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
Apr 6, 2026 • 56min
Leading in Chaos: How to Stay Grounded Under Pressure | Amy Elizabeth Fox
Amy Elizabeth Fox, co-founder and CEO of Mobius Executive Leadership and author, blends leadership strategy with deep healing. She discusses why pressure can spark growth. Short takes cover vertical development, how past wounds shape leaders, midlife loneliness despite success, feminine soul leadership, and leading amid constant chaos.
Apr 3, 2026 • 1h 1min
She Told 80,000 Employees the Truth She Hid Her Entire Life | Katherine Dudtschak
Katherine (Katie) Dudtschak, a former senior Canadian banking executive who affirmed her gender at 50 and now writes and leads on storytelling and transformation. She recounts living a picture-perfect life while feeling incomplete. She describes the midlife awakening, the choice to come out publicly to protect her family and sanity, and her shift into leadership and storytelling for human change.
Apr 1, 2026 • 19min
Why So Many Men Lose Friends in Midlife (And How to Fix It)
They explore why social ties are the top predictor of a longer life. Conversation dives into why men often lose deep connections and the cultural and emotional reasons behind it. They contrast transactional relationships with real friendship and offer a simple habit to rekindle old bonds. The discussion also covers vulnerability barriers, post-career loneliness, and daily practices to rebuild community.
11 snips
Mar 30, 2026 • 53min
Death, Belonging, and What It Means to Be Human | Sebastian Junger
Sebastian Junger, bestselling journalist and author who reported on war and wrote Tribe, recounts a sudden near-death collapse and the vision that followed. He explores mortality, what near-death experiences suggest about consciousness, and why modern life erodes belonging. Short, vivid conversations about tribe, ritual, and how facing death reshapes how we live.
Mar 27, 2026 • 55min
How an Anarchist Built One of America’s Most Unique Businesses | Ari Weinzweig
Ari Weinzweig, co-founder of Zingerman's and author who blends anarchist ideas with business, discusses trust, dignity, and nonhierarchical leadership. He recounts Zingerman’s start, explains anarchism applied to organizations, and outlines dignity-driven practices and ZingTrain’s role. Short, provocative, and focused on rethinking how workplaces motivate and organize people.
Mar 25, 2026 • 26min
Men vs Women in Midlife: The Struggles No One Warns You About
A candid look at midlife struggles for men and women, from hormonal shifts to loneliness and loss of purpose. Conversations cover menopause, andropause, invisibility in dating and work, and financial and caregiving pressures. Practical themes include medical misinformation, changing identity, and the need for clearer communication and self-advocacy.
Mar 23, 2026 • 48min
Why Love Requires Skills Most People Never Learn | Terry Real
Terry Real, renowned couples therapist and creator of Relational Life Therapy, offers a concise mini bio and practical perspective. He explores why love needs skills people never learn. Short, punchy takes cover childhood patterns, how masculinity blocks intimacy, reclaiming connection in midlife, and concrete relational practices to rebuild closeness.
Mar 20, 2026 • 1h 2min
Pete Holmes on Psychedelics, God & Finding Meaning in Midlife
Pete Holmes, comedian and spiritual seeker known for blending humor with consciousness work. He talks about heartbreak that redirected his life, how comedy heals, the role of psychedelics in revealing awareness, and why midlife and parenthood bring steady contentment. Short, funny, and reflective takes on humility, truth-telling, and not believing every thought.
8 snips
Mar 18, 2026 • 26min
Midlife Pit Stop: Refuel Before the Next Chapter
They explore the rise of midlife gap years and why people over 50 are choosing resets instead of rushing to retirement. The midlife atrium metaphor reframes life architecture and intentional breaks. Practical ideas include starting with gap weekends, designing a one-month sabbatical, and how workplace sabbaticals can aid retention.
12 snips
Mar 16, 2026 • 57min
Designing the Second Half of Life: Meaning, Curiosity, and Becoming | Bill Burnett & Dave Evans
Bill Burnett, design educator from Stanford, and Dave Evans, former UC Berkeley instructor and co-author, bring design thinking to midlife reinvention. They discuss prototyping small experiments, reframing stuckness, curiosity over certainty, and treating midlife as a chrysalis for becoming. Short, practical ideas about testing new selves, embracing beginner’s courage, and finding meaning in everyday moments.
