The Midlife Chrysalis

Chip Conley
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  • Self-Improvement
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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. 17 hr ago

    The Truth About Becoming Miserably Successful | Debjani Biswas

    What happens when you do everything “right” in life… and still end up unhappy? In this powerful conversation, I’m joined by Debjani Biswas, leadership coach, bestselling author, and TEDx speaker, to talk about burnout, reinvention, identity, and what it really means to live authentically. She shares her journey from turning down Harvard twice and breaking barriers as the only woman in her IIT engineering class to experiencing a complete midlife unraveling that changed everything. Together with Chip Conley, she explores: Why so many successful people feel empty insideHow fear and perfectionism quietly shape our livesThe surprising freedom that can come from a midlife crisisThe leadership qualities that matter most todayThe simple coaching question that can transform your thinking Warm, honest, and deeply insightful, this episode is for anyone navigating reinvention, purpose, or the pressure to keep it all together. Watch now and discover why your most meaningful chapter may still be ahead. Watch Debjani’s TEDx Talk here: TEDx Talk on Gender Bias and Identity Timestamps: (10:44) Turning Down Harvard Twice (13:19) Being the Only Woman at IIT (16:29) Discovering Executive Coaching (18:47) Indra Nooyi and Women in Leadership (20:38) Midlife Chrysalis at 49 and the First Book (24:32) Breaking Out of Set Path (28:18) Letting Go and Embracing Growth (30:15) The Meaning of Miserably Successful (33:45) The Stress Framework Explained (37:52) Powerful Coaching Questions (40:43) The Leadership Qualities That Matter Most (45:37) How Wisdom Changed Her Life (51:11) Wisdom Bumper Sticker Learn more about MEA at ⁠https://www.meawisdom.com/ #DebjaniBiswas #ChipConley #MidlifeChrysalis #MiserablySuccessful #MidlifeTransformation #ExecutiveCoaching #WomenInLeadership #EmotionalIntelligence #CareerReinvention #LeadershipWisdom #PersonalGrowth #MidlifeReset #FearAndSuccess #PurposeDrivenLife #LeadershipPodcast

    50 min

  2. 2 days ago

    The Millennial Midlife Crisis Won't Look Like You Think

    Are Millennials heading for a midlife crisis or redefining midlife altogether? In this Wisdom Wednesday episode, Chip Conley joins Derek Gehl to explore how millennials are entering midlife differently than previous generations. After growing up through economic uncertainty, social change, and shifting life expectations, many millennials may be approaching midlife with a completely different mindset than their parents. They discuss: Why millennials may never experience a traditional midlife crisisHow the U-curve of happiness is changing for younger generationsWhy millennials are shifting from freedom-seeking to stability-seekingHow longer lifespans are reshaping the concept of midlifeWhy durable skills and wisdom matter more than ever in the age of AI Feeling behind in life? You might be measuring yourself against the wrong timeline. Listen now to discover why the traditional midlife crisis may not apply to millennials and what that reveals about the future of aging, purpose, and fulfillment. Timestamps: (00:00) Millennials Entering Midlife (02:24) The Millennial Midlife Crisis (03:37) The U-Curve of Happiness Explained (04:35) Why Millennials Took a Different Path (06:00) From Midlife Crisis to Constant Reinvention (08:17) The Impact of Longevity on Midlife (09:45) Why Midlife Is Getting Longer (10:25) Will the Happiness Dip Happen Later? (11:38) Living Your Own Life vs Someone Else’s (13:08) Redefining Success for Millennials (14:12) Experiences Over Possessions (15:40) How Millennials Spend Their Money (16:43) What Makes Millennials Different (17:39) Social Media and the Comparison Trap (18:36) The Pressure of Billionaire Success Stories (19:36) Why Millennials Want Systemic Change (20:45) The Future of Younger Generations (21:13) Advice for Millennials Feeling Behind (22:01) Durable Skills in the Age of AI (23:05) Vibe Coding and Final Thoughts Learn more about MEA at ⁠https://www.meawisdom.com/ #Millennials #MidlifeCrisis #MillennialMidlife #Midlife #ChipConley #MidlifeChrysalis #HappinessCurve #MillennialLife #Turning40 #LifeTransitions #ModernElderAcademy #Longevity #PurposeInLife #MillennialSuccess #SelfDevelopment

    22 min

  3. 4 days ago

    The Decade Game That Can Transform Your Future | Carolyn Buck Luce

    Many people reach midlife feeling successful on paper but disconnected from themselves. In this conversation, Chip Conley talks with Carolyn Buck Luce about what it actually looks like to rebuild your life in your 40s, 50s, 60s, and beyond. Carolyn opens up about leaving Wall Street, going through a very public personal crisis, redefining ambition, and creating the “Decade Game”, a simple but powerful way to think about who you want to become over the next 10 years. They talk about: Why purpose often starts showing up earlier than we realizeWhat happens when you stop compartmentalizing your lifeWhy many women feel more confident and free in midlifeHow imagining your future self changes your decisions todayThe difference between wishful thinking and thoughtful wishing This is one of those conversations that feels honest, grounding, and surprisingly energizing, especially if you’ve been feeling the pull toward a new chapter. Watch now and think about the person you want to become next. Timestamps: (05:47) Purpose, Imagination, and Identity (09:19) The Origin of the Decade Game (11:24) Success, Secrets, and Reinvention (16:25) Carolyn’s “Egyptian Period” (18:20) How to Design Your Next Decade (20:01) Reinventing Life After Retirement (23:57) Why Life Changes in Stages (26:36) The Fear of Starting Over (29:46) Why Midlife Can Empower Women (35:12) The Power of MEA and Community (41:40) Rules for Living an Epic Life (43:16) Thoughtful Wishing vs Wishful Thinking Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeChrysalis #ChipConley #CarolynBuckLuce #MidlifeTransformation #PersonalGrowth #WomenOver50 #PurposeInLife #Reinvention #SelfDiscovery #HealthyAging #MidlifeWomen #LifeTransitions #MindsetShift #EmotionalWellbeing #PersonalDevelopment

    41 min

  4. 29 May

    What 88 Years of Research Revealed About Happiness | Robert Waldinger

    For nearly 90 years, researchers tracked one question: what actually makes people happy, healthy, and fulfilled as they grow older? In this episode, Chip sits down with psychiatrist, Zen teacher, and Harvard study director Robert Waldinger to explore what 88 years of research can teach us about relationships, aging, purpose, and emotional well-being. Together, they unpack: Why strong relationships predict happiness and longevity better than success or moneyThe hidden loneliness behind social media and “curated lives”What Zen practice teaches about anxiety, suffering, and being fully presentWhy nobody is happy all the time and why that’s normalHow paying attention to what energizes you can change your life Warm, wise, and deeply human, this episode is full of insights that stay with you long after the conversation ends. Listen now and join the conversation. Timestamps: (03:03) How Life Changed After 50 (06:13) The Harvard Study on Happiness (08:36) Why Relationships Matter Most (10:00) Friendship as a Daily Practice (12:31) Making New Friends as You Age (13:52) Social Media and Modern Loneliness (16:53) Why He Started Zen Practice (19:35) Nothing to Fix and Living Well (21:16) What Zen Meditation Really Is (23:11) Presence vs Dissociation (25:52) Why Happiness Is Not Constant (27:32) Attention as the Deepest Form of Love (30:21) Why Pain Always Passes (33:16) Robert Waldinger on Retirement (36:34) Learning to Trust Your Inner Signals Learn more about MEA at ⁠https://www.meawisdom.com/ #RobertWaldinger #HappinessResearch #GoodLife #Longevity #HealthyAging #Zen #Meditation #RelationshipsMatter #EmotionalWellbeing #Mindfulness #MentalHealth #HarvardStudy #PersonalGrowth #AgingWell #HumanConnection

    43 min

  5. 27 May

    How to Turn Anxiety Into Wisdom, Clarity, and Resilience

    Anxiety, burnout, and emotional overwhelm make a lot more sense once people understand what’s actually driving them. In this episode, Chip Conley, founder of MEA, former Airbnb executive, and bestselling author of Emotional Equations, talks with Derek Gehl about the hidden patterns behind anxiety, fear, purpose, and emotional resilience. Chip shares powerful insights on: Why anxiety comes from uncertainty and powerlessnessThe difference between fear and anxietyHow painful experiences become future wisdomWhy emotions begin in the bodyThe difference between purpose and emotional escape Chip also introduces his practical Anxiety Balance Sheet exercise, a simple tool designed to help people separate what they can control from what they can’t during stressful seasons of life. 📘 Want to dive deeper into Chip’s emotional frameworks and equations? Check out Emotional Equations here: https://www.chipconley.com/books/emotional-equations/ Timestamps: (00:00) Chip’s Emotional Equations book (02:30) Why emotions confuse so many people (4:06) Despair equals suffering minus meaning (06:10) Leading a company through crisis (08:57) What Bhutan taught Chip about happiness (11:03) The difference between fear and anxiety (14:27) How to regain control over anxiety (16:07) The anxiety balance sheet exercise (18:33) Wisdom as the square root of experience (20:28) Workaholism vs Calling Learn more about MEA at ⁠https://www.meawisdom.com/ #EmotionalEquations #Anxiety #FearVsAnxiety #EmotionalWisdom #EmotionalResilience #MentalHealth #Psychology #SelfAwareness #PersonalGrowth #StressManagement #MeaningAndPurpose #EmotionalIntelligence #ChipConley #MidlifeChrysalis #BurnoutRecovery

    23 min

  6. 25 May

    Why Deep Listening is the Key to Transformation | Gail Larsen

    The parts of ourselves we silence are often the very things that make us come alive. In this heartfelt episode of Midlife Chrysalis, I sit down with Gail Larsen, transformational speaking teacher, author, and longtime MEA faculty member, for a soulful conversation about authenticity, creativity, aging, and finding your voice. From growing up in a restrictive religious environment to helping thousands of people discover their “original medicine,” Gail shares the wisdom she’s gathered through decades of transformation and deep listening. Together, we explore: Why emotional connection matters more than polished performanceHow transformational listening helps us reconnect with ourselvesWhy our unique gifts are meant to be sharedHow entering the unknown keeps us fully aliveWhy transformation comes not from strategy, but from mystery This is one of those conversations that gently stays with you long after it ends. Timestamps: (02:22) Why Her 80s Feel Like the Best Years (04:18) Escaping a Restrictive Religious Life (07:19) Motherhood, Divorce, and Unexpected Paths (8:20) Madame Ovary and Finding Humor in Menopause (11:43) Her First Speech to 4,000 Women (13:34) Comfort Zone vs Home Zone Speaking (17:43) The Heart of Transformational Speaking (18:37) Discovering Your Original Medicine (20:13) What Makes a Speech Truly Transformative (22:43) Getting Out of the Jet Lag of Your Life (25:00) Why People Lose Themselves in Midlife (27:21) The Origins of Transformational Listening (32:15) Feeling Creatively Dried Up After COVID (34:26) Creativity, Soul, and Transformation (35:18) Menopause, Reinvention, and Santa Fe (40:54) Growing Older vs Growing Whole (43:27) Gail’s Biggest Life Lessons (45:11) Chip Conley on Cancer, Loss, and Wisdom Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeChrysalis #GailLarsen #TransformationalListening #Authenticity #PersonalGrowth #SelfDiscovery #TransformationalSpeaking #FindYourVoice #EmotionalHealing #MidlifeTransformation #Creativity #Purpose #DeepListening #SpiritualGrowth #AgingWisely

    49 min

  7. 22 May

    Why Success Alone Will Never Fulfill You | Brad Stulberg

    You hit your biggest goals… and still feel empty? In this episode, performance expert and bestselling author Brad Stulberg breaks down why success alone doesn’t fulfill us and what actually does. Drawing from his own experience with burnout, mental health struggles, and years of research, Brad shares a powerful new way to think about excellence, purpose, and what it really means to live well. Here are a few key takeaways: Success won’t save you: Chasing outcomes often leaves you feeling just as empty.Excellence is a practice: It’s about who you become, not what you achieve.Consistency beats intensity: Real mastery is built over years, not quick wins.Joy isn’t optional: It’s what makes the journey sustainable.You don’t have to grow from every struggle: Sometimes, surviving is enough If you’ve ever felt stuck, burned out, or wondering “Is this it?”, this conversation will change how you see success and your path forward. 👉 Watch now and rethink what truly matters. Timestamps: (03:01) What True Excellence Means (04:30) Early Influence and Life Direction (06:25) Mental Health Crisis & Turning Point (12:44) What “Gumption” Actually Means (14:26) Flow State Is Overrated (18:41) Why Joy Beats Discipline (25:14) Why Success Feels Empty (28:45) Enjoying the Process (31:20) Why Midlife Feels Hard (33:12) Finding Purpose Again (36:28) Self-Optimization Culture (41:17) Don’t Be One-Dimensional (44:37) Build a Bigger Life (46:20) Wisdom Bumper Sticker Learn more about MEA at ⁠https://www.meawisdom.com/ #excellence #meaningfullife #arrivalfallacy #selfimprovement #personaldevelopment #consistency #joyintheprocess #mastery #purpose #successmindset #mentalhealth #burnoutrecovery #growthmindset #habits #lifelessons

    52 min

  8. 20 May

    Why So Many Successful People Struggle With Retirement

    Why So Many Successful People Struggle With Retirement What Comes After Ambition but Before Retirement? The Hidden Midlife Crisis Between Success and Retirement  What happens when you stop chasing success… but you’re not ready to retire?  In this episode of Midlife Chrysalis, Chip Conley and Derek Gehl explore a stage of life many people experience but rarely talk about: feeling caught between ambition and retirement. Chip shares personal stories about aging parents, purpose, and how his own view of success changed over time. He explains why midlife can become less about proving yourself and more about giving back, mentoring others, and finding deeper meaning.  In this episode: • Why traditional success can start feeling empty • The difference between ambition and purpose • Why retirement doesn’t work for everyone • How to discover what really matters in the next chapter of life • A simple question that can help you find your calling If you’re rethinking what success, purpose, and aging really mean, this episode is for you. Watch now.  Timestamps: 00:00 Welcome to Wisdom Wednesday 01:14 The Hard Truth About Aging Parents 03:23 The New Life Stage Nobody Talks About 04:01 What Is Post Ambition Pre Retirement? 05:35 Stop Chasing Youth Start Growing Useful 08:17 How Airbnb Changed Chip’s Purpose 10:12 When Success Stops Being About You 12:05 Why Legacy Matters More Than Achievement 15:20 You Don’t Need a Huge Mission 16:00 The Grandmother Bench That Changed Lives 18:12 The Real Meaning of Your Gifts 19:18 Passion Always Requires Sacrifice 22:24 Why Retirement Often Feels Empty 23:30 How to Find Your Calling in Midlife  Learn more about MEA at ⁠https://www.meawisdom.com/  #MidlifeChrysalis #ChipConley #PostAmbitionPreRetirement #PAPR #ModernElder #MidlifePurpose #LifeAfterSuccess #RetirementTransition #PurposeAfter50 #AgingParents #MeaningInMidlife #SecondHalfOfLife #PersonalGrowth #WisdomWednesday #FindingYourCalling

    22 min
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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
    117
  • Rating
    Explicit
  • Copyright
    © Chip Conley
  • Show Website
    The Midlife Chrysalis

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