The Midlife Chrysalis

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 liveThis 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 philosophy05:28 Philosophy and physics connection07:03 Why write about midlife10:15 What defines midlife12:46 Pressures, regret, and time poverty15:27 Telic and atelic activities20:03 Intrinsic and extrinsic motivation21:23 Flow and engagement22:37 Finding atelic activities25:24 Chronos and Kairos30:00 Anticipated regret as wisdom34:48 Choosing a personal philosophy37:38 Philosophers Kieran admires40:47 When midlife ends43:42 Philosophy and young people48:19 Philosopher as president51:03 Making philosophy practical53:26 A life philosophy bumper sticker57:37 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 achievementThis 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 setup00:42 Episode introduction01:00 Workshops and unexpected contrasts03:12 Ricky Williams and walking away from football04:28 Cancer scans and living with uncertainty05:20 Death as a daily presence06:00 Prostate cancer diagnosis and treatment journey10:43 Hormone therapy and energy loss13:46 Feeling mortality in the body14:16 Memento mori and midlife urgency16:30 Legacy and ripple of impact18:24 Near death experience story22:47 Succession planning and leadership wisdom23:18 Talking about death without fear26:10 Purpose usefulness and meaning28:20 Wisdom bumper sticker on mortality30:04 Gratitude and closing reflectionsLearn 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 AIThe 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 journeys18:36 What Your Brain on Art is really about21:25 Neuroaesthetics and brain science23:54 Why creativity is essential for health24:24 How to rebuild creativity in midlife29:14 Art, neuroplasticity, and medicine34:32 Creativity inside Google39:18 Digital literacy, nature, and balance41:35 Personal midlife transformation stories45:30 Resilience through illness and change49:08 Life wisdom and defining moments55:51 Final reflections and closingLearn 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 friendships00:45 Friendship as a practice02:10 Reconnecting with old friends04:20 Outgrowing conversations not people06:00 Depth vulnerability and the three vaults09:40 Why friendship requires depth10:48 Men opening up emotionally13:05 Leading with vulnerability13:58 Creating deeper conversations naturally15:48 Different levels of friendship16:39 Couples growth and shared language17:37 Transactional vs real friends18:02 How to rebuild friendships in midlife20:13 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 Introduction00:24 Early Life & Family Loss02:38 Working for Harvey Weinstein05:03 From Film to Entrepreneurship08:15 Lessons on Curiosity & Reinvention10:53 Identity Crisis at 4013:29 Entering the Insurance Industry15:16 Building a PBS Show16:57 Struggling with Identity22:20 Tipping Point at 4724:33 Creating Midlife Male26:30 Marriage Problems & Masculinity30:34 Why He Built Midlife Male38:48 The Modern Midlife Male Dilemma41:37 Conviction, Curiosity & Courage to Speak45:00 The Six F’s of Life & Finding Success49:06 Raising Sons Today54:56 Wisdom Bumper Sticker57:07 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 belongingIf 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 upbringing05:02 Growing up in Venezuela and reflections on the country06:38 Leaving the Bay Area and the midlife turning point09:56 Comparison culture and pressure in the Bay Area11:02 Transactional vs relational relationships12:39 Friendship as a practice15:44 Core lessons on listening and asking better questions18:49 Going first and the mindset of friendship22:14 Friendship health longevity and happiness24:23 Resistance to wellness and personal growth28:44 Self-awareness pattern recognition and wisdom31:46 Midlife transitions and choosing a second adulthood38:10 Midlife crisis vs midlife chrysalis40:29 MEA as a call to action43:55 Creating community and the origins of Baja Sage45:09 Community vs real estate development51:23 Social architecture and relational living52:32 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 midlife04:16 Digital natives vs digital immigrants05:11 The respect gap in mentorship06:20 Defining wisdom and lived experience07:10 Four stages of becoming a modern elder08:22 Appreciative inquiry and powerful questions10:30 Librarian mentor vs confidant mentor12:20 Chip Conley and Herb Kelleher mentorship story14:20 How confidant mentorship builds confidence15:45 How to structure a healthy mentorship16:53 Mentors vs coaches explained18:35 The mentorship gap and retention impact18:51 How to start mentoring at midlife20:55 Mentorship and renewed purpose21:51 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 Chrysalis04:59 Writing with humility and vulnerability07:02 Book titles and framing ideas08:34 Geography of Bliss origin story12:31 Favorite places and soul place13:54 Ben Franklin and usefulness18:31 Writing about God and belief21:44 Geography of Genius and creativity23:30 Introducing The Socrates Express24:10 Knowledge vs wisdom27:23 What philosophy really is30:38 Wonder vs curiosity34:40 Stoicism and modern relevance37:33 Philosophers that resonated most40:53 Thoreau and learning how to see44:52 Why philosophy matters in midlife49:20 Wisdom bumper stickers52:26 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 Intro01:17  Meet Aithan Shapira04:05 Living Between Worlds05:32 MIT, NASA & Global Clients06:32 Practice as a Core Principle07:46 Cubism & Midlife Transition11:00 Life as a Practice vs Routine14:05 Practice vs. Ritual15:30 Aithan’s Views on Midlife20:55 Accelerating Internal Change25:37 The Three Stages of Transition27:59 Coping With Freefall32:59 What Needs to Be Preserved36:11 Identity in Retirement & Second Half of Life38:18 Aithan’s Own Chrysalis Story46:21 Long Life Learning53:21 The Wisdom of Midlife55:58 Aithan’s Bumper Sticker Wisdom59:07 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 journey03:10 Rethinking age and career length05:23 Retirement vs staying relevant10:43 Taking small iterative steps13:25 Entrepreneurship after 5016:33 Bridge jobs and testing ideas18:26 A real midlife pivot story19:18 Purpose, community and wellness23:29 Identity fear and becoming a beginner27:17 Why people come to MEA31:47 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 journey03:50 Panic attack on live TV05:31 From panic attack to meditation06:46 Family background and anxiety08:31 Decade between crisis and mindfulness advocacy09:33 Therapy spirituality and discovering meditation13:37 Writing 10% Happier14:22 Origin of the 10% happier idea16:43 Science and benefits of meditation19:47 Skepticism identity and cognitive dissonance22:14 Life after the book’s success26:06 Productivity versus presence29:47 Burnout hyper productivity and 360 review33:06 Letting go of roles and redefining life35:59 Midlife as chrysalis not crisis39:36 Favorite meditation practices42:09 Wisdom midlife and modern elderhood45:08 Character skills in the age of AI47:07 Personal wisdom and life lessons49:10 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 strengthWatch 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 caregivers06:47 Identity loss and existential impact of cancer07:53 Chip’s cancer diagnosis and early denial13:13 Regret fear, and emotional processing16:23 Cancer as a teacher and life priorities19:39 Anxiety treatment and living with uncertainty20:33 Staying busy to avoid difficult emotions24:16 Values family and vulnerability26:01 Strength identity and emotional suppression28:01 Caregivers and lack of support systems30:10 Invisible burden of caregiving32:06 Emotional catharsis and healing journey35:32 Caregiver and survivor archetypes38:49 Inside the cancer thrivers workshop42:18 Identity mapping and letting go43:41 Meaning values and intentional living45:42 How friends can best support someone with cancer47:26 Cancer is not a linear journey48:28 Wisdom bumper sticker advice51:53 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 routines02:28 Routine vs ritual04:00 Shower meditation prayers05:48 Affirmations and new stretching ritual11:21 The impact of morning rituals12:27 Accountability and consistency14:01 Rituals as landmarks and micro rituals15:24 How to create your own rituals17:07 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 background06:55 Leaving Colorado for Baja08:49 First experience of Baja and Pescadero10:59 Freedom and living in rhythm with nature15:15 Experience design and creating meaningful gatherings17:48 Baking bread as ritual and collective practice22:14 Origin story of MEA24:02 Early doubts and building a local economy26:07 Lessons from the first MEA beta cohorts30:38 Ski towns, purpose, and longevity research33:46 Aging, vitality, and midlife perspective40:49 Introversion, ritual, and reclaiming time46:19 Third vault conversations and authentic community48:26 Moral beauty as a pathway to awe54:11 Transformation through deep connection56:19 Designing belonging and social bonds57:28 Wisdom bumper stickerLearn 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 background04:17 From clinical psychology to coaching07:06 How coaching has developed09:31 Life Forward and Hudson Institute11:46 The midlife happiness curve14:53 Cancer as a life teacher16:06 Hudson Institute and MEA connection18:08 Letting go of old identities21:50 Navigating major life transitions26:27 Why experimentation matters27:39 Men vs women in midlife31:01 What makes a great coach33:47 Why people choose coaching35:15 Gender balance in coaching35:51 Coaching in the age of AI38:20 How to choose the right coach40:38 Creativity later in life42:41 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 Idea04:40 The U Curve of Happiness06:21 Why Midlife Is Not a Crisis09:12 Becoming a Modern Elder11:24 Chip’s Midlife Struggles21:11 Why Midlife Lacks Support Systems23:17 Biology vs Life Circumstances25:49 How to Move from Crisis to Chrysalis30:23 Watching People Self-Destruct in Midlife34:18 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 Chrysalis04:06 Long friendship and early mentorship05:54 Childhood and family background08:48 Gavin’s writing experience16:03 Becoming mayor of San Francisco17:38 Decision to legalize gay marriage25:11 Impact of marriage equality27:54 Political winter as lieutenant governor29:24 Identity loss and slowing down33:21 Humility and leadership lessons35:22 Grace humility after years of division38:46 The lost art of civil disagreement41:49 Political vision and building bridges44:10 Stoicism and wisdom traditions47:44 Fatherhood and authenticity49:27 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 journey02:49 Reality Central and first major failure04:59 The business lesson that shaped TOMS07:49 Creating the one for one model08:43 Selling TOMS and losing identity12:36 Depression behind the public image16:23 Searching for relief outside himself17:24 Medication fog and deep isolation19:30 Why telling others saved his life20:54 Moving beyond traditional medication21:12 Ketamine and TMS25:53 Discovering the core wound28:49 India and lasting inner freedom33:27 Launching the Enough initiative35:58 I’m Enough ritual poem37:57 How the nonprofit model works38:47 The growing mental health crisis43:13 Self compassion and flow state46:28 How to support someone in depression51:54 Living with fear of relapse54:17 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 practiceThis 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 concept03:41 Gray divorce and solo agers06:20 Loneliness and housing mismatch08:05 Why Golden Girls homes now10:10 The Santa Fe pilot homes12:49 Workshops and community vision15:29 What the research revealed18:14 Matching roommates and house culture21:10 Affordability and rental model24:10 What about men26:36 Long term vision and legacy29:21 How to get involved29:55 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