The Midlife Chrysalis

Chip Conley
  • 5.0 (57)
  • 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. 6H AGO

    Feeling Lost? Use Inner Tracking to Find Your Path| Lee Johnson

    Midlife can feel confusing, off track, or quietly unsettled, and you’re not the only one feeling it.  In this episode of Midlife Chrysalis, Lee Johnson, a mindfulness guide and teacher, shares his journey from ranch life to guiding others through mindfulness and “inner tracking,” offering a grounded and deeply human perspective on finding your way without a clear plan.  Here’s what you’ll take away: • Why feeling lost in midlife is often a turning point, not a problem • What inner tracking is and how it helps you make aligned decisions • How to trust your path even when nothing feels certain • Why disconnection is so common and how to reconnect with yourself • A simple awareness practice you can use right away  If midlife has you questioning your direction, this conversation will bring clarity and calm. Watch now and start finding your way back.  Timestamps: 00:00 Introduction and welcome 00:22 Lee Johnson’s origin story 01:10 Early influences and spiritual mentors 02:56 Energetic imprint and childhood experiences 04:00 Alaska years and connection to nature 05:30 Holistic health and yoga ashram journey 07:09 Life at Kripalu and spiritual growth 08:30 Native American teachings and Vipassana 09:57 Regenerative agriculture and land philosophy 12:09 Leaving the ranch and searching for purpose 14:24 Joining the ranch and new beginnings 17:17 Transition to teaching and inner work 19:53 Self-doubt and stepping into leadership 21:24 Discovering guided meditation and teaching 22:53 Inner tracking explained 27:37 Intuition and life path insights 30:23 “I don’t know where I’m going…” 31:33 Observations on midlife transformation 35:28 Disconnection and modern life 38:55 Guided inner tracking exercise 44:03 Workshops and teaching approach 47:29 Collaboration with partner Melanie 48:26 Life advice and awareness practice 52:57 Turning wounds into wisdom  Learn more about MEA at ⁠https://www.meawisdom.com/  #MidlifeChrysalis #MidlifeTransformation #FindYourPurpose #LifeTransitions #InnerWork #MindfulnessPractice #PersonalGrowth #MidlifeJourney #SelfDiscovery #EmotionalWellbeing #LifeDirection #SpiritualGrowth #ReconnectWithYourself #InnerPeace #PurposeInMidlife

    1h 2m

  2. 2D AGO

    Stuck Between Aging Parents and Grown Kids in Midlife?

    You’re taking care of your parents. You’re supporting your kids. But who’s taking care of you? In this Wisdom Wednesday episode, Derek Gehl sits down with Chip Conley to unpack the reality of the sandwich generation and why midlife can feel more overwhelming than ever.  Chip shares key insights on: • The real emotional cost of caregiving • Why this stage of life feels heavier today • How to build a support system that actually helps • Why protecting time for yourself is essential A clear, honest conversation for anyone feeling stretched thin in midlife. 👉 Watch the full episode and subscribe for more real conversations like this.  Timestamps: 00:20 The sandwich generation 01:24 Chip’s caregiving experience 02:49 Importance of support system 04:25 Emotional toll of caregiving 07:31 Having kids later in life 09:27 Adult kids moving back home 10:27 Longevity and caregiving challenges 12:56 Health span vs. lifespan 15:12 Independence and interdependence 16:50 Longevity manifesto explained 18:06 Science vs art of longevity 19:03 Blue Zones lifestyle insight 20:18 Caregiver workshop challenge  Learn more about MEA at ⁠https://www.meawisdom.com/  #SandwichGeneration #MidlifeStruggles #Caregiving #AgingParents #MidlifeCrisis #CaregiverLife #EmotionalBurnout #FamilyCare #Longevity #Healthspan #MidlifeSupport #PersonalGrowth #StressManagement #LifeTransitions #ChipConley

    19 min

  3. 4D AGO

    Leading in Chaos: How to Stay Grounded Under Pressure | Amy Elizabeth Fox

    What if the chaos in your life isn’t the problem… but the turning point? In this episode, Amy Elizabeth Fox, leadership expert and co-founder of Mobius, explains why today’s pressure, uncertainty, and stress are actually pushing us to grow in a deeper way. Through her work with top executives and her own life story, she shows what it really takes to lead and stay grounded when everything feels unstable. Here’s what you’ll learn: Why people fall back into old patterns under stressHow your past shapes the way you lead and live todayWhy success in midlife can feel empty and how to change thatWhat it really means to lead in chaosWhy healing and self-awareness matter more than ever This is not just about leadership. It’s about understanding yourself on a deeper level. 👉 Watch now if you feel overwhelmed, stuck, or ready for something more. Timestamps: 2:43 What is vertical development 4:10 Personal and professional growth merge 5:29 Midlife leadership struggles 8:24 Early life challenges and illness 10:37 Genetic disease and urgency 11:35 Spiritual and environmental work 13:21 Leadership and spirituality connection 15:35 Corporate transformation and culture 19:29 Freedom after adversity 21:08 Feminine leadership in business 22:55 Leading in chaos introduction 24:40 Spiritual path and teachers 27:03 Spirituality in action 28:42 Chaos and leadership today 31:51 Key principles for leading in chaos 35:00 Corporate reality and hope 37:38 Midlife transformation insights 40:25 What improves with age 41:59 Freedom in midlife 46:28 From receiving to giving 47:24 Final wisdom and life philosophy ABOUT AMY ELIZABETH FOX: Bio: Amy Elizabeth Fox is the co-founder and CEO of Mobius Executive Leadership, a global transformational leadership firm. For over twenty years, she has advised senior leaders in eminent professional services firms and Fortune 500 companies on leadership and culture change. In 2026, she co-authored Leading in Chaos with Nicholas Janni and is widely regarded as an expert in vertical development and trauma-informed work in organizations. Read the Full Bio Links: Leading in Chaos Book Website: https://leadinginchaosbook.com/ Mobius Website: http://www.mobiusleadership.com/ Amy’s Website: http://www.amyelizabethfox.com/ ABOUT LEADING IN CHAOS Book Overview: Nicholas Janni and Amy Elizabeth Fox’s forthcoming book, Leading in Chaos, argues that in an era of polycrisis and sustained uncertainty, leadership requires next practice — a fundamentally different inner operating system grounded in deeper human intelligence. It reframes leadership as an embodied, developmental practice, calling leaders to act with coherence, presence, and integrity amid ongoing disruption. Because, in their words, “chaos is the new black.” Social media posts: LinkedIn postInstagramFacebook Learn more about MEA at ⁠https://www.meawisdom.com/ #Leadership #LeadingInChaos #PersonalGrowth #SelfAwareness #EmotionalIntelligence #MidlifeGrowth #BurnoutRecovery #StressManagement #InnerWork #HighPerformance #MindsetShift #ExecutiveLeadership #PsychologyOfSuccess #WorkplaceCulture #LeadershipDevelopment

    56 min

  4. APR 3

    She Told 80,000 Employees the Truth She Hid Her Entire Life | Katherine Dudtschak

    She had the perfect life - career, family, success - and a secret she kept hidden for decades. In this episode, Katherine Dudtschak, a former top banking executive, opens up about coming out at 50, telling 80,000 employees, and risking everything to finally live in alignment with who she truly is.It’s an honest, deeply human story about what happens when you spend years living the life you’re “supposed” to live, and what it takes to finally choose your own.  You’ll hear: Why even a “perfect” life can feel incompleteHow suppressed identity shows up over timeThe moment everything became impossible to ignoreWhat it really takes to start over without losing yourselfWhy vulnerability can become your greatest strength👉Watch now! It’s never too late to choose yourself.  Timestamps: 2:02 Katie’s background and corporate success 3:36 Feeling incomplete despite success 5:24 Childhood struggles and proving herself 7:44 Midlife awakening begins 9:07 Family history and trauma 12:31 Suppressed identity resurfaces 15:28 Career success but emotional collapse 17:53 Defining gender identity moment 20:57 Mental health crisis and turning point 21:36 Commitment to truth and coming out 23:21 Coming out to 80,000 employees 27:38 Team reaction and support 28:42 Unexpected outcome and acceptance 29:24 Advice on major life changes 31:48 Power of vulnerability 33:09 Building the right support system 36:25 Importance of time and process 38:48 Career transition and new identity 41:52 New purpose and leadership vision 43:48 CEO role and serving older adults 46:20 Launching Sincerely and storytelling mission 49:12 Vision for a more human world 52:22 Core message reclaim your essence 54:37 The three selves explained Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeTransformation #ComingOutStory #LifeAfter50 #FindYourself #AuthenticLiving #GenderIdentity #PersonalGrowth #LifeChange #MentalHealthJourney #StartOver #BeYourself #SelfDiscovery #LGBTQStories #EmotionalHealing #PurposeDrivenLife

    1h 1m

  5. APR 1

    Why So Many Men Lose Friends in Midlife (And How to Fix It)

    What if the biggest factor for a longer, happier life isn’t health, but friendship? In this Wisdom Wednesday episode, Chip Conley joins Derek Gehl to explore why so many people, especially men, struggle with connection in midlife, and how to change that. Here’s what you’ll learn: Why friendship is the #1 predictor of longevityThe difference between real vs transactional relationshipsWhy men often lack deep connection and how to fix itThe one simple habit that can reignite old friendships If you’ve been feeling disconnected, this conversation will resonate more than you expect. 👉 Watch now and reconnect with what really matters Timestamps: 00:00 Intro and Yellowstone ranch vibe 01:24 Building the ranch experience 03:07 Why connection matters for longevity 04:09 Why men struggle with friendships 06:32 Why are women more drawn to workshops 08:32 Transactional vs real friendships 12:07 Vulnerability and male friendship barriers 13:51 Story about father finding community later in life 14:55 Friendship and regrets at the end of life 16:38 Marriage pressure and need for male friendships 17:59 Friendship as a daily practice 18:46 Introverts vs extroverts and connection 19:50 Simple action to rebuild friendships 20:24 Workshops and final takeaway Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeCrisis #FriendshipMatters #MensMentalHealth #Loneliness #MidlifeMen #SocialConnection #SelfDevelopment #EmotionalHealth #MentalWellbeing #BuildBetterRelationships #PersonalGrowth #LifeInMidlife #ConnectionMatters #ModernElder #HealthyRelationships

    19 min

  6. MAR 30

    Death, Belonging, and What It Means to Be Human | Sebastian Junger

    He was bleeding out… and didn’t even know he was dying. In this powerful conversation, war journalist and bestselling author Sebastian Junger shares the moment he came face-to-face with death and what he discovered on the other side. From a sudden internal hemorrhage to a near-death experience that challenged everything he believed, Junger takes us deep into the edge between life and death… and back again. But this episode isn’t just about dying, it’s about how to live. Here’s what you’ll take away: Why facing death can completely reset your prioritiesWhat near-death experiences reveal about consciousnessWhy modern life is making us feel more alone than everThe hidden power of “tribe” and human connectionA simple question that can change how you live every day This isn’t just about dying. It’s about finally understanding how to live. 👉 Watch now. Timestamps: 01:45 Thoughts on death and accepting mortality 03:50 Aneurysm story and war reporting background 06:34 Internal bleeding and race to the hospital 08:00 Near-death vision and seeing his father 11:28 Emergency procedure and survival 13:36 ICU realization and trauma of almost dying 15:50 Sacred vs scary perspective on death 18:27 Atheism, consciousness, and reality questions 21:20 Science vs mystery of near-death experiences 26:11 Shared patterns in near-death experiences 30:45 Personal transformation after near-death 33:10 Living with awareness of mortality 36:40 Rituals of death and cultural perspectives 38:41 Tribe, belonging, and modern isolation 42:04 Solutions for rebuilding the connection 45:24 Life lessons and meaning of tribe and love Learn more about MEA at ⁠https://www.meawisdom.com/ 👉To learn more about Junger's tribe, check out this link: https://sebastianjunger.substack.com/ #SebastianJunger #SebastianJungerInterview #NearDeathExperience #NearDeathExperienceStory #WhatHappensWhenYouDie #LifeAfterDeath #Consciousness #DeathAndDying #MeaningOfLife #HumanConnection #Belonging #Tribe #ModernLoneliness #PsychologyOfBelonging #PersonalGrowth

    53 min

  7. MAR 27

    How an Anarchist Built One of America’s Most Unique Businesses | Ari Weinzweig

    Anarchism isn’t chaos. It might be the key to better leadership. In this thought-provoking episode, Chip speaks with Ari Weinzweig, co-founder of Zingerman’s, a company that grew from a $22,000 deli into an $80M family of businesses built on an unconventional idea: trust people, give them dignity, and rethink hierarchy. Ari shares the surprising philosophy that shaped Zingerman’s culture and explains why many traditional leadership models miss what really motivates people. In this episode, you’ll learn: What anarchism can teach us about leadershipWhy dignity should be the foundation of every workplaceThe beliefs that quietly shape every leadership decisionWhy there is no single “number one rule” in business This conversation will challenge how you think about leadership, organizations, and human potential. 👉 Watch the full episode to discover the radical philosophy behind Zingerman’s success. Timestamps: 05:52 Ari Weinzweig and long friendship 06:47 Ari’s background studying anarchism 09:42 Discovering a passion for restaurant work 11:26 The origin story of Zingerman’s 13:16 Growth of the Zingerman’s businesses 13:56 What anarchism means for leadership 18:46 The importance of leadership philosophy 23:45 Values, beliefs, and mission in business 24:46 The Revolution of Dignity concept 33:45 Advice to his younger self 35:48 Life skills vs. traditional education 37:03 Creation of ZingTrain 42:52 Supporting employees to succeed 44:24 Radical wisdom and authentic leadership 46:00 The concept of deep understanding Learn more about MEA at ⁠https://www.meawisdom.com/ 👉 To learn more about Ari’s latest book and the Apricots for Dignity and Democracy initiative he mentioned in the podcast, check out these links: From Founder to Future: A Business Roadmap to Impact, Longevity, and Employee Ownership https://a.co/d/0bBYKIIl https://undergroundshirts.com/groups/apricots-for-dignity-and-democracy #Leadership #Anarchism #AnarchistLeadership #BusinessLeadership #LeadershipPhilosophy #ServantLeadership #WorkplaceCulture #Zingermans #AriWeinzweig #ModernLeadership #FutureOfLeadership #EntrepreneurMindset #OrganizationalCulture #RadicalLeadership #BusinessPodcast

    55 min

  8. MAR 25

    Men vs Women in Midlife: The Struggles No One Warns You About

    Most people imagine a midlife crisis as sports cars, bad decisions, and dramatic life changes. But what if midlife is actually something much deeper and more meaningful? In this episode of Midlife Chrysalis, Chip Conley explores what really happens during midlife and why men and women often experience it differently. Chip shares insights from years of research and thousands of midlife transitions, revealing the real challenges people face in their 40s, 50s, and beyond. In this conversation, you’ll learn: Why midlife is often a feeling of being stuck, not a crisisThe hidden struggles men face, including hormonal decline, loneliness, and loss of purposeWhy many women experience invisibility and financial pressure in midlifeHow menopause, andropause, and identity shifts reshape relationships and self-confidenceWhy the real question in midlife becomes “How will you invest your wisdom?” If you’re navigating midlife, or preparing for it, this episode offers a powerful new way to understand this stage of life. Watch the episode to see how midlife can become a turning point, not a breakdown. Timestamps: 00:00 Welcome to Wisdom Wednesday 00:30 When Organizations Go Through Midlife 03:17 Change Management vs. Transition Management 05:00 Hormones and Andropause in Men 07:38 Career and Financial Disappointment 08:22 Growing Irrelevance in Midlife 09:20 Male Loneliness and Social Disconnection 10:06 Loss of Purpose After Career Changes 10:47 Low Testosterone and Men’s Health 13:55 Self-Esteem and Midlife Relationships 15:17 The Pain of Becoming Irrelevant 17:23 Menopause and Hormonal Changes for Women 19:34 The Pressure of Conventional Beauty 20:38 Invisibility in Dating and Work 22:04 Financial Challenges for Women 22:55 The Burden of Endless Caregiving 23:34 Hormone Replacement Therapy Debate 26:37 Communication in Relationships 27:19 Final Advice for Navigating Midlife Learn more about MEA at ⁠https://www.meawisdom.com/ #midlifecrisis #midlifetransition #midlifechanges #menvswomen #midlifepsychology #perimenopause #menopause #andropause #midlifeloneliness #midlifepurpose #agingandpurpose #modernelderacademy #chipconley #midlifeidentity #midlifeawakening

    26 min
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5
out of 5
57 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
    93
  • Rating
    Clean
  • Copyright
    © Chip Conley
  • Show Website
    The Midlife Chrysalis

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