The Midlife Chrysalis

Chip Conley
  • 5.0 (56)
  • 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. 5H AGO

    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

  2. 2D AGO

    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

  3. 4D AGO

    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

  4. 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

  5. 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

  6. MAR 23

    Why Love Requires Skills Most People Never Learn | Terry Real

    Why do so many relationships lose intimacy over time, even when love is still there? In this episode of Midlife Chrysalis, Chip Conley talks with renowned couples therapist Terry Real, creator of Relational Life Therapy and bestselling author of Fierce Intimacy and The New Rules of Marriage. For decades, Terry has helped couples understand why connection fades—and how to rebuild it. In this conversation, he explains: Why love requires skills most people were never taughtHow childhood patterns quietly shape adult relationshipsWhy traditional masculinity often blocks emotional intimacyHow couples can reignite connection in midlife Terry argues that relationships don’t fail because people stop caring, they fail because no one teaches us how to do intimacy well. Watch the episode to learn the relationship skills that can change everything. Timestamps: 01:30 Terry Real joins from Anguilla 03:01 What is Relational Life Therapy (RLT) 03:54 Why RLT takes sides in couples therapy 06:18 The core principles of RLT 08:14 Trauma triggers and childhood patterns in relationships 11:59 What holds men back in relationships 15:04 Redefining masculinity for intimacy 16:25 Patriarchy and the modern relationship crisis 18:23 Relational joy vs gratification culture 22:44 Reigniting intimacy as empty nesters 27:03 Why couples must confront resentment 29:46 Independence vs connection in long-term relationships 33:24 Are you really happy in your relationship 36:53 Why relationships require practice and skill 40:08 Wisdom bumper sticker Learn more about MEA at ⁠https://www.meawisdom.com/ #midliferelationships #relationshipadvice #intimacy #modernrelationships #couplestherapy #loveskills #relationshipskills #midlifechrysalis #emotionalintimacy #terryreal #relationshipgrowth #relationshipproblems #communicationinrelationships #longtermrelationships #midlifelove

    48 min

  7. MAR 20

    Pete Holmes on Psychedelics, God & Finding Meaning in Midlife

    The moment that breaks your life can also be the moment that transforms it. In this episode of Midlife Chrysalis, Chip Conley sits down with comedian and writer Pete Holmes for a deep and surprisingly funny conversation about heartbreak, spirituality, and the search for meaning. Pete shares how a painful divorce in his twenties pushed him to fully commit to comedy and set him on a journey into consciousness, psychedelics, fatherhood, and what it really means to live a good life. In this episode, Pete reveals: How his divorce became the turning point that changed his life and careerWhy humor may be one of the most powerful tools for healingWhat psychedelics taught him about consciousness and awarenessWhy midlife can actually be the most meaningful chapter of lifeThe life-changing idea: don’t believe everything you think Warm, honest, and thought-provoking, this conversation explores how laughter and self-awareness can transform even life’s hardest moments. 👉 Watch the full episode to hear Pete Holmes’ story and discover why humor might be the secret to a better life. Timestamps: 03:46 Is Pete Christian Comedian? 06:25 Was Jesus Funny? 09:04 Humor Humility and Getting Older 10:44 Can You Train Your Sense of Humor? 13:41 Why Midlife Is Actually Better 15:36 Fatherhood and Life in His 40s 19:52 Turning 47 and the Happiness Curve 20:59 Divorce at 28 and the Turning Point 26:17 Why Comedy Exploded After 9/11 30:42 Humor as Healing for Pain 31:54 Comedy Is Saying What Everyone Thinks 35:46 Aging What Gets Worse and What Gets Better 39:50 Psychedelics and Spiritual Awakening 46:39 Bringing Spirituality Into Comedy 49:48 Pete Holmes’ Best Life Advice 54:33 Relationship Advice That Actually Works 56:19 Final Thoughts and Richard Rohr Learn more about MEA at ⁠https://www.meawisdom.com/ #PeteHolmes #MidlifeChrysalis #MidlifeWisdom #ComedyPodcast #PeteHolmesInterview #StandUpComedy #SpiritualityAndComedy #MidlifeGrowth #PersonalGrowthPodcast #PsychedelicInsights #RichardRohr #LifeLessonsPodcast #ConsciousComedy #SpiritualAwakening #SelfDiscovery

    1h 2m

  8. MAR 18

    Midlife Pit Stop: Refuel Before the Next Chapter

    What if the most powerful move you could make at midlife… is to pause? In this episode of Wisdom Wednesday, Derek sits down with Chip Conley to explore the rise of the midlife sabbatical and why more people over 50 are choosing a reset instead of racing toward retirement. Chip challenges the old “learn, earn, retire” model and introduces a new idea: the midlife pit stop — a courageous break to refuel before the next chapter. In this conversation, you’ll learn: Why a sabbatical isn’t a vacation. It’s renewalHow stepping away can strengthen your career and relationshipsWhat Chip discovered during his own two-year breakHow to design a meaningful month off, even if a year feels impossible Midlife isn’t about slowing down. It’s about getting intentional. If this resonates, share it with someone who might need a reset and subscribe for more Wisdom Wednesday insights. Timestamps: 00:05 Spring Travel Chat & Baja Living 05:34 The Rise of the Midlife Gap Year 11:20 The Midlife Atrium Concept 13:15 Why Employers Should Support Sabbaticals 17:14 Starting Small with a Gap Weekend 18:07 Chip’s Two-Year Sabbatical Experience 23:13 Ego, Curiosity, and Deepened Friendships 24:31 How to Design a One-Month Sabbatical 26:58 Saving for a Midlife Pit Stop 29:19 Escaping One-Dimensional Living Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeReset #MidlifeSabbatical #MidlifeGapYear #SecondAct #LifeAfter50 #CareerBreak #SabbaticalLife #WorkLifeBalance #RetirementRedefined #PersonalGrowthJourney #EmptyNestLife #ReinventYourLife #MidlifeTransformation #PurposeAfter50 #ChipConley

    26 min
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Trailer

5
out of 5
56 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
    90
  • Rating
    Clean
  • Copyright
    © Chip Conley
  • Show Website
    The Midlife Chrysalis

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