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
May 13, 2026 • 30min
What Keeps You Together When Everything Falls Apart?
A raw conversation about facing cancer recurrence, grieving a parent, and navigating sudden relationship and caretaking shifts. They explore purpose, community, and why staying open during unbearable change matters. Emotional honesty, transitional frameworks, and longevity factors come up as anchors when life unravels.
4 snips
May 11, 2026 • 54min
Feeling Stuck at 50: How to Find Your Magic and Start Again | Matt Ross
Matt Ross, entrepreneur and author of Grow or Fold who built School of Rock and founded One River School, shares his midlife reinvention journey. He recounts leaving radio, the crisis that sparked starting One River at 50, treating life like a business, and how to pivot, find your magic, and plan the next decade.
May 8, 2026 • 51min
What Horses, Death, and Nature Taught Me About Being Human | Kelly Wendorf
Kelly Wendorf, equine-assisted learning expert and author, blends horse wisdom with nature-based rewilding. She reflects on caring for a dying parent, how facing death reshapes life, and why nature quiets the nervous system. Short, vivid stories about horses and reclaiming your undomesticated self bring these themes to life.
11 snips
May 6, 2026 • 17min
AI vs Humans: The One Skill AI Still Can’t Replace
They explore which kinds of work AI will replace first and who is most vulnerable. They contrast knowledge with cross-domain wisdom and why judgment grows valuable. They discuss how AI can free mental bandwidth and practical first steps to start using tools. They warn against losing on-the-job learning and recommend curiosity, hands-on practice, and new interfaces like voice tools.
11 snips
May 4, 2026 • 55min
The New Way Women Over 50 Are Choosing to Live | Elizabeth White
Elizabeth White, author and advocate for women over 50, shares her journey from recession loss to reimagining midlife housing. She discusses why housing is the real pressure point, the rise of Golden Girls style co-living, how to know if shared living suits you, and the emerging “wisdom worker” era that reframes aging as an advantage.
25 snips
May 1, 2026 • 48min
You Were Never Meant to Think This Way | Angus Fletcher
Angus Fletcher, a professor, author, and advisor to U.S. Army Special Operations known for work on narrative and primal intelligence. He explores primal intelligence and the four core human abilities we lose with age. He explains why AI cannot replicate human thinking. He describes simple practices to rebuild intuition, creativity, wonder, and how reframing your life story can transform midlife.
6 snips
Apr 29, 2026 • 25min
Why Success Stops Making You Happy After 40
They dig into why high achievers often feel unfulfilled after 40. The conversation covers the shift from achievement to significance and three key questions that reveal deeper direction. They critique modern success ideals and compare cultural differences in happiness. Practical steps for reevaluating life areas and where people find lasting meaning are highlighted.
22 snips
Apr 27, 2026 • 47min
You Did Everything Right… So Why Does It Feel Wrong? | Jill Nykoliation
Jill Nykoliation, former CEO turned executive coach and MEA faculty, left a high-powered branding career to explore identity and reinvention. She discusses walking away from titles, how pandemic huddles revealed hearted leadership, using curiosity and testing to redesign life, and why stuckness can signal growth. Short, warm, and transformative conversation.
16 snips
Apr 24, 2026 • 57min
The Real Reason You’re Aging Faster Than You Should | Dr. Florence Comite
Dr. Florence Comite, a Yale-trained physician and longevity expert who wrote Invincible, shares a personal science-backed take on aging. She talks about why genes are not destiny. She questions popular biohacking. She highlights sleep, blood sugar, hormones, and personalized medicine as the keys to aging smarter.
Apr 22, 2026 • 23min
Take a Month Off and See Who You Become
A radical 30-day experiment in disappearing with no plan, devices, or expectations. A ritual of prewritten eulogies and strict rules to force real disconnection. Practical prep around health, meds, and telling the world you will be unreachable. An invitation to slow down, quit productivity goals, and explore what emerges when structure drops away.
