The Midlife Chrysalis

Chip Conley
  • 0.0 (0)
  • SELF-IMPROVEMENT
  • UPDATED WEEKLY

The Midlife Chrysalis is a one-hour podcast hosted by Chip Conley, bestselling author of Learning to Love Midlife and founder of MEA (Modern Elder Academy). Chip and his high-profile guests – including Maria Shriver, Hoda Kotb, Elizabeth Gilbert, Michael Franti, and more – dive into raw, vulnerable conversations about the profound transitions they’ve experienced in midlife. Listeners get a rare look at how even the most successful individuals have to navigate life’s pivotal changes – and gain practical wisdom they can apply in their own lives for a more fulfilling and purposeful next chapter.

  1. 1 DAY AGO

    Why Facing Mortality Changes How You Live | Dr. Kerry Burnight

    In this episode, I sit down with gerontologist Kerry Burnight, who has spent decades working with people in their 80s, 90s, and even 100s. And what she’s learned might completely change how you think about aging, and how you choose to live right now. Kerry introduces a powerful idea called joyspan, the missing piece between how long you live and how well you live. And the truth is, most people are getting this wrong. Here are a few insights that stayed with me: Joy isn’t the same as happiness. It’s something you build from the insideThe closer we get to the end, the clearer it becomes what actually mattersPeople don’t regret not achieving more, they regret not loving moreEven in the hardest moments, joy is still available to usYou always have something to give, no matter your age or stage of life This is one of those conversations that makes you pause, reflect, and maybe rethink how you’re living your life. Watch now. Timestamps: (02:58) From chance meeting to life impact (08:04) Difference between joy and happiness (11:34) Lifespan vs. healthspan vs. joyspan (13:03) Joyspan as a skill you can build (16:52) Finding joy while facing illness (19:48) Viktor Frankl and meaning in suffering (24:18) What older people teach us about life (28:35) Why aging can make you whole (30:37) The hidden danger of internalized ageism (35:00) What really matters at the end of life (37:09) The midlife anxiety turning point (41:01) Midlife unraveling and becoming yourself (44:01) Inside the joyspan retreat experience (46:25) Why this matters at any age (48:12) The one life lesson that changes everything Learn more about MEA at ⁠https://www.meawisdom.com/ #joyspan #agingwell #gerontology #longevity #healthspan #midlifetransformation #meaningoflife #deathanddying #endoflife #elderwisdom #lifelessons #purposefulliving #emotionalwellbeing #innergrowth #modernelder

    50 min

  2. 3 DAYS AGO

    What Keeps You Together When Everything Falls Apart?

    What happens when life changes all at once? In this deeply emotional conversation, Chip opens up about one of the hardest seasons of his life: facing stage 3 cancer again while grieving the loss of his mother, navigating relationship changes, caring for his aging father, and trying to hold onto purpose through it all. But this episode isn’t about giving up. It’s about what keeps us going when life feels unbearably heavy. You’ll hear: What it feels like to face mortality head-onWhy Chip stopped hiding his struggles from the worldThe unexpected power of purpose, community, and honest conversationHow grief, fear, and uncertainty can reshape a lifeWhy staying open during hard times may be the real path to wisdom This is one of the most vulnerable conversations we’ve ever shared, honest, human, heartbreaking, and deeply hopeful at the same time. Listen now and share it with someone who might need to hear these words today. Timestamps: (00:46) Welcome to Wisdom Wednesday (02:20) Why Chip Chose Baja California (04:18) The Culinary Scene in Todos Santos (06:21) Summer Refresh at MEA (08:32) Chip Opens Up About His Life Quake (11:38) What Transitional Intelligence Means (13:45) Purpose, Calling, and Cancer (14:42) The Reality of Hormone Depletion Therapy (15:35) What Changed Since Chip’s First Diagnosis (19:57) What Chip Learned from Cancer Workshops (23:45) Living Through Hard Times Publicly (28:01) Why Chip Rejects the “Perfect Guru” Persona (32:19) The Biggest Predictors of Longevity Learn more about MEA at ⁠https://www.meawisdom.com/ #CancerJourney #GriefAndHealing #MidlifeWisdom #PersonalGrowth #EmotionalHealing #LifeTransitions #MentalHealthAwareness #PurposeDrivenLife #Mortality #Resilience #HealingJourney #SelfDevelopment #Longevity #WisdomWednesday #LifeAfterLoss

    30 min

  3. 5 DAYS AGO

    Feeling Stuck at 50: How to Find Your Magic and Start Again | Matt Ross

    The moment everything starts falling apart might be the moment your life finally comes together. In this episode, Chip Conley sits down with entrepreneur and author of Grow or Fold, Matt Ross, to explore a powerful story of midlife reinvention. From a high-pressure career in radio to building purpose-driven businesses, Matt shares how personal crisis, burnout, and uncertainty became the catalyst for real change. Here’s what you’ll take away: Why feeling “stuck” at 50 is often the start of something betterThe simple mindset shift that turns breakdown into breakthroughHow to treat your life like a business—and actually redesign itWhat it really means to “find your magic” (and how to do it)Why growth, not comfort, is the key to a fulfilling second half of life If you’re at a crossroads, questioning what’s next, or just know there’s more out there for you—this conversation will hit home. Watch now and take the first step toward your next chapter. Timestamps: (00:00) Intro (05:00) Breaking into CBS and early career growth (08:24) Turning around a failing radio station (11:16) Music strategy and audience targeting (13:57) Leaving radio and industry decline (15:35) Joining School of Rock as CEO (18:15) Launching One River School at 50 (22:18) Writing Grow or Fold and personal crisis (26:06) Treating life like a business (29:52) Personal struggles and rebuilding (30:15) Vision planning and long-term goals (33:15) Lessons from age 50 to 65 (37:42) Grow vs fold mindset (41:46) Midlife purpose and transformation (45:54) Entrepreneurship and self-awareness (47:54) Final life lesson and philosophy Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeCrisis #LifeAfter50 #PersonalGrowth #ReinventYourself #FindYourPurpose #SelfAwareness #MidlifeTransformation #CareerChange #PersonalDevelopment #MindsetShift #StartAgain #LifeRedesign #GrowthMindset #EntrepreneurMindset #PurposeDrivenLife

    54 min

  4. 8 MAY

    What Horses, Death, and Nature Taught Me About Being Human | Kelly Wendorf

    What if the life you built… no longer feels like yours? In this powerful episode, Kelly Wendorf joins Chip Conley for a raw conversation about loss, identity, and the moment everything shifts. From caring for a dying parent to rediscovering yourself through nature, this episode goes straight to the heart of what it means to truly live. Here’s what you’ll take away: Why success can still leave you feeling emptyHow facing death reshapes how you see lifeWhat “rewilding” really means and why it mattersHow nature (and horses) reflect who you really are If you’re going through a big shift, dealing with loss, or just feeling like something’s off—this one will really hit. 👉 Watch the full episode now. Timestamps: (05:13) Kelly’s early life (06:52) Archaeological sites and sacred Kivas (09:35) A warrior who redefined masculinity (14:35) Challenges of depth and relationships (21:06) Growing older and becoming whole (23:14) Story of Kelly’s mother and final months (36:29) What rewilding means (40:15) Why nature helps transformation (43:54) Lessons from horses (49:12) Final wisdom and life lesson (53:38) Closing thoughts and gift for listeners Learn more about MEA at ⁠https://www.meawisdom.com/ Free Workshop Gift from Our Guest Join the Transformative Life Workshop for free: https://www.theequusacademy.org/courses/how-to-lead-a-transformative-life-2026 Use code: Equus100kw #CaringForADyingParent #FacingDeath #LifeAfterLoss #RewildingLife #MidlifeAwakening #GriefAndGrowth #EndOfLifeCare #IdentityShift #FindingYourselfAgain #EmotionalHealingJourney #LettingGo #MeaningAfterLoss #NatureHealing #HorseWisdom #DeepConversations

    51 min

  5. 6 MAY

    AI vs Humans: The One Skill AI Still Can’t Replace

    AI is changing work faster than anyone expected… but most people are focusing on the wrong thing. In this episode, Chip Conley and Derek Gehl break down what AI actually means for your career, especially if you're in midlife and wondering where you fit in. Here’s what matters: AI is replacing routine work first, not higher-level thinkingWisdom now matters more than knowledge in an AI-driven worldOver-relying on AI can weaken your own skillsCuriosity and adaptability are your biggest advantages This isn’t about fear. Ot’s about knowing where you stand and how to move forward. 👉 Listen now to learn how to stay relevant and think for yourself in the age of AI. Timestamps: (00:00) AI and human wisdom (01:20) How AI frees mental bandwidth (02:30) Who is most vulnerable to AI (04:00) Knowledge vs wisdom (06:39) AI adoption inside organizations (07:44) Fear and resistance to AI (09:21) Scaling with AI and team adoption (10:52) How to stay relevant in the AI era (11:41) Best AI tools to start with (12:57) Learning AI through curiosity (15:07) Don’t lose core skills to AI (16:45) Practical steps to start using AI Learn more about MEA at ⁠https://www.meawisdom.com/ #AI #ArtificialIntelligence #FutureOfWork #AIJobs #CareerGrowth #StayRelevant #WorkTrends #DigitalTransformation #AIFuture #HumanSkills #Wisdom #CareerAdvice #MidlifeCareer #AIAwareness #FutureSkills

    17 min

  6. 4 MAY

    The New Way Women Over 50 Are Choosing to Live | Elizabeth White

    In this powerful conversation, Elizabeth White, author of 55, Underemployed, and Faking Normal, shares how losing everything during the recession led her to uncover a hidden crisis affecting millions of women over 50… and a bold new solution. Here’s what you’ll learn: Why financially stable women are quietly slipping into insecurityWhy housing, not healthcare, is the real pressure point in midlifeHow “Golden Girls”–style co-living is becoming a practical path forwardWhat most people get wrong about shared living, and how to know if you’re readyWhy the “wisdom worker” era could redefine aging as an advantage This episode reframes what it means to grow older and how to do it with more connection, security, and intention. Don’t Call Them Retirement Communities: https://www.nytimes.com/2026/03/30/realestate/modern-elder-academy-adult-co-living-retirement.html?smid=nytcore-ios-share 🎧 Listen now and rethink your future. Timestamps: (00:00) Intro (00:46) Meet Elizabeth White (01:29) Job loss and midlife crisis (05:41) Book and growing audience (08:49) Advice for financial survival (10:29) Using support systems (12:55) Resilience circles explained (15:35) Path to co-living idea (18:00) Housing as main challenge (19:40) Golden Girls housing concept (22:11) Growing interest in co-living (23:23) Demand vs developer gap (26:41) Retreat insights and readiness (29:04) Are you ready for co-living (31:20) Types of shared housing (32:49) Future of co-living in America (34:11) Housing crisis and aging (37:22) Economic challenges and solutions (39:44) Fear of financial insecurity (40:38) Wisdom worker era (41:21) Life lessons and aging well (43:36) Redefining luxury (45:09) Challenging age limitations Learn more about MEA at ⁠https://www.meawisdom.com/ #WomenOver50 #MidlifeLiving #CoLiving #SharedHousing #GoldenGirlsLiving #LifeAfter50 #AgingWell #MidlifeReset #HousingCrisis #SoloAging #Over50Lifestyle #CommunityLiving #RetirementPlanning #WomenSupportingWomen #ModernAging

    55 min

  7. 1 MAY

    You Were Never Meant to Think This Way | Angus Fletcher

    In this episode, Angus Fletcher, a professor, author, and advisor to U.S. Army Special Operations, explains why so many people feel stuck even when life looks “right,” and what important human abilities we slowly lose as we get older without noticing. Instead of chasing more knowledge, Angus points to a different path, one built on the natural abilities we all had as children but were slowly trained out of as we grew up. Here’s what you’ll take away: Why AI can’t replicate human thinking and what it gets completely wrongThe 4 core human abilities most adults lose over timeHow to rebuild intuition and creativity in simple, real waysWhy struggle is essential for growth, not something to avoidThe shift that turns midlife from feeling stuck into a meaningful transition This conversation doesn’t just explain the problem. It gives you a new way to see your life, your story, and what’s still possible. 🎧 Watch now and reconnect with the part of you that’s been missing. Timestamps: (02:48) Meet Angus Fletcher (03:39) Background and early life (05:50) Books and primal intelligence explained (06:49) Limits of AI vs human intelligence (08:36) Redefining intuition and emotion (10:05) What is primal intelligence (11:31) AI myths and general intelligence (13:29) Why AI can’t innovate like humans (14:33) Wisdom vs intuition (16:07) How to develop intuition (18:07) Conversations and curiosity exercise (20:36) Story thinking and human cognition (22:48) Rewriting your life story (26:53) Storytelling for leaders (27:43) Transition struggle and antifragility (30:39) Wonder vs curiosity vs awe (32:58) Building a sense of wonder (36:50) Personal midlife challenges and marriage (40:55) The future of AI and human connection (43:17) Life advice and no hero like you (44:36) Teaching and lifelong learning Learn more about MEA at ⁠https://www.meawisdom.com/ #PrimalIntelligence #HumanSkills #Intuition #Imagination #EmotionalIntelligence #StopOverthinking #MindsetShift #PersonalGrowth #MidlifeGrowth #FindYourself #HumanVsAI #ThinkingSkills #InnerGrowth #LifePurpose #SelfDiscovery

    48 min

  8. 29 APR

    Why Success Stops Making You Happy After 40

    You checked all the boxes… so why does something still feel off? In this episode, Chip Conley and Derek Gehl explore what happens when success stops feeling like success, and why so many people hit this wall in midlife. And what you can do when you get there. Here’s what you’ll learn: The 3 questions that reveal your true directionWhy achievement alone doesn’t lead to fulfillmentThe hidden trap of defining success through workWhy relationships matter more than you thinkHow to start redefining success in a way that actually feels good If you’ve ever caught yourself thinking “is this really it?”, you’re not the only one. 👉 Watch the full episode and rethink what success really means Timestamps: (01:53) MEA & Arthur Brooks collaboration (06:38) Three questions of The Meaning of Your Life (10:05) From success to significance (11:26) How society defines success today (16:23) Evolution of success through history (18:08) Happiness rankings and cultural differences (20:11) Why midlife triggers change (22:23) Practical exercise to redefine success (24:38) Where people find the most meaning Learn more about MEA at ⁠https://www.meawisdom.com/ #midlifecrisis #personalgrowth #findyourpurpose #successmindset #lifepurpose #selfdiscovery #meaningoflife #highachievers #midlifetransformation #innerfulfillment #successvsmeaning #mentalwellbeing #lifeafter40 #selfreflection #purposefullife

    25 min
See All (108)

Trailer

About

The Midlife Chrysalis is a one-hour podcast hosted by Chip Conley, bestselling author of Learning to Love Midlife and founder of MEA (Modern Elder Academy). Chip and his high-profile guests – including Maria Shriver, Hoda Kotb, Elizabeth Gilbert, Michael Franti, and more – dive into raw, vulnerable conversations about the profound transitions they’ve experienced in midlife. Listeners get a rare look at how even the most successful individuals have to navigate life’s pivotal changes – and gain practical wisdom they can apply in their own lives for a more fulfilling and purposeful next chapter.

Information

  • Creator
    Chip Conley
  • Years Active
    2025 - 2026
  • Episodes
    108
  • Rating
    Explicit
  • Copyright
    © Chip Conley
  • Show Website
    The Midlife Chrysalis

You Might Also Like