The Midlife Chrysalis

Chip Conley
  • 5.0 (51)
  • SELF-IMPROVEMENT
  • UPDATED WEEKLY

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.

  1. 21H AGO

    Your Brain on Art: Why Midlife Needs Creativity More Than Ever | Susan Magsamen & Ivy Ross

    Midlife isn’t a crisis. It’s an invitation to come alive again. In this episode of Midlife Chrysalis, Chip Conley is joined by Susan Magsamen, a neuroscientist at Johns Hopkins, and Ivy Ross, Chief Design Officer at Google, for a warm, eye-opening conversation about why creativity is essential to being human, especially in midlife. Drawing from their book Your Brain on Art, they share how art, play, and sensory experiences quietly support brain health, emotional balance, and a deeper sense of meaning in a world obsessed with productivity and speed. You’ll hear why: Creativity is hard-wired into our biology, not reserved for “artists”Midlife is a powerful moment to rediscover curiosity, play, and makingSmall creative acts can reduce stress and help us feel more aliveArt may be one of the healthiest counterweights to burnout and AI The second half of life isn’t about doing more, it’s about sensing more, feeling more, and reconnecting with what truly matters. 👉 Watch now and let midlife become a chrysalis, not a cage. Timestamps: 13:35 Guest backgrounds and journeys 18:36 What Your Brain on Art is really about 21:25 Neuroaesthetics and brain science 23:54 Why creativity is essential for health 24:24 How to rebuild creativity in midlife 29:14 Art, neuroplasticity, and medicine 34:32 Creativity inside Google 39:18 Digital literacy, nature, and balance 41:35 Personal midlife transformation stories 45:30 Resilience through illness and change 49:08 Life wisdom and defining moments 55:51 Final reflections and closing Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeChrysalis #YourBrainOnArt #CreativityAndAging #MidlifeWellbeing #Neuroaesthetics #BrainHealth #CreativityForAdults #MidlifeGrowth #ArtAndScience #HealthyAging #MentalHealthMidlife #PurposeInMidlife #CreativeLiving #SecondHalfOfLife #MidlifeInspiration

    51 min

  2. 2D AGO

    Why Midlife Friendships Stop Working & How to Fix Them

    Ever notice how some friendships don’t end, they just stop deepening?You still care about each other, but the conversations feel thinner than they used to. In midlife, that quiet shift is more common than we admit. In this Wisdom Wednesday episode, Chip Conley, founder of MEA, joins Derek Gehl for a warm, honest conversation about friendship in the second half of life: why it changes, why it matters more than ever, and how it can grow again. What you’ll take away: Friendship is a practice, not a personality traitMost of us outgrow conversations, not peopleDepth and vulnerability create real connectionReaching out — even after years — can reopen meaningful bondsIf you’ve ever wondered how to build friendships that actually nourish you as you age, this conversation is for you. Listen now and discover how midlife friendships can become richer, not smaller.  Timestamps: 00:13 Friends in midlife and outgrowing friendships 00:45 Friendship as a practice 02:10 Reconnecting with old friends 04:20 Outgrowing conversations not people 06:00 Depth vulnerability and the three vaults 09:40 Why friendship requires depth 10:48 Men opening up emotionally 13:05 Leading with vulnerability 13:58 Creating deeper conversations naturally 15:48 Different levels of friendship 16:39 Couples growth and shared language 17:37 Transactional vs real friends 18:02 How to rebuild friendships in midlife 20:13 Closing thoughts and wrap up  Learn more about MEA at ⁠https://www.meawisdom.com/#MidlifeFriendships, #MidlifeConnection, #FriendshipAfter40, #SecondHalfOfLife, #MeaningfulRelationships, #EmotionalIntelligence, #PersonalGrowth, #SocialConnection, #AuthenticLiving, #MidlifeWisdom, #LifeTransitions, #ProAging, #ModernAging, #HumanConnection, #WisdomWednesday

    20 min

  3. 4D AGO

    Why Midlife Men Struggle with Identity & Purpose Today | Greg Scheinman

    Ever wonder what happens when “success” still feels empty? At 47, Greg Scheinman looked like he had it all, career, family, success, yet felt completely lost. That moment pushed him to reinvent himself and create Midlife Male, a movement helping men find purpose, strength, and authenticity in midlife. In this episode, we dive into what modern masculinity really means, why so many men struggle with identity and purpose, and how to turn a midlife crisis into a life by design. Tune in to learn how Greg turned breakdown into breakthrough and how you can too.  Timestamps: 00:00 Introduction 00:24 Early Life & Family Loss 02:38 Working for Harvey Weinstein 05:03 From Film to Entrepreneurship 08:15 Lessons on Curiosity & Reinvention1 0:53 Identity Crisis at 40 13:29 Entering the Insurance Industry 15:16 Building a PBS Show 16:57 Struggling with Identity 22:20 Tipping Point at 47 24:33 Creating Midlife Male 26:30 Marriage Problems & Masculinity 30:34 Why He Built Midlife Male 38:48 The Modern Midlife Male Dilemma 41:37 Conviction, Curiosity & Courage to Speak 45:00 The Six F’s of Life & Finding Success 49:06 Raising Sons Today 54:56 Wisdom Bumper Sticker 57:07 Learning to Be Both Hard & Soft  Learn more about MEA at ⁠https://www.meawisdom.com/ #GregScheinman #MidlifeMale #MidlifeChrysalisPodcast #ChipConley #ModernMidlifeMan #MenInMidlife #MidlifeReinvention #MidlifeIdentity #MensMentalHealthAwareness #RedefiningMasculinity #LifeByDesign #EntrepreneurInMidlife #MidlifeWisdom #PurposeBeyondSuccess #FromCrisisToGrowth

    1h 3m

  4. FEB 13

    Why Friendship Becomes the Most Important Skill in Midlife | Jeff Hamaoui

    Midlife rarely falls apart all at once. It slowly grows quieter, fewer close friendships, less community, more doing and less belonging. In this episode of Midlife Chrysalis, Jeff Hamaoui, MEA co-founder and community builder, reflects on how midlife invited him to redesign his life around friendship, connection, and community. In a warm, thoughtful conversation, Jeff shares: - Why friendship is a skill we can practice and deepen - How transactional living erodes real connection - Why community is essential to well-being in midlife - How choosing a second chapter starts with belonging If you’re navigating midlife and craving deeper connection, this episode offers clarity, comfort, and perspective. 👉 Watch now and explore what truly supports your next chapter. Timestamps: 03:16 Jeff’s background and international upbringing 05:02 Growing up in Venezuela and reflections on the country 06:38 Leaving the Bay Area and the midlife turning point 09:56 Comparison culture and pressure in the Bay Area 11:02 Transactional vs relational relationships 12:39 Friendship as a practice 15:44 Core lessons on listening and asking better questions 18:49 Going first and the mindset of friendship 22:14 Friendship health longevity and happiness 24:23 Resistance to wellness and personal growth 28:44 Self-awareness pattern recognition and wisdom 31:46 Midlife transitions and choosing a second adulthood 38:10 Midlife crisis vs midlife chrysalis 40:29 MEA as a call to action 43:55 Creating community and the origins of Baja Sage 45:09 Community vs real estate development 51:23 Social architecture and relational living 52:32 Wisdom as metabolized experience Learn more about MEA at ⁠https://www.meawisdom.com/ #friendshipasaskill #midlifecommunity #relationalliving #secondadulthood #midlifefriendship #communitybydesign #transactionaltorelational #modernelder #mea #chipconley #jeffhamaoui #intentionalcommunity #midlifebelonging #socialconnection #humanconnection

    58 min

  5. FEB 11

    What Great Mentors Do Differently in Midlife

    Most of us grow up thinking mentorship means having the answers. In midlife, we learn it’s really about asking better questions. In this Wisdom Wednesday episode, Derek and Chip explore how mentorship evolves when experience meets curiosity. Drawing on stories from Airbnb, intergenerational leadership, and lessons from unlikely teachers, Chip shows why the best mentors are still learning. In this conversation, you’ll discover: • Why great mentorship is a two-way exchange, not top-down advice • How modern elders learn alongside younger generations • The difference between a librarian mentor and a confidant mentor • Why respect and curiosity matter more than credentials • How asking the right questions creates real growth at work and in lifeIf you’re navigating midlife, leading across generations, or rethinking how you share your wisdom, this episode is for you. Watch now and join us for Wisdom Wednesday.  Timestamps: 01:58 Why mentorship matters in midlife 04:16 Digital natives vs digital immigrants 05:11 The respect gap in mentorship 06:20 Defining wisdom and lived experience 07:10 Four stages of becoming a modern elder 08:22 Appreciative inquiry and powerful questions 10:30 Librarian mentor vs confidant mentor 12:20 Chip Conley and Herb Kelleher mentorship story 14:20 How confidant mentorship builds confidence 15:45 How to structure a healthy mentorship 16:53 Mentors vs coaches explained 18:35 The mentorship gap and retention impact 18:51 How to start mentoring at midlife 20:55 Mentorship and renewed purpose 21:51 Final reflections and closing  Learn more about MEA at ⁠https://www.meawisdom.com/

    21 min

  6. FEB 9

    Why Wisdom Matters More Than Knowledge in Midlife | Eric Weiner

    We’re surrounded by information but many of us still feel unsure about how to live well. This episode gently explores why midlife pulls us toward wisdom, not more answers. Chip Conley is joined by bestselling author Eric Weiner (The Geography of Bliss, Man Seeks God, The Socrates Express), a curious guide who’s spent years learning from philosophers, cultures, and lived experience. Together, they talk about what ancient wisdom can teach us about modern life—especially when certainty starts to fall away.  In this conversation, you’ll hear: Why midlife naturally turns us into philosophersThe difference between knowing more and living betterHow thinkers like Socrates, Thoreau, and Marcus Aurelius offer practical guidanceWhy wonder, humility, and generosity matter more than expertiseSimple ideas that help us navigate change, relationships, and uncertainty This is a warm, thoughtful, and often playful conversation about slowing down, asking better questions, and learning how to live with more clarity and meaning. Watch now and step into the wisdom midlife is inviting you to explore.  Timestamps: 04:21 Welcome to Midlife Chrysalis 04:59 Writing with humility and vulnerability 07:02 Book titles and framing ideas 08:34 Geography of Bliss origin story 12:31 Favorite places and soul place 13:54 Ben Franklin and usefulness 18:31 Writing about God and belief 21:44 Geography of Genius and creativity 23:30 Introducing The Socrates Express 24:10 Knowledge vs wisdom 27:23 What philosophy really is 30:38 Wonder vs curiosity 34:40 Stoicism and modern relevance 37:33 Philosophers that resonated most 40:53 Thoreau and learning how to see 44:52 Why philosophy matters in midlife 49:20 Wisdom bumper stickers 52:26 Closing and Santa Fe workshop  Learn more about MEA at ⁠https://www.meawisdom.com/

    53 min

  7. FEB 6

    Losing Everything to Find Purpose: Aithan Shapira’s Midlife Shift

    What if losing everything was the only way to truly find yourself? MIT lecturer and artist Aithan Shapira shares how the collapse of his art career became the catalyst for profound reinvention. He explains why midlife isn’t about decline but transformation , a time to practice letting go, reframe purpose, and reconnect with what matters most. If you’re in a season of change, this episode will help you see midlife as your greatest canvas yet.  Timestamps: 00:00 Intro 01:17  Meet Aithan Shapira 04:05 Living Between Worlds 05:32 MIT, NASA & Global Clients 06:32 Practice as a Core Principle 07:46 Cubism & Midlife Transition 11:00 Life as a Practice vs Routine 14:05 Practice vs. Ritual 15:30 Aithan’s Views on Midlife 20:55 Accelerating Internal Change 25:37 The Three Stages of Transition 27:59 Coping With Freefall 32:59 What Needs to Be Preserved 36:11 Identity in Retirement & Second Half of Life 38:18 Aithan’s Own Chrysalis Story 46:21 Long Life Learning 53:21 The Wisdom of Midlife 55:58 Aithan’s Bumper Sticker Wisdom 59:07 Closing Thoughts  Learn more about MEA at ⁠https://www.meawisdom.com/

    1h 3m

  8. FEB 4

    Stuck at 50? How to Make a Midlife Career Change Without Starting Over

    What if midlife isn’t the end of your career story but the smartest place to rewrite it? In this episode of Wisdom Wednesday, Chip Conley joins Derek Ghel to unpack what really happens when people feel stuck at midlife, and why career change after 50 doesn’t require starting over or burning everything down. Drawing on his journey from boutique hotels to Airbnb to founding the Modern Elder Academy, Chip offers a grounded, hopeful roadmap for reinvention that actually works in the real world.  In this episode, you’ll learn: Why midlife can be the most strategic time to change careers, not the riskiestHow to use small, iterative steps and bridge jobs instead of all-or-nothing leapsThe four pathways to purpose that reveal what’s next for youWhy portfolio careers and encore paths are becoming the new normalHow identity, fear, and “being a beginner again” shape midlife transitions If you’re questioning your work, your direction, or what the next chapter should look like, this conversation will help you reframe what’s possible. Watch the episode, reflect on what’s calling you next, and take the first small step forward.  Timestamps: 00:41 Chip Conley’s career journey 03:10 Rethinking age and career length 05:23 Retirement vs staying relevant 10:43 Taking small iterative steps 13:25 Entrepreneurship after 50 16:33 Bridge jobs and testing ideas 18:26 A real midlife pivot story 19:18 Purpose, community and wellness 23:29 Identity fear and becoming a beginner 27:17 Why people come to MEA 31:47 Final thoughts and wrap-up  Learn more about MEA at ⁠https://www.meawisdom.com/

    33 min
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5
out of 5
51 Ratings

About

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.

Information

  • Creator
    Chip Conley
  • Years Active
    2025 - 2026
  • Episodes
    72
  • Rating
    Clean
  • Copyright
    © Chip Conley
  • Show Website
    The Midlife Chrysalis

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