The Midlife Chrysalis

Most people don’t realize they’re living someone else’s life until it’s too late. In this episode, Chip Conley sits down with Bonnie Wan, a renowned brand strategist and author of The Life Brief, who has spent decades studying human behavior, and now helps people redesign their lives with clarity and intention. Through her “Life Brief” method, people learn how to cut through the noise and make decisions that truly align with them. Key insights: Why clarity alone doesn’t change your lifeThe one question that reveals what you really wantHow to stop living on autopilotWhat’s really behind feeling stuck in midlife If something feels off but you can’t explain why, this will make it clear. Watch now and start taking your life back. Timestamps: (00:00) Intro and episode setup(04:04) Bonnie Wan introduction (04:44) Early life and path into advertising (07:47) The “Got Milk” story and key insight (13:05) What is The Life Brief (14:46) Clarity and “F**k Yes” feeling (16:24) Why people feel stuck in midlife (17:10) Powerful questions to change your life (20:00) Marriage crisis and breakthrough (23:06) “Take Our Time” life brief (26:15) From career to calling (30:01) Ambition from the inside out (31:38) What gets better with age (33:09) What does “enough” really mean (35:43) Redefining wealth as relationships (36:11) Designing a slower, intentional life (40:25) “Chase your goosebumps” advice (41:56) Breaking free from the success script (47:40) Final reflections and closing Learn more about MEA at ⁠https://www.meawisdom.com/ #LifeBrief #BonnieWan #FindYourFuckYes #MidlifeClarity #LifeOnPurpose #StopLivingSomeoneElsesLife #LifeRedesign #ClarityInLife #MidlifeAwakening #IntentionalLiving #LifeStrategy #PersonalClarity #ReclaimYourLife #InnerKnowing #LifeReset

You don’t stay relevant by knowing more. You stay relevant by staying curious. In this episode of Wisdom Wednesday, Chip Conley joins Derek Gehl to break down why curiosity, not experience or intelligence, is the real edge in midlife and beyond. Here’s what stands out: Curiosity is the antidote to irrelevanceAsking better questions beats having the right answersMidlife requires a shift from knowledge to wisdomLearning for no reason can unlock new purposeStaying curious keeps your mind sharp and engaged It’s a simple shift, but it changes everything. 👉 Watch now and start thinking like a beginner again Timestamps: 00:00 Why curiosity improves work and life 03:34 Curiosity as antidote to irrelevance 06:18 Chip’s experience at Airbnb 10:10 Power of asking better questions 12:33 Curiosity vs learning explained 14:46 Curiosity and innovation culture 18:04 Learning for curiosity not productivity 18:48 Turning curiosity into new paths 22:45 How curiosity looks for everyday people 25:51 Learning for the sake of passion 26:56 Lifelong learning and aging 28:38 Curiosity and brain health 29:07 Key question what are you a beginner in 30:12 Creating space for curiosity Learn more about MEA at ⁠https://www.meawisdom.com/ #curiosity #growthmindset #lifelonglearning #midlifegrowth #selfimprovement #personaldevelopment #mentalfitness #stayrelevant #learnhowtolearn #askbetterquestions #mindsetshift #reinventyourself #emotionalintelligence #careertransition #wisdom

Midlife might be the moment everything finally starts to make sense. In this episode of The Midlife Chrysalis, Chip sits down with branding expert Robin Fisher Roffer, who spent over 30 years shaping major brands, to explore how those same principles can help you reinvent your life. Robin shares her own powerful transition, stepping away from a successful career to start a whole new chapter, and what she’s learned along the way. In this episode, you’ll discover: Why real change starts by reconnecting with your original storyThe 3 essentials of a strong personal identity: clarity, consistency, and authenticityHow to define your own “tagline” for your next chapterA refreshing way to see midlife as freedom, finally If you’re feeling ready for something new, or just a little more you, this one will stay with you. 👉 Watch now and take the first step toward your next chapter. Timestamps: 03:44 Father’s influence and childhood story 06:55 Early exposure to advertising 08:12 Career path and starting agency 09:56 Brand strategy principles explained 13:34 Intuition and big ideas in branding 16:34 Applying branding to personal identity 18:33 Workshop transformations and examples 20:04 Fast decision-making and creativity 21:59 Rebranding midlife discussion 24:50 Taglines and brand positioning 27:28 Personal midlife transformation 32:26 Moving to Santa Fe and lifestyle 34:48 Wisdom bumper sticker 39:21 Workshop experience and benefits Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeReinvention #RebrandYourLife #StartOverAt60 #LifeAfter50 #PersonalBranding #FindYourPurpose #CareerChange #NextChapter #SelfReinvention #WomenOver50 #LifeTransformation #PersonalGrowth #SecondAct #MeaningfulLife #MidlifeChrysalis

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

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

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

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 

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

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

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

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

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

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

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

Most of us try to solve midlife. What if that’s exactly the wrong approach? In this episode, Chip Conley sits down with Bill Burnett and Dave Evans, the minds behind Designing Your Life, to rethink one of the most misunderstood seasons of adulthood. Drawing from design thinking, human curiosity, and decades of real-world experimentation, they offer a refreshing alternative to the pressure of “figuring it all out.” Instead of chasing the right answer, Bill and Dave invite us to prototype our way forward gently, curiously, and without fear of getting it wrong. Key insights from the conversation: Midlife isn’t a crisis. It’s a chrysalis, a space for becomingThere is no single “right” life, only many good lives you can designStop solving your life and start prototyping small experimentsCuriosity matters more than certaintyMeaning isn’t found in big answers, but in everyday moments of flow This is a hopeful, grounding conversation for anyone who feels stuck, restless, or quietly ready for what’s next. 👉 Click to watch and discover how to design the next chapter of your life without pressure, panic, or pretending. Timestamps: 03:48 What Designing Your Life is 06:55 What is design thinking 09:22 Designing yourself as a wicked problem 10:20 Gravity problems and anchor problems 12:32 Opening the aperture of choice 14:03 Applying design thinking to midlife 16:49 Creativity and reinvention after success 18:03 Are midlifers more stuck than younger people 19:14 Permission to change in midlife 21:50 Prototyping your next chapter 24:08 Self-criticism fear and resistance 25:00 Learning to be incompetent again 27:49 Personal midlife transitions 31:14 Dark night of the soul 36:53 Introducing the meaning book 38:11 Designing meaning in everyday life 40:21 Redesigning midlife as a culture 44:01 Rethinking work and education 48:25 Reframing midlife identity 52:07 Wisdom bumper stickers Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeChrysalis #DesignYourLife #MidlifeTransition #FindingPurpose #SecondHalfOfLife #LifeDesign #MidlifeMeaning #PersonalGrowth #MidlifeReinvention #DesignThinking #CareerTransition #CuriosityMindset #ModernElder #MidlifeWisdom #LifeAfter40

Real growth rarely happens when life feels comfortable. It begins when we slow down, question our patterns, and face the deeper truths about how we live and lead. In this episode of Midlife Chrysalis, Chip Conley talks with Diana Chapman, leadership coach and co-author of The 15 Commitments of Conscious Leadership. Drawing from decades of coaching founders and CEOs, Diana shares practical wisdom on how awareness can transform relationships, leadership, and personal growth. In this conversation, she explores: How the Drama Triangle fuels conflict and how to step out of itWhy playfulness is essential in long-term relationshipsThe difference between your zone of excellence and your zone of geniusWhy midlife transformation often requires quiet and surrender The episode also turns deeply personal as Chip reflects on mortality, purpose, and stepping away from constant busyness to reconnect with what matters most. Watch the full episode to explore what a true midlife chrysalis can look like. Timestamps: 03:43 Diana’s path to conscious leadership 07:37 Teach the Class tool 09:03 The Drama Triangle explained 10:43 Personas and playful awareness in relationships 12:31 Lessons from a 44-year marriage 14:32 The 15 Commitments of Conscious Leadership 16:55 Conscious leadership in today’s polarized world 17:53 The new book No Drama Teams 22:05 Trust vs threat in team dynamics 24:26 Coaching leaders through crisis 27:53 What makes a great coach 33:10 Discovering your zone of genius 36:28 Diana’s midlife chrysalis experience 39:42 Chip’s idea for a “month of dying” retreat 44:20 Lessons from a founder facing death 46:04 The value of fallow ground and quiet time 47:18 Designing a life of aliveness 48:36 Wisdom vs knowledge in the age of AI 49:26 Diana’s wisdom bumper sticker 50:21 Childhood truth and trusting your inner knowing 52:30 Reflections on truth, growth, and love 55:17 Closing reflections and invitation to the workshop Learn more about MEA at ⁠https://www.meawisdom.com/ #DianaChapman #ConsciousLeadership #15CommitmentsOfConsciousLeadership #DramaTriangle #ConsciousLeadershipGroup #ZoneOfGenius #LeadershipCoaching #ConsciousLeadershipTools #NoDramaTeams #LeadershipMindset #EmotionalIntelligence #SelfLeadership #LeadershipTransformation #ConsciousLiving #MidlifeChrysalis

The drive that made you successful may not be meant to lead you forever. In this Wisdom Wednesday episode of The Midlife Chrysalis, Chip Conley and Derek Gehl explore the shift from ego to soul, the defining transition of the second half of life. Drawing from his personal journey, his role as a “modern elder” at Airbnb, and insights from Richard Rohr and Connie Zweig, Chip reflects on what happens when achievement stops being enough. In this conversation, you’ll learn: Why ego builds the first half of life but can limit the secondHow to move from performer to elderWhat generativity really meansWhy awe and space are essential for soul growth If you’ve felt a quiet nudge that there’s something deeper beyond success, this episode will resonate. Tune in and consider who’s driving your life now. Timestamps: 01:13 Gehl’s Proud Dad Moment 04:17 Enneagram and Early Identity 06:20 Coming Out and Authenticity 09:40 The Ballroom Dance Metaphor 11:47 Richard Rohr and Falling Upward 14:14 Living Stuck in Ego 15:24 Ego, Generativity, and Aging 18:22 From Frontman to Guide 19:30 Reincarnation & Evolving Conciousness 21:32 Where People Get Stuck 25:07 Spirituality & Seeking Awe 26:06 Practices to Soften the Ego 27:26 Richard Rohr Workshop in Santa Fe Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeCrisis #MidlifeTransformation #FindingPurpose #LifeAfter50 #PersonalGrowth #SpiritualGrowth #SelfDiscovery #IdentityShift #PurposeDrivenLife #EgoVsSoul #SecondHalfOfLife #MeaningInLife #InnerGrowth #ModernElder #MidlifeAwakening

What if the real key to longevity isn’t a biohack but a wake-up call? In this episode, Dr. Brad Jacobs, longevity expert, integrative medicine pioneer, and former UCSF professor, shares what truly helps us thrive in midlife. After losing his father to cancer at 27, Brad made it his life’s work to understand how we can live longer and better. In this episode, we explore: What actually extends your life (and what’s a distraction)Why sleep and stress matter more than most supplementsHow psychedelics are reshaping emotional healingWhat modern masculinity has to do with longevityWhy midlife is a powerful reset, not a decline If you’re in your second half and ready to live with more vitality, clarity, and purpose, this conversation will challenge and inspire you. Press play! Your midlife upgrade starts here. Timestamps: 04:10 Martial arts to longevity medicine 08:58 Rethinking US healthcare 11:26 Integrative health in midlife 14:42 Sleep optimization and wearables 18:02 Longevity myths and overtraining 19:13 Food philosophy and Blue Zones 21:59 Stress overload and chronic disease 25:50 Love, partnership and second chances 29:57 Psychedelic medicine and ketamine 35:11 Ketamine vs. Psilocybin 37:45 Modern masculinity redefined 41:08 Chip on coming out & courage 48:50 Live Longer Age Better workshop 50:28 Wisdom Bumper Sticker Learn more about MEA at ⁠https://www.meawisdom.com/ #Longevity #MidlifeHealth #HealthyAging #IntegrativeMedicine #LiveLonger #PsychedelicTherapy #KetamineTherapy #ModernMasculinity #MidlifeReset #SleepOptimization #BlueZones #EmotionalHealth #Biohacking #PreventChronicDisease #MidlifeTransformation

In this episode of Midlife Chrysalis, poet and philosopher David Whyte explores why midlife often feels like losing your way and why that experience may be exactly what opens the door to deeper meaning. Drawing on poetry, psychology, and Dante’s famous “dark wood,” David explains how moments of uncertainty can become powerful turning points in our lives. In this conversation, he shares: Why midlife can feel like exile from your old lifeWhat Dante’s “dark wood” teaches about transformationWhy silence and the unknown are essential for growthHow vulnerability and grief can lead to wisdom If you’ve ever felt lost, stuck, or questioning the direction of your life, this conversation offers a powerful new way to see it. 👉 Watch the full episode and discover why getting lost in midlife might be the beginning of something greater. Timestamps: 02:29 What “Midlife Chrysalis” Really Means 06:37 Dante and the Exile of Midlife 13:00 Aging, Eldership and the Inner Horizon 17:40 The Power of Silence and Contemplation 22:55 Poetry, Discipline and Inner Transformation 27:01 Why People Turn to Poetry in Midlife 33:13 Masculinity, Friendship, and Emotional Isolation 37:39 Work as a Spiritual Pilgrimage 44:22 The First Step to Deeper Conversations 50:00 Friendship with the Unknown 52:30 Vulnerability, Care, and Asking for Help 55:09 Wisdom Learned Between 50 and 70 58:27 Final Reflections on Caring and Presence Learn more about MEA at ⁠https://www.meawisdom.com/ #midlifecrisis #midlifetransformation #midlifeawakening #midlifejourney #personalgrowth #selfdiscovery #lifeafter40 #lifeafter50 #purposeinlife #innertransformation #philosophyoflife #poetryandwisdom #dantesinferno #spiritualgrowth #meaningoflife

Midlife isn’t about adding more. It’s about letting go. In this Wisdom Wednesday episode of The Midlife Chrysalis, Chip Conley joins Derek Gehl to explore The Great Midlife Edit, the courage to release what has quietly run its course. Drawing from his near-death experience and the sale of his company, Chip shares what it really means to “empty your cup” and create space for what’s next. In this conversation, you’ll learn: Why midlife shifts us from accumulation to editingHow to recognize what’s ready to “graduate” from your lifeThe three stages of transition — endings, the messy middle, and new beginningsA powerful question to help you begin your own edit If something in your life feels heavy, outdated, or complete, this episode is your gentle invitation to let go and begin again. Listen in, reflect, and share it with someone ready for their next chapter. Timestamps: 00:00 Welcome to Wisdom Wednesday 00:18 Heated Rivalry and Mark Carney 03:29 The Great Midlife Edit 07:10 Empty Your Cup Japanese Story 10:15 Transitional Intelligence and Endings 11:46 Surrender and the Serenity Prayer 15:15 Chip’s Major Life Edits 18:45 Gut Check Practice 20:22 Editing Family Relationships 22:29 Question to Begin Your Own Edit 24:10 Ritualizing Letting Go Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeChrysalis #MidlifeTransition #MidlifeReset #LettingGo #LifeTransitions #SecondAct #PersonalGrowth #Reinvention #EmptyYourCup #TransitionalIntelligence #PurposeInMidlife #LifeAfter50 #EmotionalWellbeing #SabbaticalLife #ChipConley

What happens when the world sees a champion… but you’re still figuring out who you are? In this episode of The Midlife Chrysalis, Olympic legend Greg Louganis opens up about the life behind the gold medals and the deeper journey beyond fame. From childhood wounds and public adoration to living with HIV and facing mortality at 28, Greg shares how his identity has evolved over decades. You’ll hear: • How early trauma shaped his drive to perform • Why love, not medals, fueled his career • What midlife taught him about letting go of personas • How meditation, shadow work, and silence helped him heal This is a conversation about reinvention, mortality, and becoming whole, not despite your past, but because of it. If you’re navigating midlife, identity shifts, or personal healing, this episode will speak to you. 👉Press play and enter the chrysalis. Timestamps: 02:50 Welcome to Midlife Chrysalis 03:13 Moving to Panama and new chapter 04:50 First trauma and feeling abandoned 11:20 Performing and early competition 16:01 Olympic journey and first medals 17:14 Fame and public attention 20:40 Coach Ron O’Brien and motivation 24:55 Identity, HIV, and sponsorship struggles 29:28 Living with public persona 33:29 Evolving identity and being content 36:37 Meditation yoga and inner work 42:11 Looking inward for answers 44:39 Life wisdom and 45-year relationship 49:22 Mortality, HIV, and acceptance of death Learn more about MEA at ⁠https://www.meawisdom.com/ #GregLouganis #MidlifeChrysalis #OlympicLegend #HIVAwareness #MidlifeTransformation #PersonalGrowthJourney #IdentityShift #HealingJourney #ShadowWork #MeditationPractice #FacingMortality #Reinvention #LGBTQVoices #ResilienceStory #FromFameToFreedom

Midlife can feel unsettling even when life looks successful on paper. This episode explores why that discomfort appears and how it can become a source of clarity rather than crisis.  Our guest is Kieran Setiya, MIT philosophy professor and author of Midlife: A Philosophical Guide. Drawing from philosophy and lived experience, he offers a calm, deeply human way of understanding regret, time, ambition, and meaning in the middle years of life.  In this conversation, you will learn: Why midlife is shaped by the past we cannot undo and a future that feels shorterHow goal chasing can quietly drain meaning from everyday lifeThe difference between living for outcomes and living through meaningful processesWhy regret and existential FOMO are signs of a rich value system, not personal failureHow attention, attachment, and acceptance create a more grounded way to live This episode is thoughtful, reassuring, and deeply practical for anyone questioning direction, purpose, or satisfaction in midlife. Listen now and discover a wiser, steadier way to meet the second half of life.  Timestamps: 02:59 Early interest in philosophy 05:28 Philosophy and physics connection 07:03 Why write about midlife 10:15 What defines midlife 12:46 Pressures, regret, and time poverty 15:27 Telic and atelic activities 20:03 Intrinsic and extrinsic motivation 21:23 Flow and engagement 22:37 Finding atelic activities 25:24 Chronos and Kairos 30:00 Anticipated regret as wisdom 34:48 Choosing a personal philosophy 37:38 Philosophers Kieran admires 40:47 When midlife ends 43:42 Philosophy and young people 48:19 Philosopher as president 51:03 Making philosophy practical 53:26 A life philosophy bumper sticker 57:37 Attachment and responsibility  Learn more about MEA at ⁠https://www.meawisdom.com/  #kieransetiya #midlifephilosophy #telicvsatelic #midlifereckoning #existentialregret #meaningoverachievement #philosophyofmidlife #timeandmeaning #midlifereflection #existentialfomo #processovergoals #lifewithoutburnout #modernelderacademy #attentionandmeaning #livingwellmidlife

What happens when time stops feeling endless and starts feeling real? In this episode of Wisdom Wednesday, Chip Conley shares how living with cancer reshaped his relationship with time, purpose, and urgency in midlife. Joined by Derek Gehl, Chip reflects on cancer scans, mortality, and why remembering that life is finite can actually deepen meaning, not fear. Together they explore: Why memento mori can bring clarity, not darknessHow midlife urgency is about intention, not panicWhat legacy really means beyond achievement This is a warm, life-affirming conversation about choosing what matters most when you realize tomorrow isn’t guaranteed. 👉 Watch now, and join the conversation by leaving a comment or review. Timestamps: 00:00 Opening and setup 00:42 Episode introduction 01:00 Workshops and unexpected contrasts 03:12 Ricky Williams and walking away from football 04:28 Cancer scans and living with uncertainty 05:20 Death as a daily presence 06:00 Prostate cancer diagnosis and treatment journey 10:43 Hormone therapy and energy loss 13:46 Feeling mortality in the body 14:16 Memento mori and midlife urgency 16:30 Legacy and ripple of impact 18:24 Near death experience story 22:47 Succession planning and leadership wisdom 23:18 Talking about death without fear 26:10 Purpose usefulness and meaning 28:20 Wisdom bumper sticker on mortality 30:04 Gratitude and closing reflections Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeWisdom #CancerJourney #LivingWithUrgency #MementoMori #MidlifePurpose #FacingMortality #LifeAfterCancer #ModernElder #MeaningfulLife #LegacyAndPurpose #MidlifeReflection #WisdomWednesday #PersonalGrowth #LifePerspective #ChipConley

In this candid and heartfelt conversation, Airbnb co-founder and CEO Brian Chesky joins Chip Conley to explore the hidden side of success. From imposter syndrome to the emotional aftermath of the IPO, Brian shares what midlife has taught him about ambition, belonging, and finally realizing he is enough. In this episode, you’ll hear:• Why success didn’t fix his loneliness• How leadership evolved from control to connection• The wake-up call that followed Airbnb’s $100B milestone• Why midlife is a chance to redefine what truly matters This is a conversation about growth, vulnerability, and choosing relationships over relentless achievement.If you’re navigating success, questioning your next chapter, or redefining what fulfillment means, this one’s for you.Listen in and reflect on what “enough” means in your life. Timestamps:00:00 Reunion and reflecting on 13 years since Airbnb began01:02 How Brian recruited Chip and the early Airbnb vision02:27 Chutzpah and learning from mentors04:00 Discovering hospitality as Airbnb’s true business06:43 Early partnership dynamics and mutual mentorship11:21 Advice to his 26 year old founder self12:20 Imposter syndrome and leadership growth15:42 From creative outsider to Fortune 500 CEO17:26 Childhood, not belonging and ambition22:48 Loneliness after success and the IPO realization27:54 Investing in friendships and rebuilding connection29:00 Founder mode and evolving leadership style37:24 Redefining success in midlife38:17 Hoffman process and realizing he is enough41:35 Fear of intimacy and unfinished business50:03 The Airbnb Open and scaling with soul54:20 Wisdom bumper stickers and life lessons56:04 In you lies unknown potential1:00:48 I am enough and always was Learn more about MEA at ⁠https://www.meawisdom.com/

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

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

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

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

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/

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/

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/

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/

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/

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/

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/

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/ 

Midlife isn’t the end of the story, it’s the chapter where something new wants to begin.In this episode of Midlife Chrysalis, Chip Conley sits down with Pam McLean, pioneering coach, co-founder of the Hudson Institute of Coaching, and a guiding voice on adult development and the “bonus years.” Together, they explore why midlife isn’t about stepping back, but about letting go and moving forward with intention. Pam shares: Why releasing old identities is essential for growthWhat the “bonus years” make possible at any ageHow Life Forward helps reframe change as opportunityWhy discomfort, grief, and curiosity are part of becomingWhat truly makes a great coach — in life and in leadershipThis is a warm, thoughtful conversation for anyone standing at a crossroads and wondering what comes next. Watch now and discover how midlife can become a powerful new beginning.  Timestamps: 03:32 Pam’s early life and background 04:17 From clinical psychology to coaching 07:06 How coaching has developed 09:31 Life Forward and Hudson Institute 11:46 The midlife happiness curve 14:53 Cancer as a life teacher16:06 Hudson Institute and MEA connection 18:08 Letting go of old identities 21:50 Navigating major life transitions 26:27 Why experimentation matters 27:39 Men vs women in midlife 31:01 What makes a great coach 33:47 Why people choose coaching 35:15 Gender balance in coaching35:51 Coaching in the age of AI 38:20 How to choose the right coach 40:38 Creativity later in life 42:41 Wisdom bumper sticker  Learn more about MEA at ⁠https://www.meawisdom.com/

Midlife isn’t falling apart. It’s asking for your attention. In this episode of Midlife Chrysalis, Chip Conley dismantles the idea of the “midlife crisis” and replaces it with a far more hopeful and powerful framework: midlife as a chrysalis, a necessary transition into a second adulthood. Drawing from social science, psychology, and his own deeply personal story, Chip explains why midlife often feels like a breakdown, why it’s actually normal, and how it can become the most meaningful chapter of your life. In this conversation, you’ll discover: - Why happiness dips in midlife and rises afterward - How identity loss and burnout are signals, not failures - Why midlife hits men and women differently - How wisdom and purpose often peak later in life If you’re feeling burned out, disoriented, or quietly wondering, “Is this all there is?”, the answer, as Chip shows, is no. This is where something new begins. 👉 Watch now to understand what midlife is really asking of you and how to move from breakdown to transformation. Timestamps: 01:20 The Origin of the Midlife Crisis Idea 04:40 The U Curve of Happiness 06:21 Why Midlife Is Not a Crisis 09:12 Becoming a Modern Elder 11:24 Chip’s Midlife Struggles 21:11 Why Midlife Lacks Support Systems 23:17 Biology vs Life Circumstances 25:49 How to Move from Crisis to Chrysalis 30:23 Watching People Self-Destruct in Midlife 34:18 Rebranding Midlife for the Future Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeCrisis #MidlifeTransformation #SecondAdulthood #MidlifeWisdom #MidlifePurpose #ModernElder #MidlifeBurnout #HappinessCurve #LifeTransitions #MidlifePodcast #AgingWell #PersonalGrowth #MidlifeReset #LifeAfter40 #FindingPurpose

What happens when ambition slows down, and wisdom begins to lead? Chip Conley, founder of Modern Elder Academy and host of Midlife Chrysalis, sits down with California Governor Gavin Newsom for a rare, deeply personal conversation shaped by nearly 30 years of mentorship and friendship. This is not a political interview, it’s an honest exploration of midlife, identity, and becoming.Together, they reflect on: How Gavin’s upbringing and dyslexia shaped his leadershipWhy legalizing same-sex marriage became a defining moral momentWhat the “winter years” between mayor and governor revealedHow fatherhood and midlife reshaped his relationship with powerWhy grace, humility, and resilience matter now more than everWarm, thoughtful, and deeply human, this episode explores what’s possible when we slow down and listen. If you’re navigating change or reinvention, watch now and step into the chrysalis. Timestamps: 03:26 Welcome to Midlife Chrysalis 04:06 Long friendship and early mentorship 05:54 Childhood and family background 08:48 Gavin’s writing experience 16:03 Becoming mayor of San Francisco 17:38 Decision to legalize gay marriage 25:11 Impact of marriage equality 27:54 Political winter as lieutenant governor 29:24 Identity loss and slowing down33:21 Humility and leadership lessons 35:22 Grace humility after years of division 38:46 The lost art of civil disagreement41:49 Political vision and building bridges 44:10 Stoicism and wisdom traditions 47:44 Fatherhood and authenticity 49:27 Wisdom bumper stickerLearn more about MEA at ⁠https://www.meawisdom.com/

What happens when success stops working and midlife hits hard? Blake Mycoskie, founder of TOMS Shoes, shares the story behind his most difficult chapter. After building a global brand and achieving massive success, Blake found himself facing a deep midlife reckoning marked by depression, loss of identity, and an urgent search for meaning beyond achievement. Blake opens up about: - How selling part of TOMS triggered an unexpected identity collapse - Why midlife depression often follows success, not failure - The treatments and inner work that helped him recover, including ketamine therapy and TMS - The simple but life-changing realization that shifted everything: “I am enough” - Why connection and community matter more than success or status 👉 Watch now to hear Blake Mycoskie’s most vulnerable and meaningful story yet. Timestamps: 01:11 Blake’s early entrepreneur journey 02:49 Reality Central and first major failure 04:59 The business lesson that shaped TOMS 07:49 Creating the one for one model 08:43 Selling TOMS and losing identity 12:36 Depression behind the public image 16:23 Searching for relief outside himself 17:24 Medication fog and deep isolation 19:30 Why telling others saved his life 20:54 Moving beyond traditional medication 21:12 Ketamine and TMS 25:53 Discovering the core wound 28:49 India and lasting inner freedom 33:27 Launching the Enough initiative 35:58 I’m Enough ritual poem 37:57 How the nonprofit model works 38:47 The growing mental health crisis 43:13 Self compassion and flow state 46:28 How to support someone in depression 51:54 Living with fear of relapse 54:17 Wisdom bumper sticker Learn more about MEA at ⁠https://www.meawisdom.com/ #BlakeMycoskie #MidlifeCrisis #MentalHealthAwareness #EntrepreneurMentalHealth #SuccessAndDepression #TOMSFounder #MidlifeJourney #DepressionRecovery #FindingPurpose #SelfWorth #MentalHealthPodcast #MidlifeTransformation #HealingJourney #MenAndMentalHealth #IAmEnough

What if aging alone isn’t the only option? As midlife reshapes relationships, identity, and housing, a bold question emerges: what if women chose community instead of solitude? In this Wisdom Wednesday episode, Chip Conley, founder of Modern Elder Academy, joins Derek Gehl to explore the early-stage idea behind Golden Girls–style living, an intentional housing experiment he’s beginning in Santa Fe to address loneliness, gray divorce, and the realities of solo aging. In this episode, you’ll learn: - Why more women are aging solo in midlife - Why social connection matters more than health hacks - How housing no longer fits modern midlife needs - What Golden Girls–style living could look like in practice This isn’t a finished solution — it’s a timely experiment that reimagines how we live and age. 👉 Watch now and decide if community belongs in your next chapter. Timestamps: 02:40 Golden Girls homes concept 03:41 Gray divorce and solo agers 06:20 Loneliness and housing mismatch 08:05 Why Golden Girls homes now 10:10 The Santa Fe pilot homes 12:49 Workshops and community vision 15:29 What the research revealed 18:14 Matching roommates and house culture 21:10 Affordability and rental model 24:10 What about men 26:36 Long term vision and legacy 29:21 How to get involved 29:55 Final reflections Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeChrysalis #GoldenGirlsHomes #MidlifeTransition #SoloAgers #GrayDivorce #LonelinessEpidemic #IntentionalLiving #MidlifeCommunity #WomenOver50 #AgingWell #CommunityLiving #ModernElders #MidlifeWisdom #HousingInnovation #SocialConnection

Aging in America has never been the same for everyone. Chip Conley sits down with Ray Jetson, pastor, former Louisiana legislator, and author of Aging While Black, to explore why aging isn’t a race-neutral experience and what it really means to age well in a system that was never built for everyone.Ray shares a simple, powerful way to rethink aging through community, innovation, and shared wisdom across generations. In this episode, you’ll learn: Why aging while Black carries unique structural and economic realitiesHow the village concept and Sankofa help bridge past, present, and futureWhy technology and mutual mentorship matter for aging wellWhat collective longevity looks like across generationsThis conversation invites us to rethink aging, equity, and how we care for one another at every stage of life. Watch now and join the conversation.  Timestamps: 03:02 Three pillars of aging while black 05:43 The village concept and African origins 08:18 Ubuntu and community identity 11:11 The Black church as a village 13:07 Embracing innovation and technology 18:39 Sankofa and learning from the past 24:38 Intergenerational circles and family wisdom 27:35 Collective longevity across generations 33:08 Keeping hopeful and building systems 39:50 Sources of inspiration and leadership 43:20 What makes aging while black different 51:03 Wisdom bumper sticker 53:27 Closing thoughts and workshop invitation  Learn more about MEA at ⁠https://www.meawisdom.com/

Most leaders are chasing short-term wins and missing the long game. In this episode, Chip Conley talks with Rand Stagen, founder of the Stagen Leadership Academy, about what’s quietly breaking leadership today and how to lead with purpose, perspective, and staying power. Rand shares hard-earned insights from decades of working with CEOs and entrepreneurs who want more than success, they want meaning. You’ll learn: - Why short-term thinking undermines great leadership - What it means to play the infinite game - How awareness creates better choices - Why the best leaders think in decades, not quarters If you’re leading others, or rethinking your own direction, this conversation offers a clear, grounded reframe. 👉 Watch now and start playing the long game. Timestamps: 05:51 Rand Stagen personal leadership journey 07:47 The advice for young entrepreneurs 10:17 Entrepreneurial roots and early influences 12:43 Founding the Leadership Academy 16:50 Structure of the leadership program 22:23 Integral theory explained 26:18 Leadership and polarization 35:57 Practical advice for leaders 41:45 Conscious Capitalism principles 45:41 Short term versus long term thinking 52:01 Workshop goals and takeaways 56:18 Who the workshop is for 58:12 Leadership wisdom and closing insight Learn more about MEA at ⁠https://www.meawisdom.com/ #LeadershipDevelopment, #ConsciousLeadership, #LongTermThinking, #LeadershipMindset, #PersonalGrowth, #ExecutiveLeadership, #PurposeDrivenLeadership, #InfiniteGame, #MidlifeLeadership, #SelfLeadership, #LeadershipPodcast, #AwarenessAndChoice, #ModernLeadership, #LeadershipWisdom, #ChipConley

Most companies are racing toward AI, efficiency, and scale while quietly losing the one advantage that actually sustains great leadership: wisdom. In this Wisdom Wednesday episode, we reveal why culture, lived experience, and human judgment matter more than ever. Chip draws on decades of leadership experience to explain why many organizations are losing their edge and what they can do to reclaim it. In this episode, you’ll learn: - Why leadership is a practice, not a personality trait - How culture is shaped when leaders aren’t in the room - What companies lose when institutional wisdom disappears - The difference between knowledge workers and wisdom workers in the AI era As technology accelerates, human skills become the real competitive edge. 👉 Watch now and discover how wisdom future-proofs leadership and culture. Timestamps: 00:13 Leadership as a practice 02:29 Culture leaders overlook 05:18 Defining real company culture 08:57 Institutional wisdom loss 13:47 Knowledge workers vs wisdom workers 18:30 AI impact on early careers 22:22 Humanities and philosophy comeback 22:44 Wisdom at Airbnb 25:53 Informal mentors and EQ 27:57 Leading yourself first 28:18 Resources and upcoming workshop 30:12 Closing thoughts Learn more about MEA at ⁠https://www.meawisdom.com/ #LeadershipWisdom #WisdomAtWork #FutureOfLeadership #AIAndLeadership #CompanyCulture #EmotionalIntelligence #KnowledgeVsWisdom #HumanSkills #MentorshipMatters #InstitutionalWisdom #LeadershipDevelopment #WisdomWednesday #LeadershipCulture #AIImpact #ModernLeadership

Have you ever reached a point in life where what once worked… suddenly doesn’t? In this warm conversation with Chip, Ben Katt, MEA’s faculty in residence and author of The Way Home, offers a hopeful reframe of midlife. Rather than seeing it as a breakdown, Ben invites us to see this season as a meaningful transition, one that asks us to let go of old roles and reconnect with who we truly are. In this episode, you’ll discover: - Why midlife often feels disorienting, even when life looks “successful” on the outside - How releasing familiar identities creates space for deeper purpose and wholeness - Why stillness, reflection, and meditation are essential during times of change - How community and support help us move through transitions with more easy If you’re feeling restless, uncertain, or quietly asking “What’s next?”, this conversation offers clarity, comfort, and a sense of direction. 👉 Watch now and explore what this chapter of your life is gently calling you toward. Timestamps:00:35 The Hero’s Journey and The Way Home 04:49 Ben’s five-year soul journey 07:20 Achievement perfectionism and people pleasing 09:44 Meditation and inner balance 13:19 Phase 1: Leaving the familiar 15:46 Phase 2: Falling into the unknown 18:30 Dark night of the ego 20:51 Wander in the wild 23:56 Support and community 29:52 Phase 3: Rising to wholeness 33:46 Stillness and begin again 38:58 Teaching wisdom without religion 44:13 The wisdom well metaphor 47:21 Why wisdom matters now 50:28 Wisdom bumper sticker Learn more about MEA at ⁠https://www.meawisdom.com/ Find Ben Katt at https://benkattofficial.com/ #MidlifeTransition #MidlifeCrisis #MidlifeTransformation #HeroJourney #FindingPurpose #MidlifeWisdom #LifeTransitions #PersonalGrowth #MidlifeAwakening #SecondHalfOfLife #InnerWork #MeaningInMidlife #JosephCampbell #WisdomTraditions #MidlifeChrysalis

What if the wellness advice you followed for years stops working after 50? In this episode, wellness pioneers Jeff Krasno, co-founder of Wanderlust, and Schuyler Grant, founder of Kula Yoga Project, share how their approach to health quietly but radically shifted in midlife, and why many popular wellness habits fall short as we age. With decades spent in yoga, wellness festivals, and lived experience, they share what actually matters now. They share insights on: - Why yoga alone isn’t enough after 50 - How muscle and strength shape metabolic and brain health - The importance of diverse movement, not extremes - How simple habits and presence support long-term well-being This is a grounded, honest conversation about aging well — without hype or shortcuts. 👉 Watch now and rethink what midlife wellness really requires. Timestamps: 01:22 Skylar’s yoga studio near Ground Zero 05:54 The origins of Wanderlust 09:47 Early resistance to the festival idea 11:28 Wellness hotels and business travel 14:32 Challenges of working with a spouse 20:52 What wellness means after 50 20:52 Muscle, metabolism, and aging 26:30 Yoga versus strength training 29:43 Muscle health and brain health 31:37 Diversity of movement in midlife 34:38 Curiosity, learning, and discomfort 37:34 Habit stacking explained 40:27 Wellness and politics 45:49 Upcoming Baja workshop 49:27 Wisdom bumper stickers Learn more about MEA at ⁠https://www.meawisdom.com/ #WellnessAfter50 #MidlifeWellness #HealthyAging #StrengthAfter50 #MuscleAfter50 #AgingWell #Over50Health #MidlifeHealth #LongevityLifestyle #FunctionalFitness #WellnessPodcast #HealthyMidlife #MindBodyHealth #HabitsForHealth #LifeAfter50

Why most New Year’s resolutions fail before February? In this episode of Wisdom Wednesday, we take an honest look at why good intentions fade quickly and share a simple, practical framework for building habits that last. Drawing from real-life experience, we break down how to turn good intentions into daily actions, without relying on motivation alone. In this episode, you’ll learn: - Why most resolutions fail - How habit stacking makes change automatic - The “Four Ps” that make goals stick - Why public accountability matters - How to build habits that last beyond January If you’re done repeating the same resolutions every year, this episode will help you do it differently. 👉 Watch now and start the year with habits that actually stick. Timestamps: 00:44 Morning people and Baja midnight 01:39 Why New Year’s resolutions fail 02:07 Common resolutions and lack of a plan 03:30 Habit stacking explained 05:10 Turning resolutions into daily practice 06:10 The four Ps framework 07:45 Pairing and social accountability 08:39 Passion versus accountability 09:50 Why fewer goals work better 11:03 Learning from past resolutions 11:50 Personal resolutions and alcohol 13:10 Family time as a long-term priority 14:14 Final reflections for 2025 15:02 Age, milestones, and perspective Learn more about MEA at ⁠https://www.meawisdom.com/ #NewYearsResolutions #HabitBuilding #HabitsThatStick #PersonalGrowth #MidlifeWisdom #BehaviorChange #GoalSetting #Accountability #HabitStacking #Mindfulness #SelfImprovement #Longevity #Wellbeing #LifeDesign #WisdomWednesday

Midlife can feel confusing, even when life looks good from the outside. Careers change, relationships shift, and the way we see ourselves starts to evolve, leaving many people feeling stuck in between what was and what’s next. In this episode, Kari Cardinale, Chief Content Officer and partner at Modern Elder Academy, explains why these moments aren’t breakdowns but transitions, and why learning to navigate them is an essential life skill. Through her work on Transitional Intelligence, Kari shares what’s really happening during midlife change and how to move through it with greater clarity and confidence. You’ll learn: • Why most midlife “crises” are actually misunderstood transitions • The three stages of change: endings, the messy middle, and new beginnings • Why the messy middle feels so hard — and why it matters • How rituals, community, and small “glimmers” guide what comes next If you’re feeling stuck or sensing a shift in your life, this episode will help you understand where you are and how to move forward. 👉 Navigating Transitions online course from Modern Elder Academy offers a supportive, step-by-step way to work through change with clarity and confidence, starting March 2: https://www.meawisdom.com/navigating-transitions-online/ Timestamps: 01:20 What is transitional intelligence 03:58 The three stages of transition 06:02 Voluntary and involuntary change 08:02 Why transitions take longer than we expect 11:50 The role of ritual in midlife 15:54 The messy middle and uncertainty 17:53 Glimmers and new beginnings 21:44 Growth mindset in midlife 24:28 Kari’s personal transition story 28:37 The birth of Modern Elder Academy 31:36 Love and relationships in midlife 34:48 What truly gets better with age 37:23 Building community and belonging 42:31 Wisdom bumper sticker Learn more about MEA at ⁠https://www.meawisdom.com/ #KariCardinale #MidlifeTransitions #MidlifeChange #MessyMiddle #LifeTransitions #PersonalGrowth #MidlifeWisdom #ModernElder #TransitionalIntelligence #EmotionalIntelligence #MidlifePurpose #NewBeginnings #GrowthMindset #MidlifeJourney #InnerWork

He didn’t plan on being successful. He just followed what pulled at him and kept letting go when it stopped working. In this episode, Stacy Peralta, legendary skateboarder, filmmaker behind Dogtown and Z-Boys, and modern elder, shares how a life built on passion, curiosity, and vulnerability led him from skateboarding to filmmaking to painting, without clinging to any single identity. Rather than chasing security or certainty, Stacy reveals why reinvention requires becoming a beginner again and why midlife may be the most powerful time to do it. In this conversation, Stacy explores: - Why holding onto past identities quietly blocks your future - How embracing vulnerability and being a “kook” unlocks growth - The difference between loving something and knowing when to let it go - How intuition, not logic, often guides the most meaningful transitions - Daily practices that keep creativity, curiosity, and vitality alive 👉 Watch the full episode now and discover why letting go might be the most powerful move you can make. Timestamps: 00:58 Early life mischief and finding skateboarding 03:32 Understanding transitions and success 05:57 Realizing it was time to leave skateboarding 06:38 Becoming a beginner in filmmaking 10:46 Family influence and unconventional paths 13:16 Work ethic creativity and self reliance 15:19 Learning from surfer elders 16:59 Following what you love in midlife 18:41 Giving your gift and letting it go 20:00 Embracing vulnerability and being a kook 24:10 Facing fear of being too old 28:00 Flow challenge and skill 31:10 MEA workshops experience 34:25 Quiet rebellion and midlife dreams 37:05 Listening intuition and creating space 39:05 Letting go of control 41:23 Daily practices for vitality 42:46 Harmonizing heart and mind 43:07 The power of listening 44:51 Closing reflections and gratitude Learn more about MEA at ⁠https://www.meawisdom.com/ #StacyPeralta #MidlifeReinvention #ModernElder #PersonalReinvention #MidlifeTransition #GrowthMindset #CreativeLife #LettingGo #SecondAct #PurposeInMidlife #LifeTransitions #DogtownAndZBoys #SkateboardingLegend #BecomingABeginner #Intuition

In this Wisdom Wednesday episode, Chip Conley, entrepreneur, author, and founder of MEA, opens up about the quiet disappointment many high achievers feel after they’ve “made it.” Through stories from building iconic companies, guiding Airbnb’s founders, and navigating midlife reckoning, Chip explores the success treadmill, and why chasing the next win so often leaves us unsatisfied. In this conversation, you’ll learn: - Why success can feel addictive but never fulfilling - The crucial difference between happiness and joy - How a simple gratitude practice can change how life feels day to day - What midlife teaches us about meaning, ego, and impact Thoughtful, honest, and deeply human, this episode is an invitation to pause, reflect, and reconnect with what actually matters. 👉 Watch now and step off the success treadmill. Timestamps: 01:00 Holiday plans and family time 01:51 MEA Film Festival vision and growth 04:28 Defining success and ambition 06:30 Happiness vs. Joy 10:03 Making gratitude intentional 11:27 Realizing the success treadmill 15:21 Ego shift at Airbnb 16:32 Getting off the treadmill sooner 16:50 Near death experience and perspective 18:30 Service as gratitude practice 19:40 Facing illness and loss 21:33 This too shall pass 21:49 Collective gratitude and closing Learn more about MEA at ⁠https://www.meawisdom.com/ #SuccessTreadmill #GratitudePractice #MidlifeWisdom #FindingMeaning #HappinessVsJoy #PersonalGrowth #MidlifeTransformation #RedefiningSuccess #LifePurpose #InnerFulfillment #ChipConley #MidlifeCrisis #SelfReflection #LifeLessons #MindfulLiving

What if the real risk in midlife isn’t change but staying comfortable? In this episode of Midlife Chrysalis, Chip Conley sits down with Dr. Margie Warrell, global expert on courage and bestselling author of The Courage Gap, to explore why so many smart, capable people feel stuck and how to move forward with clarity and bravery. Drawing from her journey from a rural Australian farm to the world stage, Margie shares powerful insights on courage, reinvention, and choosing growth over safety. In this episode, you’ll learn: - Why comfort quietly keeps you stuck - The hidden “timidity tax” of playing it safe - The tension between belonging and becoming - Why courage is a decision, not a feeling - Simple ways to take braver action in midlife If you’re ready to stop circling what’s familiar and start stepping into what’s possible, this conversation is for you. 🎧 Watch now and choose courage over comfort. Timestamps: 00:05 Meet Margie Warrell 01:08 Margie’s rural upbringing 02:33 The horse story and learning courage 05:00 Traveling the world after university 06:33 Early adulthood and global moves 08:47 Trauma, healing, and transformation 09:51 Life now and current work 11:05 Why courage is difficult 13:26 Becoming versus belonging 16:40 Regret and missed chances 21:19 Courage as action, not feeling 23:42 Closing the courage gap 23:42 Reset your focus 29:10 Challenge your certainty 33:50 Take the chance 36:13 Real-life courage breakthroughs 39:05 Courage, anxiety, and connection 42:34 Wisdom bumper sticker Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeCrisis #CourageOverComfort #PersonalGrowth #LifeTransitions #MidlifeReinvention #LeadershipMindset #SelfDevelopment #EmotionalResilience #FindingPurpose #SecondHalfOfLife #FearAndGrowth #AuthenticLiving #WomenInLeadership #BraveLiving #TheCourageGap

Dating in midlife can feel strangely hard, even when you’ve done the work, built a full life, and know yourself better than ever. If you’ve ever thought, “Why is this still so complicated?” this episode is for you. In this conversation, I sit down with Rachel Greenwald, Harvard MBA and veteran matchmaker who has helped guide nearly 1,000 marriages. With warmth, humor, and deep insight, Rachel reframes dating not as luck but as a learnable skill, especially in midlife. Together, we explore: - Why the people who make us happiest don’t always match our dating checklists - How chemistry can fool us and what actually leads to lasting connection - The quiet dating rules that keep smart people single - Why love often shows up in unexpected packages - How modern couples are redefining partnership, including living apart together This is a hopeful, practical conversation about dating with wisdom, curiosity, and openness, not fear or frustration. 👉 Listen or watch now and discover why midlife may be your most meaningful, and romantic, chapter yet. Timestamps: 00:46 Meet matchmaker Rachel Greenwald 03:36 From Harvard MBA to professional matchmaker 04:03 A midlife pivot that changed everything 07:29 The highs and lows of matchmaking 09:44 What is keeping people single 10:20 The most powerful question in dating 13:11 Chemistry vs compatibility & happiness 17:11 Why we repeat unfinished relationship patterns 19:46 Why dating checklists can backfire 22:39 Why men make up most matchmaking clients 25:08 Why parents hire matchmakers for young adults 28:03 Why midlife dating isn’t hopeless 35:57 The three must-haves that really matter 38:26 Living apart together and modern relationships 44:51 Inside the Santa Fe dating workshop 48:27 Wisdom bumper sticker 53:11 Final takeaways on love and dating in midlife Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeDating #DatingAfter40 #DatingAfter50 #MidlifeRelationships #FindingLoveLaterInLife #DatingAdvice #ModernDating #RelationshipAdvice #DatingWisdom #MidlifeWomen #MidlifeMen #Matchmaking #LoveAfterDivorce #DatingOver40 #MidlifeChrysalis

Feeling stuck in midlife? You might be in your chrysalis, not a crisis. In this Wisdom Wednesday episode, Chip Conley breaks down why midlife often feels confusing and heavy, and why that “messy middle” is actually the beginning of real transformation. Chip shares: • The three stages of every transition and where most people get stuck • What really happens inside the messy middle • Why men and women experience midlife so differently • How transitional intelligence (TQ) helps you move forward with clarity If you’re wondering whether something is wrong, or whether you’re simply evolving, this episode offers the reassurance and perspective you need. If you enjoyed this, follow the show, leave a rating, and join us next week for more Wisdom Wednesday insights. Timestamps: 00:00 Film Festival & Holiday Mood 01:55 Crisis vs Chrysalis and the Hollywood Myth 05:15 The Three Stages of Transition 07:07 Emotions in the Messy Middle 09:33 Finding Your Through Line 11:21 Ritualizing Endings 13:16 How Men Experience Midlife 15:40 How Women Experience Midlife 15:53 Why Women Navigate Midlife Differently 19:27 Identity, Purpose, and Feeling Stuck 21:35 Chip’s Personal Midlife Story 22:42 Why Men Resist This Work Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeChrysalis #MidlifeTransition #MidlifeCrisis #MessyMiddle #PersonalGrowthJourney #LifeTransitions #ChipConley #TransitionalIntelligence #MidlifeWisdom #SelfDiscovery #MidlifeWomen #MidlifeMen #EmotionalWellbeing #LifeReinvention #GrowthMindset

What if midlife became your chance to ROAR, not retire? In this powerful conversation, bestselling author and longevity visionary Michael Clinton shares why your 40s, 50s, and beyond are actually the most exciting and opportunity-filled decades of your life. From his rise to the top of Hearst Magazines to running marathons on seven continents and earning a new degree at 67, Michael reveals how reinvention is not only possible, it’s essential. He breaks down the ROAR framework for reimagining your future, explains why “life layering” is the antidote to midlife crisis, and dives into the emerging world of longevity science, age-positive culture, and purpose-driven living. If you’ve ever wondered what’s next, or what’s possible, this episode shows you how to build a richer, more meaningful second half of life. Watch now and start reimagining what your future can be. Timestamps: 00:00 Michael’s Santa Fe moment 01:31 Early life, father’s influence, love of words 05:27 A career in publishing 08:02 Midlife awakening at 39 10:50 Climbing Kilimanjaro and building an adventurous life 12:32 Returning to school at 67 15:56 The ROAR framework begins 20:00 Ageism, language shifts, modern role models 25:13 Life layering and building new identities 27:45 Preparing for post-career life 29:01 Reinvention stories and reimagineers 30:51 Relationships, editing your circle, and support systems 35:25 Growth mindset and lifelong curiosity 37:33 Longevity insights and the next book 39:18 Why longevity is having a cultural moment 44:01 Why the US is falling behind on lifespan 45:22 Rethinking work, age diversity, and longer careers 49:56 Longevity clinics and new health models 52:57 Longevity travel and residential communities 54:35 Wisdom bumper sticker Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeReinvention #Longevity #PurposeAfter50 #ReimaginingAging #LifeLayering #ROARMethod #SecondHalfOfLife #HealthyAging #MidlifeAwakening #RewireNotRetire #AgingWell #LiveLongerBetter #MidlifeTransformation #ModernAging #LifelongLearning

Ever wondered why some people get stronger, wiser, and more grounded with age? In this powerful conversation, Laird Hamilton and Gabby Reece reveal why midlife is actually the most dynamic, resilient, and liberating season of life. They open up about growing up on islands, how they met, what keeps their partnership strong, and why presence, patience, and community matter more than ever. From breathwork and injury recovery to identity shifts, parenting, and purpose, they share the hard-earned wisdom that helps them stay grounded, strong, and deeply connected. If you’re ready to see midlife as a chrysalis, not a crisis, this episode is for you. Watch now. Timestamps: 00:00 Welcome 00:09 Childhood and Island Upbringing 05:06 How Gabby and Laird Met 09:24 Navigating Two Athletic Careers 14:26 Relationship with Your Aging Body 21:46 Breathwork and Training Philosophy 26:04 Books and Science Behind Breathwork 29:42 Midlife Crisis vs Midlife Chrysalis 37:59 What Gets Better With Age 41:51 Relationship With Risk and Mortality 45:36 Presence and Stillness 51:47 Wisdom Bumper Sticker 54:17 Closing Remarks Learn more about MEA at ⁠https://www.meawisdom.com/ #LairdHamilton #GabbyReece #MidlifeWisdom #MidlifeChrysalis #HealthyAging #LongevityLifestyle #BreathworkTraining #MindBodyHealth #MidlifeTransformation #AgingWell #PeakPerformance #AthleteMindset #MidlifeGrowth #ModernElder #ChipConley

What if the secret to living longer isn’t in your genes… but in your mindset? In this Wisdom Wednesday episode, Chip Conley reveals the surprising research showing how a simple shift in how we think about aging can add years—yes, actual years—to our lives. From Becca Levy’s longevity findings to Carol Dweck’s growth-mindset principles, Chip breaks down why curiosity, openness, and lifelong learning may be the real fountain of youth. You’ll learn why “I’m too old to…” is one of the most dangerous beliefs we carry, how anticipated regret can propel us into action, and why midlife is actually one of the most powerful stages for reinvention. If you’re ready to rethink what’s possible in your next chapter, this episode will change how you see aging forever. Tune in now and start shaping the mindset that shapes your life. Timestamps: 00:00 Canadian spelling banter 02:56 Shifting mindset on aging 05:59 Anticipated regret as motivation 07:50 Lifelong learning and curiosity 10:09 What gets better with age 11:21 You’re not “too old” for anything 14:18 Mindset as invisible life framework 15:40 Weekly mindset assignment and closing remarksWhich of the 12 Reasons Most or Least Resonates With You? https://chipconley.com/reasons-quiz/ Learn more about MEA at ⁠https://www.meawisdom.com/ #wisdomwednesday #midlifegrowth #agingmindset #growthmindset #proaging #lifelonglearning #longevitymindset #chipconley #meaprogram #mindsetshift #curiosityasapower #midlifetransitions #positiveaging #mindsetmatters #livebetterlonger

What if everything you’ve believed about midlife is completely outdated? In this powerful conversation, Marianne Williamson sheds light on the truth about aging, visibility, and what it truly means to enter the second half of life with purpose. She shares raw reflections on menopause, identity shifts, modern rites of passage, and why midlife is less a crisis and more a spiritual turning point. Marianne also speaks about wisdom, reinvention, societal expectations, and how embracing your “third chapter” can unlock a deeper, more courageous version of yourself. If you’re ready to rethink aging and step into your next chapter with clarity and confidence, watch the full episode now. Timestamps: 00:00 Midlife awakening as unmapped territory 01:16 Aging, visibility, and grief for past identities 04:30 Rites of passage and communal transitions 08:13 Policy, culture shift, and public support 11:49 Government support for wisdom schools 13:06 Reflections on running for president 18:34 Midlife crisis vs chrysalis 19:14 Phase transition of society 21:31 Pattern recognition, memory, and wisdom 24:40 Teaching wisdom to younger generations 27:45 Family patterns, shadows, and generational conditioning 34:43 “Our deepest fear” and women’s empowerment 38:59 Cellular memory of witch burning 41:38 Sisterhood, bravery, and supporting each other 43:56 Re-inspiring midlife and visibility as women age 47:00 Presence, faith, and receiving life’s lessons 49:16 Chapter three as a crescendo 50:52 Midlife as a call to the soul 52:04 Wisdom bumper sticker Learn more about MEA at ⁠https://www.meawisdom.com/ #midlifeawakening #midlifecrisis #midlifewomen #agingwell #spiritualgrowth #womenswisdom #reinvention #mariannewilliamson #midlifetransformation #menopausejourney #mindfulnesspractice #lifepurpose #selfreinvention #modernelder #innerwisdom

What if living to 100 is more realistic than you think? Longevity expert Dan Buettner breaks down the real habits behind the world’s longest-living people, from food and movement to purpose, community, and stress relief. He explains why Americans age faster, what actually adds years to your life, and how simple daily choices can transform your future health. A simple, science-backed path to your best chapter yet. Watch now. Timestamps: 01:25 What society gets wrong about aging 04:05 Dan’s early life and big expeditions 06:33 Why anti-aging shortcuts don’t work 09:10 Proven habits for longevity 15:42 The alcohol debate and new research 18:56 Benefits of drinking moderately 21:29 Why 65 isn’t “old” anymore 25:02 What the US gets wrong about health 28:51 Processed food, inactivity, and social media 30:52 Blue Zones work in US cities 35:13 What’s happening in original Blue Zones 37:40 New insights for Dan’s next book 39:59 Dan’s divorce and midlife chrysalis 42:31 How Blue Zones became a concept 46:17 What Dan would regret not doing 48:45 Dan’s experience at MEA 51:07 Netflix series and frozen meals success 51:58 Wisdom bumper-sticker 55:19 The role of humility and aging 55:59 The need for a rite of passage at 50 56:19 Why midlife can be the best stage of life Learn more about MEA at ⁠https://www.meawisdom.com/ #BlueZones #Longevity #DanBuettner #HealthyAging #LiveLonger #HealthSpan #MidlifeChrysalis #AgingWell #LongevitySecrets #LiveTo100 #HealthyLiving #PurposefulLiving #HolisticHealth #LifestyleMedicine #Wellbeing

What if midlife is actually the start of your happiest years? In this episode, Chip Conley and Derek Gehl break down why life often gets better after 50, from rising emotional intelligence and deeper wisdom to feeling more like your true self. Chip explains why “growing whole” matters more than “staying young,” how Carl Jung’s insights can reshape your mindset, and why a pro-aging outlook can change your health, relationships, and purpose. If you want a fresh, hopeful take on midlife, don’t miss this conversation. Watch now. Tune in, and take the quiz! 👇 https://chipconley.com/reasons-quiz/"The Midlife Checkup Quiz" Timestamps: 00:00 Welcome to Wisdom Wednesday 03:12 Beauty of Santa Fe winters 03:15 Introducing Chip’s book 04:32 Growing whole as we grow older 06:31 Integrating all parts of ourselves 07:46 Stories about aging from Chip’s parents 09:18 Why Chip founded MEA 11:20 Midlife Checkup Quiz 12:07 Time affluence and midlife 14:29 Creating a pro-aging friend group 16:34 Closing thoughts Learn more about MEA at ⁠https://www.meawisdom.com/ Which of the 12 Reasons Most or Least Resonates With You? https://chipconley.com/reasons-quiz/  #MidlifeWisdom #ProAging #AgingWell #MidlifeGrowth #UCurveOfHappiness #EmotionalIntelligence #LifeAfter50 #MidlifeTransformation #HealthyAging #ChipConley #MidlifeMindset #PersonalGrowthJourney #WisdomWednesday #IdentityGrowth #MEACommunity

What happens when Don Lemon gets truly unfiltered? In this heartfelt, funny, and deeply honest conversation, Don opens up about aging with confidence, coming out in midlife, letting go of old shame, and the freedom that comes from no longer needing anyone’s approval. We talk about identity, love, sex, wisdom, and why his mantra “old people be knowing” captures the real gift of growing older. Don also reflects on the state of media, the “prime” controversy, and how stepping away from traditional news helped him reclaim his voice and his joy. If you’re ready for truth, evolution, and a warm reminder that life after 50 can get better, tune in. Watch now. Timestamps: 00:00 Chip’s episode opening 00:57 Don on aging and happiness 02:34 Don’s childhood and early years 03:38 Politics, Reagan, and identity 06:52 Dating while closeted 09:52 College years and social life 12:17 First gay bar experiences 16:20 Don’s coming-out story 19:47 Coming out publically in a book 21:41 Midlife chrysalis and confidence 25:10 What gets better with age 28:28 The “prime” controversy explained 34:07 State of media and independence 36:30 Politics, division, and future outlook 37:26 Don on never retiring 38:49 Possible regret 10 years from now 40:24 Don’s wisdom bumper sticker 43:543 Judy Garland and music icons 46:50 Chip’s reflections Learn more about MEA at ⁠https://www.meawisdom.com/ Keywords: #DonLemon #midlife #agingwell #lifeafter50 #midlifefreedom #midliferenaissance #comingoutstory #lgbtqstories #authenticitymatters #selfacceptance #personaltransformation #midlifewisdom #findingyourvoice #reinventyourlife #unfilteredconversation

Grief isn’t just an emotion, it’s energy that lives in the body until we face it. I sit down with Meghan Jarvis, a trauma therapist and grief mentor who’s helped countless people find their way through loss. Meghan shares her own story of heartbreak, how grief and trauma intertwine, and the six simple practices she teaches to move that heavy energy through the body and back toward healing. We also talk about midlife transitions, why so many of us feel stuck, and how community can bring us back to life. 👉 Tune in for a real, hopeful conversation about what it truly means to grieve, heal, and grow. Timestamps: 00:00 Childhood loss that led her to grief work 02:13 Uncovering long-buried trauma 06:02 What trauma teaches about safety and fear 09:29 Grief as energy moving through the body 11:07 How stored grief affects physical health 13:02 Losing her parents and lessons learned 17:29 Checking into treatment and finding purpose 19:32 The vagus nerve and how the body heals 22:19 Midlife transitions and hidden grief 24:18 Helping clients rewrite their stories 26:12 The six pillars of the Grief Mentor Method 31:11 Mindfulness, nourishment, and rituals for healing 39:13 Why midlife brings old losses back 42:21 Signs of unresolved grief 43:55 Finding meaning and joy after healing 47:43 MEA as a space for renewal 51:44 Meghan’s wisdom bumper sticker Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeHealing #GriefJourney #EmotionalHealing #MeghanJarvis #LifeTransitions #MidlifeGrowth #HealingAfterLoss #MindBodyConnection #GriefSupport #TraumaRecovery #FindingPurpose #PersonalGrowth #MidlifeAwakening #MentalHealthAwareness #ChipConley

What if everything you’ve believed about aging and retirement is wrong? In this week’s Wisdom Wednesday, Chip and Derek dive into the surprising truth about aging. Why retirement often makes us less healthy, how community and purpose keep us alive longer, and why our “crystallized intelligence” actually gets stronger well into our 60s and 70s. They explore the real ingredients of a meaningful midlife, the magic of third-vault conversations, and the stories of people who’ve traded old scripts for more inspired lives. If you’re ready to feel hopeful, energized, and a little more excited about the years ahead, watch the full episode. Timestamps: 00:00 Intro 00:34 Welcome to Wisdom Wednesdays 01:43 The origins of age 65 retirement 02:59 How retirement affects lifespan 04:08 Fluid intelligence vs crystallized intelligence 06:01 What people need the most after 50 08:27 Chip’s own “mini retirement” 10:07 Rethinking the three-stage life 11:58 The litigator who became a baker 14:11 Keeping your options open 16:15 Changing habits by changing habitat 17:16 The concept of the third vault 20:12 Deeper conversations with aging 20:56 Episode wrap-up and closing remarks Learn more about MEA at ⁠https://www.meawisdom.com/ #midlifechrysalis #agingwell #longevitymindset #midlifetransformation #purposeafter50 #crystallizedintelligence #rethinkingretirement #healthyaging #midlifewisdom #lifepurpose #aginggracefully #lifestages #livingto100 #midlifecommunity #wisdomwednesdays

Ever wonder if slowing down might actually wake you up? In this episode, I sit down with Susan Cain, the bestselling author of Quiet and Bittersweet, to talk about the hidden strengths of introverts, the surprising beauty in melancholy, and why midlife can be the most creative and peaceful chapter of your life. We dig into what it really means to live with depth, authenticity, and joy, without the noise. ✨ Hit play and join us for a quiet conversation that might just change how you see yourself. Timestamps: 00:18 The Quiet Life Community 01:23 Susan’s early career as a corporate lawyer 02:18 Realizing law wasn’t her path 03:25 The success of Quiet and its life-changing impact 06:09 Defining introversion and extroversion 09:43 Chip’s story: from introvert to social alchemist 11:35 Why people grow more introverted with age 13:24 Reputational confusion and being open 17:56 What is “Worktrovert” 20:17 Deeper happiness through the bittersweetness 23:05 Daily practices to balance beauty and melancholy 25:44 The power of remembering mortality 27:45 Chip’s near-death experience and slowing down 30:31 Slowing life down in midlife and releasing ambition 33:01 Leaving law and embracing a quiet, creative life 38:31 How awareness of death deepens appreciation for life 40:53 What Susan’s working on now 43:07 Liz Gilbert’s TED Talk and creative pressure 45:50 Susan’s advice for aspiring writers 49:41 Wisdom bumper sticker Learn more about MEA at ⁠https://www.meawisdom.com/ #SusanCain #ChipConley #MidlifeChrysalis #QuietLife #Introversion #Bittersweet #SelfDiscovery #MidlifeTransformation #EmotionalIntelligence #PersonalGrowth #QuietPower #LifeTransitions #MindfulLiving #AuthenticLife #CreativityAndCalm

What happens when two New York City professionals lose their jobs, move to a tiny rural town, and accidentally build one of America’s most beloved skincare brands? Brent and Josh of Beekman 1802 reveal how kindness, community, and old-fashioned wisdom became the backbone of their business and their midlife reinvention. They share how loving your neighbor can be a real strategy, why contentment matters more than achievement, the 51% rule that keeps their partnership strong, and how better aging starts with simple kindness to yourself and others, all delivered with warmth, wisdom, and humor. 👉 If you’re ready for a kinder, clearer way to think about midlife, just press play. Timestamps: 00:00 Intro 00:59 Meet Brent & Josh of Beekman 1802 02:47 How Brent & Josh met 04:18 Brent’s upbringing & coming out journey 06:01 Becoming goat farmers & starting Beekman 1802 07:19 How the brand got its name 09:09 Turning a recession into a business opportunity 10:35 Growing from homemade soap to a global brand 12:54 The idea behind Goat Wisdom book 16:33 Their favorite principles 20:46 Community, kindness & homophobia 25:38 Brent’s family and true Christian acceptance 28:41 Being partners in love and business 29:56 The 51% Rule for decision-making 32:06 Radical transparency as kindness 34:37 Personal midlife philosophies 38:42 What they’d regret in 10 years 40:36 Redefining success as contentment 41:55 “Better aging,” social connection & kindness 45:16 Farm wisdom for life 48:56 Wisdom bumper stickers 52:12 Chip’s closing reflections Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeTransformation #GoatWisdom #Beekman1802 #ChipConley #MidlifeChrysalis #BetterAging #KindnessCulture #EntrepreneurJourney #LifeReinvention #ContentmentOverAchievement #LGBTQEntrepreneurs #ModernElders #AgingWisdom #MidlifeReinvention #SmallTownStories

In the very first episode of Wisdom Wednesdays, Chip Conley and Derek Gehl sit down for a thoughtful, honest conversation about what wisdom really means in midlife. Chip shares the down-to-earth definition that guides his life and talks about the small, consistent practices that help him turn everyday experiences into something meaningful. If you’re ready for conversations that spark growth, clarity, and courage… ▶️ Start with Episode 1 and begin your wisdom journey with us. Timestamps: 00:00 Intro 00:22 Welcome to Wisdom Wednesdays 01:37 What is wisdom and why it matters 02:55 Life lessons as raw material 03:32 Mindfully sharing wisdom 05:28 Can wisdom be cultivated 08:06 The problem with AI wisdom 08:51 The chef metaphor 10:52 Wisdom during cancer treatment 12:51 Chip’s wisdom bumper sticker 14:12 How to start your wisdom practice 15:54 Final reflection Learn more about MEA at ⁠https://www.meawisdom.com/ #WisdomWednesdays #ChipConley #MidlifeChrysalis #MidlifeWisdom #PersonalGrowthJourney #ModernElder #LifeLessons #MidlifeTransformation #EmotionalWellbeing #MindfulLiving #SelfAwareness #MidlifePurpose #JournalingPractice #InnerGrowth #ThrivingInMidlife

Midlife isn’t a crisis. It’s your greatest awakening. In this inspiring episode, gerontologist and coach Barbara Waxman redefines aging through the lens of “Middleessence,” a stage of growth, purpose, and renewal. She reveals how to reclaim energy with her Energy Audit, why mindset matters more than genetics for longevity, and how lifestyle medicine helps you live undiminished at every age. ✨ Learn how to flourish, not fade, in your next chapter. ▶️ Watch now on YouTube or listen on Apple Podcasts. Timestamps: 00:00 Meet gerontologist Barbara Waxman 00:28 How she became a gerontologist 02:56 What is “middle essence” 07:18 Adolescence vs. middle essence 13:37 Why happiness rises after 50 16:42 Debunking the midlife crisis myth 18:53 Redefining legacy and purpose 20:19 Barbara’s own midlife awakening 23:03 What is the Energy Audit 24:36 What lifestyle medicine really means 28:55 The 7 lifestyle levers for thriving 30:42 Mindset’s power in longevity 32:41 Mindset studies that changed lives 35:18 Well-being burnout explained 36:23 Self-care vs. self-indulgence 38:10 Solitude, introverts, and renewal 40:09 Unlocking longevity and the third span 45:46 Living undiminished and flourishing 46:49 Wisdom bumper sticker Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeChrysalis #BarbaraWaxman #MidlifeTransformation #MiddleEssence #LongevityMindset #HealthyAging #LifestyleMedicine #WomenOver40 #LifeTransitions #PersonalGrowth #MindsetShift #AgingWell #HumanFlourishing #EnergyAudit #PurposefulLiving

What if aging isn’t about decline, but about becoming more alive than ever? The bestselling author and spiritual teacher Mark Nepo opens up about how surviving cancer reshaped his entire understanding of life, creativity, and purpose. He reveals the wisdom behind The Fifth Season, a time in life when the inner world begins to shine brighter than the outer one, and shares how to live and create with authenticity in midlife and beyond. Mark’s reflections will move you, ground you, and remind you what it truly means to be present, wholehearted, and free. 🎧 Watch now and rediscover how beauty, suffering, and friendship all become part of life’s greatest art: your own becoming. Timestamps: 00:00 Intro 00:23 The Fifth Season: Creativity in midlife 04:10 What the “Fifth Season” really means 05:28 How cancer changed Mark’s life 09:58 Facing death and finding purpose 12:00 What cancer taught him about life 13:18 Chip’s own cancer story 17:10 Realizing he was a poet 22:14 How Oprah discovered his book 24:47 Success, humility, and staying grounded 29:59 Mark’s Pirouettes poem 34:32 Creativity as a spiritual act 42:17 Aging and letting go of old identities 43:26 The tea ceremony and making lists 46:30 The poetry of friendship 51:14 Teaching at MEA 55:12 Free Fall poem 56:03 Wisdom bumper sticker Learn more about MEA at ⁠https://www.meawisdom.com/ #MarkNepo #TheBookOfAwakening #TheFifthSeason #MidlifeChrysalis #ChipConley #MidlifeWisdom #SpiritualGrowth #MidlifeCreativity #PersonalTransformation #CancerSurvivor #MindfulnessJourney #AgingGracefully #PurposeInMidlife #SpiritualAwakening #PoetryOfLife #OprahBookClub #SoulWork #LivingFully #EmotionalHealing #AuthenticLiving

🔥 One night on air changed everything for Tamsen Fadal. She was at the top of her game as a TV anchor when she suddenly started forgetting words and sweating through live broadcasts, without realizing she was entering menopause. That moment became the turning point that led her from journalism to advocacy. In this conversation, Tamsen shares how she turned confusion into purpose, launching The M Factor documentary and her book How to Menopause. ✨ Join us as we talk about redefining midlife, breaking the silence, and helping women everywhere navigate this powerful new chapter. Timestamps: 00:43 Early Life and Losing Her Mother 02:44 Lessons from Her Mother and Family Values 04:06 Breaking Into TV News and Facing Stereotypes 07:11 Sexism and Ageism in the Media Industry 09:12 Defining Her On-Air Brand and Early Career Years 11:46 Moving to New York and Personal Life Changes 15:36 Advice to Her 40-Year-Old Self 17:01 Health Issues, Misdiagnosis, and Menopause 23:28 TikTok & Creating Awareness 25:29 Street Interviews, Documentary, and The Book 30:28 Understanding Perimenopause and Menopause 34:16 Hormone Therapy and Medical Education Gaps 36:35 Finding Certified Menopause Practitioners 38:48 How Men and Coworkers Can Be Supportive 41:25 Reframing Midlife and the “Bolden Years” 44:37 Purpose, Creativity, and Daily Motivation 46:28 Redefining Retirement and Lifelong Energy 48:22 Wisdom Bumper Sticker Learn more about MEA at ⁠https://www.meawisdom.com/ #MenopauseAwareness, #Perimenopause, #MidlifeEmpowerment, #WomensHealth, #MenopauseSupport, #MenopauseEducation, #TamsenFadal, #ChipConley, #HowToMenopause, #TheMFactor, #MidlifeCrisisMyth, #BoldenYears, #HormoneTherapy, #MenopauseAdvocate, #MidlifeReinvention

What if awe was the secret ingredient to happiness? 🌿 In this episode, I sit down with UC Berkeley psychologist Dacher Keltner to explore how awe, compassion, and moral beauty can transform the way we live and age. We dive into the science of wonder — from the power of collective joy to how simple “awe walks” can boost your health, purpose, and connection. ✨ Join us as we uncover why we’re truly born to be good and how awe might just be the key to midlife renewal. 🎧 Tune in for the full conversation and get inspired to see life with fresh eyes. Timestamps: 00:00 Chip welcomes Dacher and reflects on their friendship 00:18 Why people smile when they talk about Dacher 01:06 How early experiences shaped his empathy 03:32 Journey into psychology and emotion science 06:42 Discovering emotion in the human face 07:31 Writing Born to Be Good and redefining human nature 09:42 Science of compassion, gratitude, and kindness 13:15 How the study of awe began 14:17 What awe is and how it feels 18:24 Collecting awe stories from around the world 20:33 The eight wonders of awe 21:00 Collective effervescence and shared joy 23:44 Synchronizing with others through movement and emotion 25:01 How screens disrupt human connection 27:00 Moral beauty and the power of witnessing goodness 31:32 Moral beauty within community and everyday life 32:39 Awe and moral beauty in midlife 36:33 The Awe Walk study and its health benefits 39:47 Finding awe in daily moments 41:25 Inside Dacher’s “Cultivating Awe” workshop 43:51 Practicing awe through grief and gratitude 45:09 Wisdom bumper sticker: seeing hidden beauty in people 47:35 Love (agape) as the essence of awe 49:10 Closing reflections and gratitude Learn more about MEA at ⁠https://www.meawisdom.com/ #awe #DacherKeltner #ChipConley #MidlifeChrysalis #CultivatingAwe #BornToBeGood #MoralBeauty #CollectiveEffervescence #ScienceOfAwe #HumanConnection #Mindfulness #EmotionalIntelligence #MidlifeWisdom #GratitudePractice #FindingPurpose

What happens when one of the NFL’s most celebrated athletes walks away from fame, fortune, and the life everyone else wanted for him? In this powerful episode, Ricky Williams, now known as Errick Miron, opens up about his transformation from Heisman Trophy winner to healer, teacher, and astrologer. He shares how depression, self-discovery, and spirituality reshaped his identity and helped him find peace beyond the game. If you’ve ever wondered what it truly means to let go and start over, this conversation will change the way you think about success, purpose, and freedom. 🎧 Listen now and discover how Ricky Williams became Errick Miron and found his true self. Timestamps: 00:42 Early Ambitions and Upbringing 02:19 Choosing the University of Texas 04:54 College Glory and the Heisman Dream 07:37 NFL Reality Check 10:00 Mental Health and Identity Crisis 15:00 Discovering New Passions 16:14 Leaving the NFL & Coming Back 19:47 Journey to Australia and Discovering Ayurveda 22:32 First Encounter with Astrology 24:26 Return to Football with New Purpose 26:31 Preparing for Life After Sports 29:02 Retirement & Going Back to Astrology 38:41 Evolutionary Astrology Explained 42:46 Meeting His Wife & Becoming Errick Miron 47:21 Redefining Masculinity 49:42 Upcoming Workshop: Evolving Identity 52:16 Wisdom Bumper Sticker Learn more about MEA at ⁠https://www.meawisdom.com/ #RickyWilliams #ErrickMiron #MidlifeChrysalis #EvolvingIdentity #NFLtoAstrology #MentalHealthJourney #SpiritualAwakening #HealingJourney #AthleteTransformation #AstrologyForGrowth #LifeAfterSports #SelfDiscovery #PersonalGrowth #MasculineHealing #MindfulnessInMidlife

What if the path to a meaningful life had nothing to do with fame or success and everything to do with service and soul? In this captivating conversation, Rainn Wilson opens up about his transformation from Hollywood ego to spiritual seeker, sharing how faith, meditation, and humility helped him rediscover purpose beyond the spotlight. Together with Chip Conley, he explores why midlife can be a sacred turning point when the soul finally takes the lead. 👉 Watch now to learn how Rainn’s journey can help you reconnect with your own soul. Timestamps: 00:00 Introduction 02:55 What Is a Soul? 05:52 Chip‘s Definition of Soul 08:18 Humans on a Spiritual Journey 09:32 Growing Up Baha’i 13:58 The 1960s Spiritual Revolution 17:31 Hollywood, Faith & the Dark Night of the Soul 21:01 Becoming Dwight Schrute 22:50 Famous in Midlife 29:01 The Ego and Hollywood 31:38 Letting the Soul Lead 34:08 Devotion & Daily Practice 40:03 The Soul Boom Workbook 42:24 How the Workbook Came to Be 44:41 Wisdom Bumper Sticker 49:24 Chip’s Reflections and Takeaways Learn more about MEA at https://www.meawisdom.com/ #RainnWilson #SoulBoom #MidlifeChrysalis #ChipConley #SpiritualRevolution #Bahaifaith #SoulJourney #ModernSpirituality #EgoAndSoul #Mindfulness #PersonalGrowth #MentalHealthAwareness #ServiceAndPurpose #ConsciousLiving #SpiritualAwakening

What if the worst thing that ever happened to you became the very thing that set you free? 🌱 In this deeply moving episode, Dr. BJ Miller—physician, amputee, and palliative care visionary—shares how a near-fatal accident in college transformed his understanding of life, loss, and what it really means to live fully. From his journey through unimaginable pain to founding Mettle Health, BJ reveals how facing mortality can open the door to compassion, creativity, and peace. If you’ve ever feared aging, grief, or change, this conversation will completely shift your perspective. 👉 Watch now and discover how to turn life’s hardest moments into your greatest teachers. Timestamps: 00:00 Introduction 00:36 The Accident That Changed Everything 04:17 Processing Grief and Feeling “Seen” 09:27 Rebuilding Life in His 20s 14:46 From Art History to Medicine 16:24 Discovering Palliative Care 20:27 What Palliative Care Really Means 24:26 Spiritual Dimensions of Caregiving 27:16 What We Get Wrong About Death 29:42 Making All Healthcare Palliative 32:44 Founding Mettle Health 36:56 Advice for Caregivers 41:25 The Power of Grief 43:50 BJ’s Midlife Chrysalis 47:49 What People Regret Most Before Death 51:48 Dying as a Creative Act 55:25 Wisdom Bumper Sticker Learn more about MEA at ⁠https://www.meawisdom.com/ #BJMIller #MidlifeChrysalis #ChipConley #EndOfLifeCare #PalliativeCare #HospiceCare #GriefAndHealing #MidlifeWisdom #CaregivingJourney #FindingMeaning #LifeAndDeath #SpiritualGrowth #EmotionalResilience #MindfulLiving #AuthenticLife

Ever wondered what it really means to start over when the world thinks you’ve peaked? In this episode, Daniel Pink, bestselling author of Drive and The Power of Regret, reveals why midlife isn’t a crisis but a creative turning point. He talks about becoming a beginner again after 50, how regret can guide us toward what truly matters, and why lasting motivation comes from autonomy, mastery, and purpose, not paychecks. 👉 Watch now to learn how to reinvent yourself with clarity, courage, and curiosity. Timestamps: 01:15 Early Career & Al Gore Years 04:12 Leaving Politics for Book Writing 07:05 The Book “Drive” & Science of Motivation 11:10 Leadership & Purpose Within Organizations 14:13 Living an Average Mid-40s Reality 17:08 The Midlife Chrysalis & Year-Long Sabbatical 22:04 Writing for The Washington Post 25:58 Becoming a Rookie at 50 30:00 The Science of Timing 32:03 Evaluating Autonomy, Mastery & Purpose 34:21 How He Wrote “The Power of Regret” 37:42 The Wisdom in Regret 39:24 Anticipated Regret in Action 42:34 On Retirement & Regeneration 46:16 The Idea of Gap Year at 50 49:38 Regenerative vs. Retirement Communities 51:49 Upsides & Downsides of Aging 55:20 Dan’s Wisdom Bumper Sticker Learn more about MEA at ⁠https://www.meawisdom.com/ #DanielPink #ChipConley #ModernElderAcademy #MidlifeChrysalis #ThePowerOfRegret #DriveBook #AutonomyMasteryPurpose #MotivationScience #MidlifeReinvention #CareerReinvention #FindingPurpose #AgingWithPurpose #LifelongLearning #PersonalGrowth #MindsetShift

What happens when the person you love most slowly begins to disappear before your eyes? In this deeply emotional and inspiring conversation, Emma Heming Willis opens up about life with Bruce Willis following his diagnosis of frontotemporal dementia and how she turned heartbreak into purpose. Joined by Helen Christoni, co-founder of Make Time Wellness, the two reveal why women’s brain health is so often ignored, what every caregiver needs to hear, and how to rediscover joy even in the hardest seasons of life. 👉 Watch now and learn how making time for yourself might just be the most powerful act of care there is. Timestamps: 00:00 Intro 00:54 How Helen and Emma created Make Time Wellness 04:47 Hormones, estrogen loss, and dementia risk 06:03 Helen’s personal connection to dementia 08:04 Starting Make Time as Bruce’s symptoms appeared 08:51 How Emma met Bruce Willis and first signs of FTD 12:05 Understanding anosognosia and early dementia signs 15:29 The meaning of ambiguous loss for caregivers 18:45 Practical tools and exercises for caregivers 20:37 Redefining self-care and “making time” 21:20 How others can help caregivers in real ways 24:09 The caregiving crisis and policy change needed 28:43 Gender roles and men’s perspective on caregiving 31:00 Make Time Wellness mission and products 34:49 Bruce Willis’s current condition and progression 38:20 How their daughters are coping and family life 39:24 Emma’s and Helen’s advice for caregivers 40:57 Wisdom bumper sticker 44:57 Closing reflections and gratitude Learn more about MEA at ⁠https://www.meawisdom.com/ #EmmaHemingWillis #HelenChristoni #MidlifeCaregiving #WomensBrainHealth #CaregiverSupport #FrontotemporalDementia #DementiaAwareness #MakeTimeWellness #MidlifeResilience #SelfCareReimagined #MidlifeWisdom #WomenSupportingWomen #CaregivingJourney #FindingJoyAgain #ModernElderAcademy

What if everything you’ve been taught about happiness and success is upside down? In this episode of Midlife Chrysalis, Chip Conley talks with Arthur Brooks, Harvard professor, bestselling author, and former French horn prodigy, about his remarkable journey from the concert stage to the world of behavioral science. Together, they unpack why strivers burn out, how our brains shift from fluid to crystallized intelligence, and the simple formula that can turn midlife from a crisis into a transformation. Don’t miss this inspiring conversation. Listen now and start rethinking your own second curve. Timestamps: 00:00 Intro 01:06 Arthur Brooks’ origins and family background 02:59 Religious upbringing and conversion to Catholicism 04:56 Navigating academia and faith in secular environments 07:08 Early music training and struggles to become the best 13:06 Striver mentality and American entrepreneurship DNA 16:41 Leaving music for economics and behavioral science 20:52 Imposter syndrome and skills learned from performance 22:33 Becoming CEO of the American Enterprise Institute (AEI) 29:05 Burnout, midlife shift, and vital plane encounter 32:19 Plane encounter with a famous figure and reflection on decline 35:47 Realizing the need for a second curve 38:10 How we move from fluid to crystallized intelligence 42:43 Airbnb and the role of “modern elder” wisdom 45:02 Advice for shifting into careers built on crystallized intelligence 46:56 The danger of pride and Dante’s frozen Satan metaphor 49:40 Learning to want less: the secret to second-curve happiness 54:39 Editing life instead of accumulating - reverse bucket lists 55:55 Generativity, religion, and aging with meaning 57:16 Policy thoughts on midlife education and wisdom schools 1:01:59 Wisdom bumper sticker 1:05:28 Closing reflections from Chip Learn more about MEA at ⁠https://www.meawisdom.com/

What happens when a world-famous photographer nearly loses everything — and turns it into a movement redefining aging? In this powerful conversation, David Stewart shares his journey from shooting Vogue covers and working with Andy Warhol’s circle, to battling a life-threatening autoimmune disease that forced him to rethink everything. Out of crisis came transformation — and the creation of Ageist and Super Age, two platforms challenging stereotypes about aging and proving that purpose, health, and vitality don’t fade with time. Watch now to discover how to stay healthier, live longer, and embrace your true greatness. Timestamps: 00:00 Catching up: Manhattan, travel, and life during Covid 01:36 Childhood, school struggles, and proving people wrong 04:07 Studying engineering, switching to political science, and discovering photography 06:14 Declaring himself a photographer, early Vogue ad, and move to Paris 07:01 Life in New York: Andy Warhol’s scene, magazine covers, and big clients 08:02 Health crisis, autoimmune disease, and a year in hospital 10:00 Turning point: removing his spleen and changing lifestyle 11:01 The birth of Ageist: challenging age stereotypes in media and advertising 14:50 White-light moment with AT&T campaign and marketing blind spots 18:50 Age dysmorphia, beauty industry challenges, and why older audiences are complex 21:27 From Ageist to Super Age: growth, readership, and global impact 25:27 Health transformation and connecting mindset with the body 30:00 Teaching moments: embodied wisdom, confidence, and breaking limits 33:55 What Super Age does: informing, inspiring, and offering trusted tools 35:10 Longevity pillars: sleep, fitness, stress management, and community 37:31 Why grip strength and VO₂ max matter for longevity 41:42 Smart habits vs. fads: avoiding “dumb stuff” and focusing on basics 44:39 Managing stress, hormetic adaptation, and resilience 45:00 Why men chase longevity more than women 46:04 Thoughts on Brian Johnson and longevity biohacking 47:50 The future of health: AI-driven personalized medicine 51:28 Wearables: when they help vs. when they hurt 53:12 Passing wisdom to the next generation: embracing greatness and usefulness 56:15 Final reflections: passion, usefulness, and living as a contender Learn more about MEA at ⁠https://www.meawisdom.com/ #Longevity #HealthyAging #RedefiningAging #SuperAge #Ageist #MidlifeReinvention #MindsetMatters #AgingWell #LifeAfterCrisis #HealthTransformation #Vitality #BreakingAgingStereotypes #AgingStrong #LongevityLifestyle #AgelessLiving

What happens when a bestselling writer and a former corporate executive dive deep into life’s second half? In this powerful conversation, Anne Lamott and Neal Allen share raw, funny, and moving stories about midlife transformation, spiritual awakening, recovery, and how to finally silence that relentless inner critic. From faith and writing to intimacy, aging, and finding purpose, their wisdom will leave you inspired — and maybe even rethinking your own path. 👉 Don’t miss this chance to hear life-changing insights from two voices who know the journey inside out. Watch now and discover how midlife can become your most powerful chapter yet. Timestamps: 00:00 From Corporate Life to Spiritual Coaching 06:08 Annie’s Christian Spirituality 08:19 Annie’s Childhood, Religion & Humor 12:46 Embracing Christianity in a Ghetto Church 14:40 Annie’s Left-Wing Christianity Views 17:23 Anne’s Washington Post Columns on Aging 21:04 Imposter Syndrome & Life After 50 24:50 The Value of Intimacy & Deeper Connection 28:51 Taming the Inner Critic Workshop 33:46 Wisdom Bumper Stickers Learn more about MEA at ⁠https://www.meawisdom.com/ #AnneLamott #NealAllen #MidlifeChrysalis #SpiritualGrowth #LifeAfter50 #InnerCritic #WritingCommunity #RecoveryJourney #ChristianSpirituality #PersonalTransformation #MindfulnessPractice #AgingWisdom #SpiritualCoaching #SelfAwarenessJourney #FaithAndHealing

What if the most painful disruptions in life—illness, job loss, divorce, or even an empty nest, were actually the keys to growth? Bestselling author Bruce Feiler shares how “life quakes” shake up our stories and push us to rewrite them. From his own battle with cancer and family upheaval to studying hundreds of life transitions, Bruce reveals why resilience is a skill, not a trait, and how rituals, creativity, and storytelling can turn crisis into renewal. Dive into his powerful seven tools for navigating transitions, learn why the myth of the midlife crisis is outdated, and how to finally become the hero of your own story. ✨ Tune in to discover how to transform life’s hardest moments into your greatest turning points. Timestamps: 00:00 Intro 00:40 Introduction to Bruce Feiler 02:24 Background, early life & first book 07:09 Life quakes and losing control of your story 12:15 Knowing when a transition is complete 18:11 The three stages of transition 24:40 Seven tools for navigating transitions 30:31 Acceptance and rituals to mark change 35:18 The ritual renaissance & new book preview 41:28 Routine vs. ritual explained 45:09 Shedding habits & finding creativity 49:19 Updating your story & unveiling your new self 51:19 The debate: midlife vs. transitions at all ages 58:51 Wisdom bumper sticker 01:04:22 Closing reflections & gratitude Learn more about MEA at ⁠https://www.meawisdom.com/ #BruceFeiler #LifeQuakes #MidlifeTransitions #ReinventYourself #LifeIsInTheTransitions, #PersonalGrowth #OvercomingCrisis #FindingMeaning #ResilienceInMidlife #RewriteYourStory #RitualsAndRenewal #MidlifeReinvention #SelfDiscoveryJourney #ThrivingThroughChange #BeTheHeroOfYourStory

How do you survive when the person you can’t live without begins to destroy you? In this powerful episode of Midlife Chrysalis, Elizabeth Gilbert joins Chip Conley to share the raw story behind her new memoir, All the Way to the River. She opens up about walking alongside her partner through addiction and relapse, confronting her own patterns of codependency, and finding healing through recovery and surrender. It’s an honest, unfiltered look at love, loss, and what it really takes to stand on your own two feet. Tune in now to hear Elizabeth Gilbert as you’ve never heard her before. Timestamps: 00:00 Intro 00:40 Introduction to Elizabeth Gilbert 03:06 All the Way to the River book 06:06 Why it took 7 years to write 07:21 A forensic look at repeating patterns 10:36 Love vs. addiction in relationships 13:49 How Liz met Raya & their evolving bond 19:55 Confessing love during Raya’s illness 25:31 Grief, loss, and missing her friend 27:18 Writing in solitude & surrendering to truth 35:00 Surrender, recovery, and true powerlessness 41:21 Dark thoughts & God’s voice 45:15 What sex & love addiction means for Liz 51:36 12-step practices & six years of abstinence 54:35 Reflections on MEA and retreat power 58:22 Wisdom bumper sticker Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeChrysalis #ElizabethGilbert #AllTheWayToTheRiver #GriefJourney #AddictionRecovery #LoveAndLoss #Codependency #HealingFromTrauma #12StepRecovery #SexAndLoveAddiction #SpiritualGrowth #MemoirWriting #MidlifeWisdom #EmotionalSobriety #LifeLessons

What happens when one of America’s most celebrated pastors dares to question everything? In this unfiltered conversation, Rob Bell, once dubbed the “punk rock pastor” and author of the explosive bestseller Love Wins, opens up about the controversy that made him Christianity’s most talked-about heretic, why he walked away from his megachurch at the height of fame, and how midlife pushed him to reinvent himself. From faith and psychedelics to wisdom traditions, AI, and the art of living an unpigeonholable life, Rob’s journey is as provocative as it is inspiring. Whether you see him as a rebel, visionary, or outlaw, one thing’s clear: you won’t walk away from this episode thinking the same. Timestamps: 00:00 Intro 00:35 Meet Rob Bell 02:08 Following a Calling & Evolving 05:16 Early Life & First Sermons 11:04 Starting Mars Hill Church 13:02 Performance Art Preaching 15:01 Controversy & Pushback 16:44 Rise to Time’s 100 Most Influential People 21:10 Leaving the Church & Midlife Transition 26:25 Reinventing in His 40s 29:58 Evolving Faith & Moving Beyond Doctrine 31:46 The Greatest Unlearning 35:00 Surfing, painting & daily rituals 38:15 Reconnecting with Spirituality 40:25 On Psychedelics & Temples 44:57 From Knowledge to Wisdom 51:16 Redefining Intelligence 54:56 Rob’s Wisdom Bumper Sticker 57:47 Closing Reflections Chip shares key takeaways on creativity, freedom, and living beyond expectations. Learn more about MEA at ⁠https://www.meawisdom.com/ #RobBell #MidlifeChrysalis #PunkRockPastor #LoveWins #SpiritualJourney #MidlifeTransitions #FindingPurpose #WisdomTraditions #SpiritualAwakening #FaithAndCreativity #LeavingReligion #SpiritualGrowth #Unpigeonholable #MidlifeSpirituality #CareerEvolution

What if aging wasn’t about slowing down—but about leveling up? In this powerful conversation, Marc Freedman, founder of Encore.org (now CoGenerate), unpacks the surprising history of retirement, why communities like Sun City reshaped how we see aging, and how we can flip the script on what it means to grow older. From encore careers to intergenerational mentorship, Marc shows why midlife is no dead end—it’s a launchpad for purpose, impact, and connection. If you’ve ever wondered how to thrive after 50, find meaning in your “second act,” or simply stay relevant in a rapidly changing world, this episode will change how you see the road ahead. Timestamps: 00:00 Intro 00:39 Marc Freedman as Chip’s “modern elder” 02:46 How aging became feared, not revered 04:26 Why older people are no longer revered 07:30 Rise of retirement communities 13:14 Why people question retirement as a goal 15:56 Marc’s personal view on retirement 18:36 The origins & evolution of CoGenerate 24:10 Why intergenerational connection matters 27:46 What CoGenerate does to help 31:52 Big policy ideas for the future 37:31 Tips for those nearing retirement 44:15 Upcoming workshop with Chip 48:47 Wisdom bumper sticker 50:51 How does Marc measure success 54:00 Wrapping up Learn more about MEA at ⁠https://www.meawisdom.com/ #MarcFreedman #EncoreCareers #ModernElder #MidlifeReinvention #FindingPurpose #LifeAfterRetirement #GenerationalCollaboration #CrossGenerational #AgingWell #WisdomAtWork #EncoreOrg #CoGenerate #ModernElderAcademy #SecondActCareers #PurposeDrivenLife

Author, speaker, and “Radiant Rebel” Karen Walrond joins Chip Conley for a warm, inspiring conversation on how to age with joy, live on your own terms, and keep your spark alive. From growing up between Trinidad and the U.S., to leaving engineering and law for a creative life, Karen’s story is full of bold choices and unexpected turns. She shares cultural insights on aging, how to break free from the “success script,” and the seven playful experiments from her new book In Defense of Dabbling that prove it’s never too late to try something new. Packed with heart, humor, and practical wisdom, this episode will leave you smiling and inspired to chase your own adventures. Timestamps: 00:00 Intro 00:45 Introduction to Karen Walrond 01:58 Growing up & career journey 06:50 Midlife shift toward writing and creative work 11:38 Cultural perspectives on aging in Trinidad vs. the U.S. 16:55 Defining the “Radiant Rebellion” 19:14 Resisting societal scripts 23:06 Aging in non-white cultures 31:43 Collaboration with Brené Brown 36:12 Introducing In Defense of Dabbling 40:03 The 7 attributes of dabbling 44:08 Why trying new things matters as we age 50:42 Karen’s experience teaching at MEA workshops 53:11 Karen’s wisdom bumper sticker 57:10 Chips’s closing reflections on joy, culture, and lifelong learning Learn more about MEA at ⁠https://www.meawisdom.com/ #AgingBoldly #MidlifeReinvention #RadiantRebellion #LifeOnYourOwnTerms #NeverTooLate #MidlifeTransformation #CuriosityAndPlay #JoyfulAging #BreakingFree #LiveFully #MidlifeMotivation #RedefiningSuccess #KeepYourSparkAlive #IntentionalLiving #TrySomethingNew

What happens when a Harvard scholar, devoted Mormon, and mother of a child with Down syndrome begins to hear psychic messages—and decides to tell the truth no matter the cost? In this powerful conversation, Martha Beck shares how leaving her religion, embracing polyamory, and facing her deepest fears led her to a life of radical integrity, joy, and healing. If you’ve ever felt stuck, out of alignment, or afraid to be fully yourself—this episode will change how you see everything. Timestamps: 00:00 Intro 00:56 Meet Martha Beck 03:02 Growing Up Mormon, Academic Journey, and Her Son’s Diagnosis 10:53 Leaving Mormon Church & Reframing Midlife 14:47 Losing Religion, Finding Soul, and Polyamory 19:20 Returning to True Nature Through Rebellion 21:23 Lessons from Her Son with Down Syndrome 27:10 Psycho-Neuro-Immunology & Integrity 30:58 Shaman Sickness & Becoming a Healer 33:24 A Simple Path to Inner Stillness 40:01 The Radical Power of Not Lying 41:43 How to Listen to Your Body’s Response 52:27 Martha’s Bumper Sticker Wisdom Learn more about MEA at ⁠https://www.meawisdom.com/ #MarthaBeck #ChipConley #TheWayOfIntegrity #MidlifeTransformation #SpiritualAwakening #LeavingMormonism #DownSyndromeParenting #PolyamoryJourney #LifePurpose #InnerHealing #TrustYourself #ModernElder #SelfDiscovery #PsychicExperiences #AnxietyAwareness

What happens when a self-made billionaire steps away from the company she built and faces the big question: What’s next? In this inspiring episode, the founder of Spanx opens up about her journey from door-to-door sales to creating a global brand, the emotional challenges of selling her company, and how she’s redefining success, purpose, and identity in midlife. It’s a raw and uplifting conversation about reinvention, intuition, and finding meaning beyond business. Timestamps: 00:00 Intro 01:56 Family background and kids 03:47 Childhood struggles and early mindset shift 06:32 Discovering Wayne Dyer and self-growth 09:00 Letting go of law school plans 09:46 Intuition and coping mechanisms 13:25 Selling fax machines and rethinking her path 14:17 The idea for Spanx is born 18:40 Building Spanx and landing Neiman Marcus 22:37 Growing Spanx without advertising 25:30 Selling Spanx and facing an identity shift 31:51 Midlife change and grief 34:44 Creating Sneaks brand 43:54 Psychology behind the second venture 47:32 Perimenopause, health issues, and PMDD 50:19 Modern Elder Academy experience 53:37 Focusing on presence and meaning 55:42 Introverts, extroverts, and integration 58:17 Feminine energy as a superpower 59:42 Wisdom bumpersticker 1:02:26 Chip’s final thoughts Learn more about MEA at ⁠https://www.meawisdom.com/ #SarahBlakely #Spanx #FemaleEntrepreneur #WomenInBusiness #EntrepreneurLife #BusinessSuccess #Motivation #Inspiration #FounderStory #StartupJourney #MindsetMatters #SuccessTips #BusinessAdvice #SelfMadeWoman #EntrepreneurMindset #ChipConley #MidlifeChrysalis

What if midlife isn’t a breakdown—but a breakthrough? In this powerful conversation, world-renowned writer Pico Iyer shares the surprising lessons he’s learned from 50 years of friendship with the Dalai Lama, losing everything he owned, and finding stillness in the chaos. From walking away from success in New York to building a soulful life in Japan, Pico reveals how true freedom comes not from having more—but from letting go. This episode is a masterclass in finding purpose, inner peace, and meaning in the second half of life. Timestamps: 00:00 Intro 01:13 Meet Pico Iyer 02:02 Why TED Keeps Inviting Pico Back 02:50 Pico’s favorite TED talk 04:04 Early Life Across Continents 05:17 What “Home” Really Means 07:21 Stillness and the Midlife Chrysalis 12:33 Moving from Park Avenue to Kyoto 15:31 The Value of Being an Expat 18:10 Inner Calm in a Chaotic World 22:31 Everyday Stillness Practices 29:24 A Lifetime with the Dalai Lama 37:34 Living in Absence of Answers 42:29 Pico’s Anticipated Regret 46:11 What Makes MEA So Special 50:47 Awe, Community, and Transformation 53:27 Pico’s Wisdom Bumper Sticker 56:27 Episode Key Takeaways Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeChrysalis #PicoIyer #ChipConley #MidlifeTransformation #ModernElder #Stillness #InnerWisdom #SpiritualGrowth #LifePurpose #DalaiLama #HomeAndSoul #ExpatLife #GratitudePractice #Resilience #MindfulLiving

What happens when a successful actor—and the son of a Hollywood legend—hits midlife and starts asking deeper questions? In this powerful episode, Scott Eastwood opens up about building his own identity beyond Clint Eastwood’s shadow, what 40+ films have taught him, and why he’s now prioritizing purpose over fame. He reflects on masculinity, mentorship, mistakes, and what it really means to grow wiser with age. What happens when a successful actor—and the son of a Hollywood legend—hits midlife and starts asking deeper questions?In this powerful episode, Scott Eastwood opens up about building his own identity beyond Clint Eastwood’s shadow, what 40+ films have taught him, and why he’s now prioritizing purpose over fame. He reflects on masculinity, mentorship, mistakes, and what it really means to grow wiser with age.Feeling your own shift? Subscribe to The Midlife Chrysalis and explore Modern Elder Academy’s workshops designed to help you thrive in midlife and beyond. Timestamps:00:00 Intro00:41 Chip’s Relationship With His Dad 08:28 A Prolific Film Career09:38 Working with Clint Eastwood10:51 Carving His Own Path13:54 New Projects & Genre Exploration15:52 Masculinity in Modern Culture18:09 Growing & Maturing as a Man19:26 Questioning & Redefining Midlife21:32 Childhood Dreams & Creative Shifts24:05 Aging, Directing & Creative Control27:1 Time, Regret & Following Your Gut31:51 The Outpost Movie & Hyperbaric Healing35:07 Real Wellness, Not Wellness Trends37:16 Life Lessons & Emotional Maturity39:44 How Scott Hopes to Be Remembered41:31 Lessons from Mom & Dad43:20 Having Mentors & Becoming One44:13 Scott’s Wisdom Bumper Sticker49:13 Healing a Father-Son Relationship Learn more about MEA at ⁠https://www.meawisdom.com/ #ScottEastwood #MidlifeChrysalis #ChipConley #ClintEastwood #MasculinityToday #ActorLife #FilmIndustry #PersonalGrowth #LegacyAndIdentity #MidlifeReflection #LifeLessons #EmotionalMaturity #CreativeJourney #WellnessWisdom #FollowYourGut

What happens when one of the most thoughtful voices in public life hits a wall? In this deeply personal conversation, Krista Tippett opens up about burnout, walking away from success, and rediscovering joy in midlife. From letting go of exhaustion to falling in love again, she shares the hard-won wisdom that’s reshaping how she lives, works, and loves. It’s a moving reminder that it’s never too late to begin again, so don’t miss this one. Subscribe for more powerful conversations that spark reflection, reinvention, and real change in midlife. Timestamps: 00:00 Welcome and Setup 00:46 Introducing Lee and the Unique Cast of Guests 01:52 What Makes a Great Interviewer? 06:12 Interviewing John O’Donohue 09:57 Thresholds and Transitions 12:58 Krista’s Childhood and Upbringing in Oklahoma 17:40 The Bible as Her First Text of Imagination 20:00 Interviewing Richard Rohr and Men’s Spiritual Lives 23:36 Krista’s Midlife Reflections 27:06 Midlife Chrysalis and Personal Transformation 30:53 Building a Life Around Love and Friendship 35:36 What She’d Regret Not Doing 38:09 What Brings Joy Now 42:03 Defining Wisdom and Growing Wiser 46:26 Staying Grounded Through Rituals and Attention 51:43 Rethinking Retirement 54:29 The Aging Brain and Synthesizing Wisdom 57:46 Wisdom Bumper Sticker Learn more about MEA at ⁠https://www.meawisdom.com/#MidlifeWisdom #OnBeing #KristaTippett #MidlifeTransformation #SpiritualGrowth #LifeAfter40 #InnerLife #FindingPurpose #EmotionalResilience #WomenOver40 #BecomingWise #SoulfulLiving #PersonalGrowthJourney #AgingWithGrace #DeepConversations

What if your so-called “midlife crisis” was actually a doorway to reinvention? In this powerful conversation, Burning Man CEO Marian Goodell joins Chip Conley to explore how the radical spirit of Burning Man offers surprising lessons on aging, identity, leadership, and legacy. From embracing impermanence to finding purpose without a script, this episode is a deep dive into how midlife can be your most creative and meaningful chapter yet. Timestamps: 00:00 Intro 00:40 Chips Connection to Burning Man 04:43 What Burning Man Really Is 07:01 How Burning Man Became a Global Movement 08:47 The Core Principles That Guide Everything 11:13 Radical Self-Expression and Creating Without Expectation 13:38 Why Burning Man Attracts People in Midlife Transition 16:43 Loss, Legacy, and What We Leave Behind 21:46 Lessons from Larry Harvey as a Modern Elder 25:05 What She Learned as a Burning Man’s CEO 33:00 What Is Fly Ranch and Why It Matters 36:28 Fly Ranch Like Burning Man’s Feminine Side 39:24 Three Tips for Burning Man First-Timers 42:14 Burning the Man and Temple Rituals 47:22 The Healing Power of Ritual 50:08 Why MEA Resonates with Burners 53:40 Wisdom Bumper Sticker Learn more about MEA at ⁠https://www.meawisdom.com/ #BurningMan #MidlifeCrisis #MidlifeTransformation #MarianGoodell #BurningMan2025 #PersonalGrowth #ReinventionAfter40 #MidlifeAwakening #LifeAfter50 #SpiritualJourney #BurningManExperience #RadicalSelfExpression #MidlifeChrysalis #ChipConley #PurposeInMidlife

What does it really take to start over at 69? In this inspiring episode, Whole Foods founder John Mackey shares how psychedelics, purpose, and love reshaped his path after selling to Amazon.From ego death to building Love Life wellness centers, he opens up about business regrets, spiritual breakthroughs, and midlife transformation. You'll learn how conscious capitalism evolves with age—and why love might be the ultimate business strategy. Subscribe for more honest conversations about midlife renewal, purpose-driven living, and personal reinvention. Timestamps: 00:00 Intro 00:27 Meet John Mackey 01:27 Psychedelics, Ego Death, and Food as Purpose 07:44 Love, Breakups, and Big Business Shifts 08:37 Austin in the '70s and Building Whole Foods 10:40 Advice to His Younger Self 12:34 From Atheism to Spiritual Adventure 14:36 What Is Conscious Capitalism? 17:15 How Whole Foods Revolutionized Grocery Stores 19:28 Learning to Communicate with Kindness 21:46 Selling Whole Foods to Amazon 28:17 Why He Finally Left Whole Foods 29:25 Healing Journey Through Plant Medicine 31:28 What Is Love Life? 37:56 Psychodelics as Therapeutic Method 40:21 Challenges and Financial Realities 43:21 Longevity Myths and What Actually Works 47:49 Redefining Retirement with Purpose 49:54 What He’d Regret Not Doing 52:09 Wisdom Bumper Sticker 55:33 Final Reflections Learn more about MEA at ⁠https://www.meawisdom.com/ #JohnMackey #WholeFoods #ConsciousCapitalism #MidlifeTransformation #LongevityTips #PlantMedicine #PsychedelicHealing #PurposeDrivenLife #HolisticHealth #LoveLifeWellness #SpiritualGrowth #EntrepreneurMindset #ChipConley #FoundersJourney #ReinventYourself

What if hitting rock bottom was the best thing that ever happened to you? In this raw and inspiring conversation, Rich Roll, a former addict turned world-class endurance athlete, shares how he rebuilt his life from scratch, facing failure, financial ruin, and identity loss to find real purpose. With brutal honesty, he opens up about his addiction, fatherhood, marriage, legacy, and the heavy cost of chasing approval. If you're feeling stuck, burned out, or unsure what comes next, this conversation just might change how you see your own story. Timestamps: 00:00 Introduction 01:13 Spine Surgery and Recovery 03:02 Losing Identity and Facing Stillness 05:47 Interviewing Master Interviewers 07:17 Life Begins at 40 & Rejecting the Race 11:06 How to Know You’re on the Right Track 13:42 Performance vs. Presence 15:25 Addiction, Achievement, and the Roots of Disconnection 19:49 The Midlife Chrysalis at Age 39 24:29 The Support of His Wife Julie 26:04 Lessons from Rich’s Midlife Chrysalis 32:14 From Blog to Writing a Book 38:10 Launching the Podcast & Relocating to Hawaii 42:27 Gaining Momentum 43:50 Financial Struggles and Family Impact 48:14 What Makes Rich Roll’s Podcast Different 51:58 The Importance of Genuine Curiosity 54:25 The Power of Vulnerability in Conversation 56:31 Rethinking Success and Slowing Down 01:01:46 Legacy, Family, and Showing Up Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeTransformation #RichRoll #SpineSurgeryRecovery #SobrietyJourney #PurposeInMidlife #EnduranceAthlete #AddictionRecovery #MidlifeReinvention #PersonalGrowth #PodcastLife #EmotionalResilience #LifeAfter40 #LegacyWork #AuthenticLiving #ModernElder

What if midlife isn’t a crisis, but your most creative chapter yet? In this inspiring and deeply personal episode, bestselling author and entrepreneur Seth Godin shares how he’s reinvented his life through purpose-driven work, disciplined freedom, and the belief that life itself is a series of art projects. We explore why the “dip” is a crucial part of growth, how to walk away from success when it no longer serves you, and what it really means to build a legacy. Seth also opens up about aging, identity, and choosing meaning over momentum. It’s a conversation full of wisdom, honesty, and practical insight for anyone navigating change. Subscribe for more episodes that help you reimagine your next chapter! Timestamps: 00:00 Intro 01:16 How Seth and Chip first met at Stanford 02:49 Writing their first book together 03:53 Jay Conrad Levinson as a modern elder 07:01 Writing over 150 books 08:31 Understanding The Dip and its midlife parallels 12:28 Seth’s two “Dip” examples 14:13 Chip’s hotel dip and decision making 17:27 Creativity, resilience, and entrepreneurship after 50 19:36 Not being in high school anymore & insulating yourself 22:49 Midlife crisis or chrysalis? 27:25 Alt MBA, The Carbon Almanac, and collaborative creation 32:03 Rebranding midlife and self-image as we age 35:28 Things that got better with aging 37:54 Seth’s perspective on retirement & legacy 41:16 Seth’s next project 42:42 The future of the U.S. and generational change 46:28 A bumper sticker of wisdom 48:14 The importance of the origin story Learn more about MEA at https://www.meawisdom.com/ #SethGodinInterview #MidlifeChrysalis #StanfordStories #TheDipBook #PortfolioLife #ModernElderAcademy #CarbonAlmanacProject #AltMBAJourney #RebrandingMidlife #CreativeAging #WisdomInMidlife #OpportunityCostLesson #EntrepreneurAfter50 #LifeAsArtProject #TeachingLegacy

At 40, Hoda Kotb’s world fell apart—cancer, divorce, and the dream of having children slipping away. But what came next wasn’t the end. It was a beginning. In this amazing episode, Hoda opens up about surviving breast cancer, finding the courage to adopt at 52, and learning that her 50s would become the most meaningful years of her life. She shares raw moments, unexpected joy, and the wisdom that only comes from starting over. If you're navigating change or wondering if it's too late to begin again, this episode will speak straight to your heart. Subscribe to Midlife Chrysalis and join our community for more stories that prove the second half of life can be the best half. Timestamps: 00:00 Intro 01:23 Growing Up in an Immigrant Family 03:25 Childhood in Nigeria and Egypt 05:49 Rejection, Resilience, and Unexpected Opportunities 08:27 A Tumultuous Early 40s: Marriage, Cancer & Change 14:14 Aging On-Air and Thriving in Her 50s 17:26 Adoption at 52 and the Joy of Motherhood 23:32 Love & Relationships Later in Life 28:59 Stepping Away from the Today Show 32:51 Starting a New Business at 60 34:39 Gratitude for Her Mom 36:22 Lessons from Her 60s: Be a Beginner Again 41:26 Hoda’s Wisdom Bumper Sticker 44:05 Closing Reflections Learn more about MEA at https://www.meawisdom.com/ #HodaKotb #MidlifeChrysalis #WomenOver50 #BreastCancerSurvivor #MidlifeTransformation #ReinventionAfter50 #AdoptionStory #LifeAfterCancer #StartingOverAt50 #InspirationalWomen #PersonalGrowthJourney #LateBloomerSuccess #CareerChangeAfter50 #FindingPurposeInMidlife #NeverTooLate

What if the life you built is no longer the one that fulfills you? In this powerful episode, former venture capitalist turned CEO coach Jerry Colonna shares how his midlife crisis became a chrysalis—from collapsing under the weight of outward success to rebuilding a life rooted in meaning, connection, and emotional resilience. He shares the moment he almost gave up, the books and mentors that helped him begin again, and why real leadership starts with healing yourself. If you're navigating uncertainty or chasing purpose after 40, this is your roadmap. Subscribe for more conversations that honour the complexity—and beauty—of becoming whole. Timestamps: 00:00 Intro 00:51 Greeting and introduction 02:06 Jerry’s background & career journey 09:36 Fundamentally being broken 12:33 The crash of 2001 and Grand Canyon awakening 15:35 Post-9/11 breakdown and decision to change 18:41 The power of asking “How am I complicit?” 21:41 The pursuit of wealth and inner emptiness 25:57 Childhood trauma and the need to be seen 28:31 The transformation: from ego to true self 33:31 Becoming Buddhist business coach 37:57 Lessons from modern elders: Pema, Parker, Sharon 44:56 What gets better with age 47:10 Midlife wisdom and personal integration 51:34 The ability to enjoy bitter sweetness 52:50 Why do we need midlife wisdom schools 54:37 Collective healing and “you’re not alone” 56:10 Bumper sticker of wisdom Learn more about MEA at https://www.meawisdom.com/ #MidlifeTransformation #JerryColonna #CEOCoach #EmotionalResilience #MidlifeAwakening #MentalHealthMatters #LeadershipWisdom #SpiritualGrowth #BurnoutRecovery #Psychoanalysis #BusinessAndSpirituality #RebootYourLife #ModernElders #LifeAfterSuccess #YoureNotAlone

What if midlife isn’t a crisis—but a chance to grow, heal, and start fresh? In this episode, Michael Franti shares how he transformed personal pain into purpose, why letting go of old stories changed his life, and how music helped him reconnect with himself and others. Michael opens up about fatherhood, breaking free from emotional patterns, and the daily work of staying present in a distracted world. From his earliest songwriting days to his biggest transformations offstage, he reveals what it really takes to live with heart and intention. This episode is full of truth, warmth, and perspective for anyone ready to evolve. Timestamps: 00:00 Intro 01:17 Maturing Through Mistakes 03:07 Impactful Midlife Transitions 06:03 AIDS Crisis & The Power of Sharing Stories 10:40 Success in His 50s & Roll of Wisdom 13:09 Creating from Emotion & Collaboration 18:06 Musical Genres & Identity Challenges 21:09 Learning to Play Guitar at 30 25:55 Moments with Bono and Childhood Trauma 34:16 Emotionally Unavailable Adoptive Mother 39:39 Overcoming Phone Addiction 43:17 Creating Deep Family Relationships 44:55 How His Dad Changed After a Stroke 48:26 Break Up with Everything You Don’t Need 51:47 Live Performance 55:33 Letting Go of Old Stories Learn more about MEA at ⁠MEAWisdom.com #MichaelFranti #MidlifeTransformation #PersonalGrowth #EmotionalHealing #FatherhoodJourney #LettingGo #LiveWithHeart #MindfulLiving #MusicAsMedicine #BreakTheCycle #StorytellingMatters #LifeAfter50 #HealingThroughMusic #IntentionalLiving #PresenceOverPerfection #SpiritualAwakening #NewBeginnings

What if the most powerful transformation of your life came after the titles, the heartbreak, and the noise? In this deeply moving episode, Maria Shriver opens up about rediscovering her identity beyond the Kennedy legacy, confronting the emptiness behind external success, and finally giving herself permission to become whole. From her Catholic upbringing and complicated relationship with ambition, to the raw honesty of her poetry and spiritual healing, Maria shares how she moved through loss, betrayal, and public scrutiny—and came out the other side free, grounded, and fully herself. If you're navigating your own midlife reinvention, craving deeper purpose, or learning to let go of old roles, this conversation will stay with you long after it ends. Timestamps: 00:00 Intro 00:34 Who is Maria Shriver? 02:18 Faith Journey & Early Influence 05:20 Self-Discovery & Wholeness 07:44 Poetry & Embracing a Feminine Side 09:40 Finding Out Who You Really Are 15:06 The Poem “Connecting the Dots” 19:27 Messy Midlife & Reframing Aging 22:11 The Poem “Chaos” & Coming Out of Mess 30:14 Redefining Purpose, Love, and Legacy 32:21 Vulnerability as a Superpower 38:21 Embracing Freedom & Your True Self 41:05 Living Fully on Your Own Terms 44:48 What is Moral Beauty? 47:57 Evolving & Aging as a Gift 56:20 Final Wisdom Learn more about MEA at MEAWisdom.com #MariaShriver #MidlifeTransformation #Reinvention #SpiritualGrowth #FindingYourself #WomenEmpowerment #HealingJourney #EmotionalHealing #LettingGo #PoetryHealing #LegacyBeyondFame #VulnerabilityIsStrength #RedefiningSuccess #MoralBeauty #PersonalGrowth

Welcome to the very first episode of The Midlife Chrysalis! Chip Conley kicks off this amazing podcast by redefining midlife. It’s not as a crisis, but a powerful chrysalis for transformation. He shares his own wild journey and reveals why your 40s, 50s, and beyond can be the most meaningful years of your life. Plus, get a sneak peek at upcoming guests like Maria Shriver, Brian Chesky, Gavin Newsom, and more. If you're ready to reinvent yourself and thrive in midlife, this is your new go-to podcast. Timestamps: 00:00 Welcome to The Midlife Chrysalis 00:40 My Journey from Crisis to Chrysalis 01:24 Midlife as Time of Major Transition 02:15 Why This Podcast Matters 02:24 Upcoming Guests 03:08 An Invitation to Join the Journey Learn more about MEA at ⁠MEAWisdom.com #MidlifeTransformation #ReinventYourLife #ModernElder #MidlifeJourney #AgingWithPurpose #MidlifeMotivation #LifeAfter40 #LifeAfter50 #SecondActSuccess #MidlifeReinvention #PurposefulLiving #LongevityMindset #ChipConley #UCurveOfHappiness #MidlifeWisdom