The Midlife Chrysalis

Chip Conley
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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. 1 DAY AGO

    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

  2. 3 DAYS AGO

    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

  3. 6 DAYS AGO

    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

  4. 4 FEB

    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

  5. 2 FEB

    How a Panic Attack Sparked a Midlife Awakening | Dan Harris

    He had everything going for him, until his body shut him down on live TV. In this episode, Dan Harris sits down with Chip Conley for a warm, honest conversation about ambition, anxiety, and what really changes in midlife. Dan opens up about the panic attack that forced him to slow down, his years inside high-pressure newsrooms at ABC, and the quiet realization that productivity, without presence, was costing him more than it gave. What follows is not a polished mindfulness pitch, but a deeply human reflection on letting go, growing wiser, and redefining success in the second half of life.  In this conversation, you’ll hear Dan reflect on: Why anxiety and ambition are often two sides of the same coinHow meditation helped him step out of the productivity trap—not optimize itWhat he had to release after becoming outwardly “successful”Why midlife is better understood as a chrysalis, not a crisisHow relationships, presence, and character shape a more meaningful future If you’re navigating midlife, questioning old definitions of success, or simply craving a more spacious way to live, this conversation will feel like sitting down with two thoughtful friends who’ve been there. Watch now and join the conversation.  Timestamps: 02:17 Defining midlife and Dan Harris’s journey 03:50 Panic attack on live TV 05:31 From panic attack to meditation 06:46 Family background and anxiety 08:31 Decade between crisis and mindfulness advocacy 09:33 Therapy spirituality and discovering meditation 13:37 Writing 10% Happier 14:22 Origin of the 10% happier idea 16:43 Science and benefits of meditation 19:47 Skepticism identity and cognitive dissonance 22:14 Life after the book’s success 26:06 Productivity versus presence 29:47 Burnout hyper productivity and 360 review 33:06 Letting go of roles and redefining life 35:59 Midlife as chrysalis not crisis 39:36 Favorite meditation practices 42:09 Wisdom midlife and modern elderhood 45:08 Character skills in the age of AI 47:07 Personal wisdom and life lessons 49:10 Closing reflections and goodbye  Learn more about MEA at ⁠https://www.meawisdom.com/

    50 min

  6. 30 JAN

    When Cancer Forces a Life Reset in Midlife | Caryn Lerman

    Cancer doesn’t just affect your health. It changes how you see yourself and your life. In this warm and honest conversation, Chip Conley sits down with Caryn Lerman to explore the emotional side of cancer that often goes unspoken. Together, they talk about identity shifts, caregiving, and what it really means to move through the messy middle of midlife after a diagnosis.  In this episode, you’ll hear: How cancer reshapes identity, not just the bodyWhy caregivers carry an invisible emotional loadWhat it means to live intentionally after cancerHow vulnerability can become a source of strength Watch the full episode and join us for a thoughtful, compassionate conversation about healing, meaning, and becoming who you are now.  Timestamps: 04:14 Psychology of cancer survivors and caregivers 06:47 Identity loss and existential impact of cancer 07:53 Chip’s cancer diagnosis and early denial 13:13 Regret fear, and emotional processing 16:23 Cancer as a teacher and life priorities 19:39 Anxiety treatment and living with uncertainty 20:33 Staying busy to avoid difficult emotions 24:16 Values family and vulnerability 26:01 Strength identity and emotional suppression 28:01 Caregivers and lack of support systems 30:10 Invisible burden of caregiving 32:06 Emotional catharsis and healing journey 35:32 Caregiver and survivor archetypes 38:49 Inside the cancer thrivers workshop 42:18 Identity mapping and letting go 43:41 Meaning values and intentional living 45:42 How friends can best support someone with cancer 47:26 Cancer is not a linear journey 48:28 Wisdom bumper sticker advice 51:53 Growth outside the comfort zone  Learn more about MEA at https://www.meawisdom.com/

    58 min

  7. 28 JAN

    Why Rituals Matter More Than Routines in Midlife

    What if the way you start your morning is quietly shaping how your whole day feels? Chip Conley sits down with Derek Gehl to explore why so many midlife routines start to feel empty and how turning them into simple, meaningful rituals can bring more calm, clarity, and purpose to everyday life. Together, Chip and Derek share: Why routines can feel mechanical, while rituals help us feel present and changedHow to gently layer meaning onto things you already do, like showering or stretchingWhy small morning rituals can boost mood, energy, and emotional well-beingHow affirmations work best when they’re personal, specific, and emotionally realEasy ways to create micro-rituals that set a better tone for your day If midlife has you longing for more intention without adding more to your plate, this episode is a friendly invitation to start small and start with your morning. Give it a listen, try one simple ritual this week, and notice what begins to shift.  Timestamps: 02:12 Morning rituals vs routines 02:28 Routine vs ritual 04:00 Shower meditation prayers 05:48 Affirmations and new stretching ritual 11:21 The impact of morning rituals12:27 Accountability and consistency 14:01 Rituals as landmarks and micro rituals 15:24 How to create your own rituals 17:07 Science and specificity of affirmations  Learn more about MEA at ⁠https://www.meawisdom.com/

    18 min

  8. 26 JAN

    How Ritual, Awe, and Community Bring Midlife Back to Life | Christine Sperber

    In this episode, Chip Conley sits down with Christine Sperber, co-founder of MEA and master experience designer, to explore how awe, ritual, and community can bring us back to life in midlife. Drawing from ski town culture, life in Baja, and years of building transformational experiences, Christine offers a hopeful reframe of aging as something to design, not fix. In this conversation, Chip and Christine explore: Why purpose matters more than productivity in midlifeHow simple rituals create meaning, resilience, and belongingWhat nature, movement, and community teach us about vitalityWhy transitions like perimenopause and loss call for compassion, not hustleIf midlife feels like a pause, a question mark, or an invitation to something more, this episode will leave you feeling seen, grounded, and hopeful.Listen now and rediscover what it means to feel fully alive in midlife.  Timestamps: 03:22 Christine Sperber’s background 06:55 Leaving Colorado for Baja 08:49 First experience of Baja and Pescadero 10:59 Freedom and living in rhythm with nature 15:15 Experience design and creating meaningful gatherings 17:48 Baking bread as ritual and collective practice 22:14 Origin story of MEA 24:02 Early doubts and building a local economy 26:07 Lessons from the first MEA beta cohorts 30:38 Ski towns, purpose, and longevity research 33:46 Aging, vitality, and midlife perspective 40:49 Introversion, ritual, and reclaiming time 46:19 Third vault conversations and authentic community 48:26 Moral beauty as a pathway to awe 54:11 Transformation through deep connection 56:19 Designing belonging and social bonds 57:28 Wisdom bumper sticker Learn more about MEA at ⁠https://www.meawisdom.com/

    1h 4m
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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
    68
  • Rating
    Clean
  • Copyright
    © Chip Conley
  • Show Website
    The Midlife Chrysalis

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