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
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.
Feb 16, 2026 • 1h 3min
Why Midlife Men Struggle with Identity & Purpose Today | Greg Scheinman
Greg Scheinman, entrepreneur and founder of Midlife Male who reinvented his life after a midlife breakdown. He recounts career pivots and a tipping point at 47. Conversations cover modern masculinity, identity loss in midlife, turning crisis into reinvention, marriage and parenting tensions, and practical frameworks like the Six Fs for rebuilding purpose.
6 snips
Feb 13, 2026 • 58min
Why Friendship Becomes the Most Important Skill in Midlife | Jeff Hamaoui
Jeff Hamoui, MEA co-founder and community builder who created Baja Sage, speaks about redesigning life around friendship and belonging. He explores friendship as a practiced skill, contrasts transactional living with deep connection, and explains how intentional community and social architecture support a generative second chapter in midlife.
Feb 11, 2026 • 21min
What Great Mentors Do Differently in Midlife
Conversations about how mentorship changes in midlife and why asking better questions beats having all the answers. Stories from Airbnb and intergenerational leadership show learning goes both ways. Four stages to become a modern elder and the contrast between librarian-style and confidant-style mentorship are explored. Practical tips on structuring lasting, respectful mentoring relationships are shared.
24 snips
Feb 9, 2026 • 53min
Why Wisdom Matters More Than Knowledge in Midlife | Eric Weiner
Eric Weiner, bestselling author and inquisitive traveler who tests ideas in real life. He explores why midlife nudges us toward wisdom, contrasts knowing more with living better, and draws on philosophers from Socrates to Thoreau. Expect playful, practical talk about wonder, humility, generosity, and simple habits for navigating change and uncertainty.
8 snips
Feb 6, 2026 • 1h 3min
Losing Everything to Find Purpose: Aithan Shapira’s Midlife Shift
Aithan Shapira, artist, MIT lecturer and leadership facilitator who blends creative practice with adult development. He recounts losing his studio and reinventing his life. Talks about practice as a way of life. Explores midlife as a transformative chrysalis. Describes the three stages of transition and how to preserve identity while letting go.
Feb 4, 2026 • 33min
Stuck at 50? How to Make a Midlife Career Change Without Starting Over
Chip Conley, founder of the Modern Elder Academy and hospitality entrepreneur, shares his midlife reinvention playbook. He reframes midlife as mid-career. He explains iterative pivots, bridge jobs, portfolio and encore careers. He outlines four pathways to purpose and how identity shifts and community support fuel change.
Feb 2, 2026 • 50min
How a Panic Attack Sparked a Midlife Awakening | Dan Harris
Dan Harris, former ABC anchor turned meditation advocate and author of 10% Happier, opens up about a live-TV panic attack that redirected his life. He talks about anxiety tied to ambition, how meditation pulled him out of the productivity trap, the 360 review that forced big life changes, and why midlife can be a chrysalis for deeper presence and character.
Jan 30, 2026 • 58min
When Cancer Forces a Life Reset in Midlife | Caryn Lerman
Caryn Lerman, psychologist and cancer center director known for psycho-oncology work, discusses how cancer reshapes identity and the invisible emotional load of caregiving. They explore staying present versus avoidance, values and family reprioritization, transformative healing experiences, and practical ways friends can support someone through the non-linear journey of illness.
8 snips
Jan 28, 2026 • 18min
Why Rituals Matter More Than Routines in Midlife
A conversation about turning mechanical morning routines into small, meaningful rituals that bring calm and purpose. They explore shower meditations, prayer-like mantras, and a stretching plus affirmation practice. The discussion covers habit-stacking to make rituals stick and how to craft specific, emotionally true affirmations. Listeners are invited to try one simple micro-ritual to shift their day.
