Education

The Midlife Chrysalis

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.

Latest Episodes:

When Success Isn't Enough: Finding Purpose in Midlife Jun 17, 2026

Show notes

Many successful people reach midlife with a surprising question: What's next?

In this episode of Wisdom Wednesday, Chip Conley shares what he's learning from leading the Purpose Fellowship, a year-long program helping people redefine purpose beyond career, achievement, and old identities.

Chip explores why so many high achievers struggle to find meaning after success, how hidden patterns influence our choices, and why purpose is often much broader than we realize.

In this conversation, you'll learn:

Why purpose is not just one thing for your entire life
How career identity can keep people stuck
The role of the "shadow" in shaping behavior and decisions
Why the shift from ego to soul becomes important in midlife
Four practical ways to reconnect with meaning and fulfillment

If you're navigating a life transition, questioning your direction, or looking for a deeper sense of purpose, this episode offers valuable insights and practical wisdom.

Listen now and start exploring what your next chapter could look like.

Timestamps:00:00 Introduction – The Midlife Chrysalis & Purpose

00:30 Welcome with Chip Conley and Derek Gehl

01:04 Chip's health update and prostate cancer treatment

02:05 MEA Homecoming, Richard Rohr workshop, and finding purpose

03:39 Why purpose matters and common misconceptions

05:17 Big P vs. Small P Purpose

06:46 The origin of the Purpose Fellowship

08:22 Why successful people struggle to find what's next

09:49 Building a Portfolio of Purpose

10:26 The Power 24 Assessment Tool

11:46 The lawyer who became a pastry chef

13:06 Who joins the Purpose Fellowship?

14:52 Common purpose challenges in midlife

15:46 Why achievers struggle to let go of success metrics

16:01 The “Stylus” metaphor and finding new music in life

17:02 Self-reflection, identity, and the Hero’s Journey

18:06 Understanding your shadow self

19:00 The danger of jumping onto a new treadmill

20:30 Letting go of old identities

22:41 The most overlooked area: Spiritual development

23:35 Moving from ego to soul in midlife

24:01 Four pathways to discovering purpose

25:00 Chip's current purpose experiments and passions

25:34 Family, fatherhood, and what matters most

26:07 Chip's new Substack and Wisdom Well26:33 Final thoughts and outro

Learn more about MEA at ⁠https://www.meawisdom.com/

#MidlifeChrysalis #MidlifePurpose #FindYourPurpose #MidlifeTransition #PersonalGrowth #LifeAfterSuccess #MeaningfulLife #PurposeDrivenLife #SecondHalfOfLife #MidlifeTransformation #SelfDiscovery #LifePurpose #PersonalDevelopment #ChipConley #MidlifeJourney

What Comes After You've Achieved Everything? | Bill George Jun 15, 2026

Show notes

He had the career, the success, and the recognition. So why was he miserable?

In this episode, Chip Conley sits down with leadership expert, bestselling author, and former Medtronic CEO Bill George to explore why success without purpose can leave even the most accomplished people feeling unfulfilled.

Drawing from personal loss, career setbacks, and decades of leadership experience, Bill shares the lessons that helped him discover his True North and build a life centered on meaning rather than achievement.

You'll learn:

Why success alone will never be enough
How adversity reveals who you really are
What it means to find your True North
Why authentic leadership starts with self-awareness
How to stay purposeful and engaged at every stage of life

Whether you're navigating midlife, rethinking your career, or searching for deeper meaning, this conversation offers timeless wisdom for living and leading with purpose.

Listen now and discover what happens when success gives way to meaning.

Timestamps:

(00:00) Intro

(00:38) Bill George’s Leadership Journey

(07:09) Loss, Grief, and Life Lessons

(10:24) The Honeywell Wake Up Call

(13:08) Discovering Purpose at Medtronic

(14:49) What Authentic Leadership Really Means

(18:28) How Crucible Moments Shape Leaders

(22:22) External Validation vs Inner Purpose

(25:03) Finding Your True North

(28:32) Exercises for Self Discovery

(30:54) Why Business Education Must Change

(35:42) Retirement and Staying Purposeful

(40:13) A Lifetime of Growth and Curiosity

(42:24) Midlife as a Time to Reflect

(43:38) Helping Others Reach Their Potential

(44:26) Three Lessons from Bill George

Learn more about MEA at ⁠https://www.meawisdom.com/

#MidlifeChrysalis #PurposeDrivenLife #TrueNorth #AuthenticLeadership #LeadershipDevelopment #PersonalGrowth #MidlifeTransformation #FindingPurpose #LifeLessons #LeadershipLessons #SelfAwareness #CareerGrowth #MeaningfulLife #ModernElder #BillGeorge

Stop Beating Yourself Up and Listen to This | Kristin Neff Jun 12, 2026

Show notes

Most of us are far kinder to other people than we are to ourselves and according to leading self-compassion researcher Kristin Neff, that may be one of the biggest reasons we struggle with stress, burnout, anxiety, and self-doubt.

In this episode, Kristin shares how discovering self-compassion through Buddhism and mindfulness changed her life during a difficult period of divorce, uncertainty, and intense self-criticism. She explains why self-compassion is not weakness or self-indulgence, but a proven tool for resilience, growth, motivation, and emotional wellbeing.

Chip and Kristin explore:

Why humans are naturally self-critical
The hidden cost of tying self-worth to achievement
How self-compassion improves performance and reduces anxiety
Why midlife often forces us to rethink success and identity
The difference between tender and fierce self-compassion

This episode is full of practical wisdom, emotional insight, and powerful reminders about what it truly means to care for yourself.

Watch now and learn why being kind to yourself can change the way you live, grow, and heal.

Timestamps:

(04:03) Divorce, Stress, and Self-Criticism

(05:28) Learning Mindfulness with Thich Nhat Hanh

(07:34) Why Most People Struggle with Self-Compassion

(10:06) The Power of Asking What Do I Need

(11:51) Why Women Often Ignore Their Own Needs

(13:13) Does Self-Compassion Reduce Motivation

(16:14) Stress, Performance, and Fierce Self-Compassion

(19:08) Growth Mindset and Self-Compassion

(22:08) Self-Compassion During Midlife

(24:15) Authenticity and Aging

(25:15) Letting Go of Old Success Scripts

(26:05) Hope, Optimism, and Emotional Resilience

(28:57) Can You Have Too Much Self-Compassion

(31:06) The Three Elements of Self-Compassion

(36:22) Self-Talk and Aging

(38:22) Aging, Appearance, and Self-Worth

(41:10) Spirituality and Compassionate Presence

(42:43) Wisdom, Kindness, and Life Lessons

(44:49) Final Thoughts on Being Kind to Yourself

Learn more about MEA at ⁠https://www.meawisdom.com/

#SelfCompassion #KristinNeff #Mindfulness #MidlifeGrowth #EmotionalResilience #MentalHealth #PersonalGrowth #SelfWorth #InnerCritic #MindsetShift #Authenticity #StressManagement #HealingJourney #MidlifeChrysalis #EmotionalWellbeing

Why Time Speeds Up as You Get Older (And How to Slow It Down) Jun 10, 2026

Show notes

Why does time seem to move faster every year?

One moment you're raising young children. The next, they're leaving home. So where does the time go?

In this Wisdom Wednesday, Chip Conley and Derek Gehl explore one of life's biggest mysteries: why time feels faster as we age and what we can do about it.

You'll discover:

Why being a beginner makes life feel longer
How flow states help us become fully present
The surprising link between mortality and happiness
Why purpose, mindset, and relationships matter more than any biohack
The powerful midlife mantra that can help you stop putting life off

Chip also shares a moving reflection on cancer, aging, and what he calls "holy urgency", a perspective that can change how you live today.

🎧 Watch now and learn how to create not just a longer life, but a fuller one.

Timestamps:

(00:00) One Year of Midlife Chrysalis

(01:24) Why Time Feels Faster as We Age

(03:40) What Happens in the Flow States

(04:31) Focusing on the Present

(07:11) Memento Mori and Carpe Diem

(09:06) Learning New Skills Later in Life

(10:13) How Children Experience Life

(11:05) The Importance of Flow and Presence

(12:40) Chip’s Upcoming Sabbatical

(15:00) Burning Man and the Principle of Immediacy

(16:46) Cancer and the Holy Urgency

(22:56) The Benefits of Mindset, Community, and Purpose

(24:11) How Mindset Shapes Health and Aging

(26:02) Designing Longevity Beyond Biohacking

Learn more about MEA at ⁠https://www.meawisdom.com/

#MidlifeChrysalis #ChipConley #WisdomWednesday #TimeFlies #MidlifeWisdom #MementoMori #FlowState #PurposeDrivenLife #PresentMoment #AgingWell #LongevityMindset #LifePurpose #PersonalGrowth #MeaningfulLife #MidlifeTransformation

What Research Reveals About America’s Midlife Crisis | Frank Infurna Jun 08, 2026

Show notes

Why do so many people feel overwhelmed, lonely, and unhappy in midlife?

Conley sits down with leading midlife researcher Frank Infurna to explore why so many middle-aged adults are struggling with stress, mental health challenges, and declining well-being, especially in the United States.

Drawing from years of research on aging and happiness, Frank explains why Americans report higher levels of loneliness and depression in midlife, why happiness often increases after 50, and how relationships, family, and purpose become more meaningful as we age.

They also discuss:

Why midlife is deeply misunderstood
The importance of community and social connection
How to approach your next decade with more intention
Why aging can improve emotional resilience and wisdom

This episode is insightful, hopeful, and filled with practical wisdom for anyone navigating change, rethinking their future, or entering a new phase of life.

Watch now and discover why the second half of life may hold more possibility than you think.

Timestamps:

(02:58) Why Frank Started Studying Midlife

(05:32) The Hidden Stressors of Midlife

(07:36) Why Americans Struggle More in Midlife

(10:06) How Other Countries Support Midlife Better

(12:09) Practical Advice for Surviving Midlife Stress

(14:52) Do Better Social Policies Improve Happiness?

(16:27) The Real Midlife Crisis Explained

(17:45) Why Midlife Is So Misunderstood

(22:50) Is the U-Curve of Happiness Real?

(25:18) Midlife as a Time of Reinvention

(28:17) What Should My Next 10 Years Look Like

(30:09) The Rise of Midlife Wisdom Schools

(32:40) Questions to Ask Yourself After 50

(34:56) What Gets Better with Age

(38:02) Wisdom Bumper Sticker

Learn more about MEA at ⁠https://www.meawisdom.com/

#Midlife #MidlifeCrisis #MidlifeWisdom #HealthyAging #Loneliness #MentalHealth #LifeAfter50 #MidlifeTransition #EmotionalWellbeing #PurposeInLife #AgingWell #FamilySupport #PersonalGrowth #Psychology #MiddleAge

The Truth About Becoming Miserably Successful | Debjani Biswas Jun 05, 2026

Show notes

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 inside
How fear and perfectionism quietly shape our lives
The surprising freedom that can come from a midlife crisis
The leadership qualities that matter most today
The 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

The Millennial Midlife Crisis Won't Look Like You Think Jun 03, 2026

Show notes

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 crisis
How the U-curve of happiness is changing for younger generations
Why millennials are shifting from freedom-seeking to stability-seeking
How longer lifespans are reshaping the concept of midlife
Why 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

The Decade Game That Can Transform Your Future | Carolyn Buck Luce Jun 01, 2026

Show notes

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 realize
What happens when you stop compartmentalizing your life
Why many women feel more confident and free in midlife
How imagining your future self changes your decisions today
The 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

What 88 Years of Research Revealed About Happiness | Robert Waldinger May 29, 2026

Show notes

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 money
The hidden loneliness behind social media and “curated lives”
What Zen practice teaches about anxiety, suffering, and being fully present
Why nobody is happy all the time and why that’s normal
How 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

How to Turn Anxiety Into Wisdom, Clarity, and Resilience May 27, 2026

Show notes

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 powerlessness
The difference between fear and anxiety
How painful experiences become future wisdom
Why emotions begin in the body
The 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

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