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
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, 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.
Mar 13, 2026 • 56min
Why You Keep Repeating the Same Conflict Patterns | Diana Chapman
Diana Chapman, leadership coach and co-author of The 15 Commitments of Conscious Leadership, who coaches founders and CEOs on trust and reducing reactivity. She explains the Drama Triangle and playful tools to shift conflict. She discusses sustaining long relationships with curiosity and play, the zone of genius versus excellence, and the value of fallow ground and quiet for midlife transformation.
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.
