The Midlife Chrysalis

Chip Conley
  • 5.0 (44)
  • 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. 1D AGO

    Why Transitions Break Us and Heal Us | Kari Cardinale

    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

    51 min

  2. 4D AGO

    From Skateboarding Icon to Modern Elder: Stacy Peralta

    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

    50 min

  3. 6D AGO

    The Success Treadmill Is Real: Here’s How to Escape

    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

    21 min

  4. DEC 22

    The Hidden Cost of Playing It Safe in Midlife | Dr. Margie Warrell

    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

    52 min

  5. DEC 19

    ​​Why Dating Feels Hard in Midlife (Even for Smart People) | Rachel Greenwald

    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

    57 min

  6. DEC 17

    Inside the Messy Middle: What Actually Drives Transformation in Midlife

    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

    23 min

  7. DEC 15

    Michael Clinton on Life Layering: How to Build a Richer Life After 50

    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

    1h 2m

  8. DEC 12

    Laird Hamilton & Gabby Reece on Love, Longevity, and Aging with Power

    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

    59 min
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5
out of 5
44 Ratings

About

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

Information

  • Creator
    Chip Conley
  • Years Active
    2K
  • Episodes
    49
  • Rating
    Clean
  • Copyright
    © Chip Conley
  • Show Website
    The Midlife Chrysalis

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