very first episode of The Midlife Chrysalis!

Chip Conley kicks off this amazing podcast by redefining midlife. It’s not as a crisis, but a powerful chrysalis for transformation.

He shares his own wild journey and reveals why your 40s, 50s, and beyond can be the most meaningful years of your life. Plus, get a sneak peek at upcoming guests like Maria Shriver, Brian Chesky, Gavin Newsom, and more.

If you're ready to reinv...