The Midlife Chrysalis
Chip Conley
The Midlife Chrysalis is a one-hour podcast hosted by Chip Conley, bestselling author of Learning to Love Midlife and founder of MEA (Modern Elder Academy). Chip and his high-profile guests – including Maria Shriver, Hoda Kotb, Elizabeth Gilbert, Michael Franti, and more – dive into raw, vulnerable conversations about the profound transitions they’ve experienced in midlife.
Listeners get a rare look at how even the most successful individuals have to navigate life’s pivotal changes – and gain practical wisdom they can apply in their own lives for a more fulfilling and purposeful next chapter.
Listeners get a rare look at how even the most successful individuals have to navigate life’s pivotal changes – and gain practical wisdom they can apply in their own lives for a more fulfilling and purposeful next chapter.
Episodes
Mentioned books
9 snips
Mar 11, 2026 • 24min
From Ego to Soul: Rewriting the Second Half of Life
A conversation about moving from achievement-driven identity to a soul-led life. They explore why ego builds the first half of life but can limit the second. Topics include shifting from performer to elder, the ballroom dance metaphor for inner change, generativity and mentoring, spirituality and awe, and practical steps to soften the ego.
Mar 9, 2026 • 55min
Mortality Was My Wake-Up Call | Dr. Brad Jacobs
Dr. Brad Jacobs, a physician and longevity expert who founded Blue Wave Medicine and taught at UCSF, shares what reshaped his life after personal loss. He discusses sleep and wearables, psychedelics and ketamine for emotional healing, integrative health basics, rethinking U.S. healthcare priorities, and a new, balanced model of modern masculinity.
7 snips
Mar 6, 2026 • 1h 3min
Why Midlife Feels Like Exile And Why That’s a Gift | David Whyte
David Whyte, poet and philosopher known for work on poetry and midlife transformation, reflects on feeling exiled from your former life. He links Dante’s “dark wood” to moments of loss and possibility. He discusses silence, the unknown, poetry’s role in midlife, vulnerability, grief, and how friendship and work can become sites of inner pilgrimage.
Mar 4, 2026 • 22min
Letting Go in Midlife: What Has Run Its Course?
Chip Conley, bestselling author and founder of the Modern Elder Academy, brings concise midlife wisdom from a near-death experience and the sale of his company. He explores the Great Midlife Edit and the idea of emptying your cup. Short, practical frameworks appear: transitional stages, a gut-check practice, and ways to ritualize letting go. A clear invitation to release what has run its course and make space for what’s next.
Mar 2, 2026 • 51min
Greg Louganis: Olympic Gold, Public Masks, Private Truth
Greg Louganis, Olympic champion diver turned mindfulness and breathwork teacher who has spoken publicly about living with HIV. He recounts the life behind the medals, early wounds that shaped his drive, and why love mattered more than trophies. He discusses meditation, shadow work, psychedelics, and facing mortality while reinventing his identity in midlife.
12 snips
Feb 27, 2026 • 1h 2min
Midlife and the Moral Pressure of Limited Time | Kieran Setiya
Kieran Setiya, MIT philosophy professor and author who wrote a guide to midlife, reflects on regret, time, ambition, and meaning. He contrasts goal-chasing with ongoing, process-focused living. He discusses telic vs atelic activities, attention and attachment, and how anticipated regret can spur wiser choices. The conversation reframes midlife discomfort as a source of clarity rather than crisis.
Feb 25, 2026 • 28min
What a Cancer Diagnosis Teaches You About How to Live
A candid conversation about how a cancer diagnosis reshapes time, purpose, and urgency in midlife. They explore living with scans and uncertainty, the effects of hormone therapy, and reframing legacy as ripples rather than monuments. Practical ways to talk about mortality and the idea of memento mori surface as tools for choosing what truly matters.
8 snips
Feb 22, 2026 • 1h 8min
From Ambition to “I’m Enough” | Brian Chesky
Brian Chesky, co-founder and CEO of Airbnb and a designer-turned-entrepreneur, reflects on leadership, loneliness, and redefining success in midlife. He discusses imposter feelings, the IPO wake-up call, evolving from control to connection, rituals to rebuild friendships, and the Hoffman process that led him to the realization of being enough.
10 snips
Feb 20, 2026 • 51min
Your Brain on Art: Why Midlife Needs Creativity More Than Ever | Susan Magsamen & Ivy Ross
Susan Magsamen, a neuroscientist who studies neuroaesthetics, and Ivy Ross, Google’s design chief and longtime artist, explore why creativity matters in midlife. They discuss how art, play, and sensory practice support brain health, ways to rebuild curiosity and hands-on making, and the role of aesthetic thinking in leadership, tech, and personal reinvention.
8 snips
Feb 18, 2026 • 20min
Why Midlife Friendships Stop Working & How to Fix Them
A warm conversation about why midlife friendships can go quiet and how to rekindle them. They explore friendship as a learnable practice and talk about reconnecting with old pals. The discussion highlights moving from surface talk to vulnerability, practical ways to invite deeper conversations, and tips for gently shifting friend groups toward more authentic connection.
