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:

From Nike CEO to Starting Over at 65: John Donahoe’s Reinvention Oct 12, 2026

Show notes

After decades at the top, John Donahoe found himself starting over at 65.

John has led eBay, ServiceNow, and Nike. But some of his most important lessons came from burnout, failure, and the difficult transitions between success and what comes next.

In this deeply personal conversation, John shares:

Why stepping away at 55 changed the way he saw success and himself
What 50 wise elders taught him about vitality, purpose, and aging
How his painful departure from Nike challenged his identity at 65
Why adversity can become a source of meaning and growth
How an unexpected opportunity at Stanford became his next chapter

This is a powerful conversation about starting again, letting go of outcomes, and finding purpose beyond achievement.

Watch the full episode with John Donahoe.

Timestamps:

(03:16) Reinventing Life After 50

(05:07) Burnout and Taking a Year Off

(07:56) The Retreat That Changed Everything

(10:21) Leaving the Gladiator Ring

(13:59) The Search for Vitality

(16:12) Lessons From 50 Wise Elders

(20:15) Service, Purpose and Serendipity

(23:24) The Road to Nike

(28:04) Crisis and Failure at Nike

(33:15) Lessons From Failure

(37:26) A New Chapter at Stanford

(41:09) Finding Purpose Again

(44:15) The Gift of Adversity

(47:33) Turning Pain Into Wisdom

Check out Chip's Celebrating Life's Wisdom Oct 25-29 2026 workshop: https://www.meawisdom.com/celebrate

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

#JohnDonahoe #NikeCEO #LifeAfterNike #StartingOverAt65 #MidlifeReinvention #WisdomJourney #LeadershipLessons #CareerReinvention #SecondAct #FindingPurpose #Adversity #LifeTransitions #StanfordAthletics #PurposeAfterSuccess #MidlifeChrysalis

When the Life You Built Is No Longer Enough | Caroline Myss Oct 09, 2026

Show notes

Midlife can feel like the life you built suddenly stops fitting. Caroline Myss believes there’s a deeper reason: this is when the soul begins asking something different of you.

In this powerful conversation, bestselling author and spiritual teacher Caroline Myss joins Chip Conley to explore the deeper meaning of midlife, purpose, identity, and surrender.

Caroline shares:

Why a crisis of purpose may actually be a crisis of the soul
How we move from job to career to calling
Why we lose our appetite for the life we’ve built
How sacred contracts shape our relationships and challenges
Why surrender means releasing fear and control

Chip also opens up about his near-death experience and changing identity as Caroline challenges him to see his life through a different lens.

Watch the full conversation for a profound look at what happens when the life that once fit you is no longer enough.

Timestamps:

(3:36) Midlife and the Search for Wisdom

(9:15) The Rise of the Inner Self

(13:56) When a Crisis Is Spiritual

(14:40) What Is Wisdom?

(15:30) Sacred Contracts and the Power of Choice

(20:45) The People We’re Meant to Meet

(23:55) How to Recognize a Sacred Contract

(27:16) From Job to Career to Calling

(31:00) Why Midlife Changes Us

(36:25) Chip’s Near-Death Experience

(38:30) Wounds, Identity, and Illness

(44:24) Learning to Surrender

(47:12) Carolyn’s Hard-Won Wisdom

(48:02) God Is Law

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

#CarolineMyss #ChipConley #Midlife #MidlifeWisdom #MidlifeCrisis #SpiritualAwakening #SpiritualGrowth #SacredContracts #FindingPurpose #LifePurpose #PersonalTransformation #FindingYourCalling #SoulPurpose #Wisdom #Surrender

What If the Life You Built Isn’t the Life You Want? Oct 07, 2026

Show notes

You’ve built a life that looks successful. Yet the things you worked so hard for may no longer be what you want next.

In this Wisdom Wednesday episode, MEA founder Chip Conley joins Derek Gehl to explore finding purpose when familiar roles no longer feel fulfilling. From a corporate lawyer investing in her community to former business owners pursuing screenwriting, Chip shares how people are discovering possibilities they had quietly put aside.

You’ll hear:

How to recognize someone else’s success script and begin defining success for yourself.
Four pathways to purpose: what excites you, agitates you, makes you curious, or feels neglected.
Why smaller purposes matter, from learning guitar to making more time for your children.
A question to clarify your priorities: what will you regret not learning or doing 10 years from now?
A simple exercise to find direction through the moments when you feel useful and lose track of time.

Watch the full episode for a thoughtful look at what deserves your time now and what you’d love to make room for next.

Timestamps:

(00:00) Introduction

(00:37) The myth of one purpose

(01:41) Why purpose matters in midlife

(03:36) Passion, purpose and ikigai

(04:40) Four pathways to purpose

(05:39) The MEA Purpose Fellowship

(08:30) Creating a purpose portfolio

(09:40) Finding purpose beyond career success

(12:54) Why community helps you find purpose

(14:56) Purpose after retirement and an empty nest

(17:29) Rethinking relationships

(18:25) Chip’s personal purpose portfolio

(20:34) Making room for small purposes

(21:59) A simple exercise to discover your purpose

(23:06) Ways to explore purpose with MEA

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

#Midlife #Purpose #ChipConley #DerekGehl #WisdomWednesday #MidlifeChrysalis #FindingPurpose #LifePurpose #MidlifeTransition #PersonalGrowth #MeaningfulLife #RedefiningSuccess #LifeAfter50 #SelfDiscovery #MEA

He Died 11 Years Ago. Their Relationship Never Ended. | Lucy Kalanithi Oct 05, 2026

Show notes

Eleven years after losing her husband, the pain has changed. The love hasn’t.

Dr. Lucy Kalanithi, physician and widow of Paul Kalanithi, author of When Breath Becomes Air, joins Chip Conley for a deeply personal conversation about grief, caregiving, uncertainty, and building a meaningful life after profound loss.

Drawing on her experience as a wife, mother, caregiver, and doctor, Lucy shares what more than a decade of living with grief has taught her:

Why death doesn’t necessarily end our relationship with someone we love
How grief changes over time, even when the love remains
Why caregivers need permission to ask for help and protect themselves
How losing Paul changed the way she cares for patients and their families
How to live with uncertainty when there are no clear answers

Watch the full episode for a moving perspective on love, loss, and what it means to keep living when life changes forever.

Timestamps:

(04:14) Lucy Kalanithi’s Story

(05:20) When Breath Becomes Air

(06:40) Staying Connected After Loss

(13:20) How Grief Changes Over Time

(14:18) Advice for Living With Grief

(16:04) How Loss Changed Her as a Doctor

(18:44) The Reality of Caregiving

(21:06) What Caregivers Really Need

(23:45) Living With Uncertainty

(27:33) Finding Acceptance in the Unknown

(31:42) Serenity, Courage, and Wisdom

(35:05) Raising a Child After Loss

(38:13) Wisdom Bumper Sticker

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

Be part of the conversation at the End Well Conference in Los Angeles on November 12, where Lucy Kalanithi and Chip Conley will take the stage to explore how we can live, care, and face life’s biggest transitions with greater meaning.

Learn more and get tickets: https://endwellproject.org/end-well-2026/

#LucyKalanithi #PaulKalanithi #WhenBreathBecomesAir #Grief #LifeAfterLoss #LoveAfterLoss #Bereavement #Caregiving #LivingWithLoss #Mortality #Uncertainty #Acceptance #MidlifeWisdom #ChipConley #MidlifeChrysalis

Why Life Can Get Harder and Happier After 50 | Jonathan Rauch Oct 02, 2026

Show notes

Jonathan Rauch had reached the top of his career, yet each year he felt less satisfied. Then came the loss of his parents, his job, and a startup he had tried to build. To his surprise, his sense of contentment began to grow.

Rauch is a journalist and the author of The Happiness Curve, The Constitution of Knowledge, and Cross Purposes. He joins Chip Conley to explore what his personal experience and research reveal about getting older, and why the future looks more troubling for younger adults.

In this conversation:

Why achievement does not always bring the happiness we expect
Why life satisfaction often rises after 50, even through setbacks
Why young adults’ loss of hope concerns Rauch
Why free speech alone is not enough to establish what is true
How wisdom helps us navigate conflict, and why it can be taught

Watch for an honest, thought-provoking conversation about happiness, truth, and the value of staying curious throughout life.

Timestamps:

03:49 Seeing what others miss06:59 The midlife happiness curve10:31 Why life can get better after 5012:21 Why young adults are losing hope15:49 How society knows what is true20:57 Wisdom in an age of disinformation24:53 Advice for the next generation26:34 Staying curious as we age

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

#JonathanRauch #ChipConley #TheHappinessCurve #HappinessAfter50 #MidlifeHappiness #AgingWell #LifeSatisfaction #YoungAdultHappiness #Wisdom #Truth #Disinformation #ConstitutionOfKnowledge #ModernElder #MidlifeWisdom #Curiosity

The Hardest Leadership Lesson: Let Someone Else Be the Hero Sep 30, 2026

Show notes

Being the person who saves the day feels good. But letting someone else do it can make you a better leader.

MEA founder Chip Conley joins Derek Gehl to talk about one of the hardest changes in his career: moving from hero to coach. Chip shares how he is learning to step back, trust his team, and make room for others to lead.

Why having all the answers can hold your team back
How asking questions helps others grow into leaders
Why purpose matters as an organization gets bigger
How to build something that can thrive without you
What leadership can become in your next chapter

Watch the full episode to hear Chip’s candid take on letting go and leading with greater wisdom.

Timestamps:

(00:00) Intro

(02:30) From Hero to Coach

(04:39) Bill George and Purpose Driven Leadership

(07:40) Learning to Lead Together

(10:06) Servant Leadership

(11:20) Finding Meaning in Work

(12:31) Leadership as a Practice

(14:19) Building Culture Across an Organization

(16:09) Building an Organization That Thrives Without You

(18:25) Your Next Chapter of Leadership

(22:48) The Bill George Workshop

(25:17) A Leadership Experiment

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

Listen to the podcast episode with Bill George, CEO of Medtronic: https://youtu.be/M9PuSyubTB0

#ChipConley #Leadership #LeadershipDevelopment #WiseLeadership #MidlifeLeadership #ServantLeadership #FounderLeadership #LeadershipCoaching #Mentorship #PurposeDrivenLeadership #OrganizationalCulture #BillGeorge #ModernElder #WisdomWednesdays #TeamLeadership

What Changes When You Finally Let Go of Control? | Thomas DeLong Sep 28, 2026

Show notes

Success can look impressive on a résumé and still leave you wondering who you really are.

At 76, Harvard Business School professor and former Morgan Stanley executive Thomas DeLong is rethinking some of the biggest lessons he has learned about leadership, courage, relationships, and success.

In this conversation with Chip Conley, he reflects on:

Why letting go of control can deepen relationships
How to move from image management to essence
Why vulnerability is a powerful form of courage
How inherited success scripts can define the path we follow
Why later life is about investing wisdom, not just retiring

From family and leadership to identity and aging, DeLong shares the hard-earned lessons that have changed how he sees himself and the people around him.

Watch now for a deeply personal conversation about letting go, finding courage, and defining success on your own terms.

Timestamps:

(02:40) Letting Go of Control

(04:31) Building Closer Relationships

(07:20) Vulnerability With His Daughters

(09:35) Courage and Self-Doubt

(13:00) Courageous Life Decisions

(16:45) From Image to Essence

(20:44) Changing Leadership at Morgan Stanley

(23:38) The Parable of the Sadhu

(26:04) Measuring a Meaningful Life

(30:58) Investing Wisdom in the Next Decade

(34:00) Sing Loudly and in Harmony

(36:10) Breaking Free From the Success Script

(38:36) A New Definition of Success

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

Watch Chip’s Soul Biography, created by filmmaker Nic Askew: MEAWisdom.com/Soul

#ThomasDeLong #ChipConley #MidlifeChrysalis #HarvardBusinessSchool #Leadership #RedefiningSuccess #PersonalGrowth #SelfAcceptance #Vulnerability #Courage #LettingGo #MidlifeWisdom #AuthenticLeadership #LifeLessons #HealthyAging

Let Life Lead: A Different Way to Navigate Midlife | Nic Askew Sep 25, 2026

Show notes

Sometimes the most powerful way forward begins by doing less.

Filmmaker Nic Askew has spent more than two decades capturing what happens when people stop performing and simply allow themselves to be seen. Through his Soul Biographies, he has discovered a different way of approaching connection, identity, and life itself.

In this episode, Nic explores:

Why “starting with nothing” can reveal what effort cannot
How stillness creates space for the soul rather than the ego to lead
Why doing less can help us truly see and connect with others
How letting go of control can reveal what comes next in lifeIt’s a fascinating conversation about soul, human connection, and learning to let life lead.

Watch the full episode and discover the power of starting with nothing.

Timestamps:

(03:24) Discovering Filmmaking at Midlife

(04:18) Picking Up a Camera

(08:54) A Calling Out of Nowhere

(12:14) Starting With Nothing

(16:53) The Soul Biographies

(17:32) Speaking From Ego vs. Soul

(19:17) Letting Life Lead

(23:48) Stillness Before Action

(28:13) Truly Seeing Others

(31:07) Deepening Connection

(37:34) Filming the MEA Community

(42:13) Seeing Beyond the Persona

(46:51) Nic’s Life Wisdom

The Soul of MEA, the link is: MEAWisdom.com/Soul

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

#NicAskew⁠ ⁠#SoulBiographies⁠ ⁠#Midlife⁠ ⁠#MidlifeTransformation⁠ ⁠#PersonalGrowth⁠ ⁠#SelfDiscovery⁠ ⁠#AuthenticLiving⁠ ⁠#LifePurpose⁠ ⁠#HumanConnection⁠ ⁠#Stillness⁠ ⁠#SoulWork⁠ ⁠#MidlifeWisdom⁠ ⁠#LetLifeLead⁠ ⁠#Presence⁠ ⁠#MEA

Be Useful, Not Youthful: The Secret to Aging Well Sep 23, 2026

Show notes

At some point in midlife, achievement stops being enough. The titles matter less, the phone may stop ringing, and the question becomes: where does your value come from now?

In this episode of Wisdom Wednesday, MEA founder Chip Conley joins Derek Gehl to explore the shift from achievement and admiration toward generativity, usefulness, and helping others grow.

Key insights include:

Why feeling invisible doesn’t mean becoming irrelevant
How to move from “sage on the stage” to “guide on the side”

Why being useful matters more than staying youthful

How becoming “good soil” helps other people and future generations flourish
Why doing good without getting credit can be one of the most meaningful forms of contribution

Watch the full episode to discover a different way to think about purpose, relevance, and growing older.

Timestamps:

(00:00) Welcome to Wisdom Wednesday

(00:41) The Sacred Pause

(03:48) Becoming Good Soil

(05:43) Regenerating Soil and Soul

(07:55) Shifting Roles in Midlife

(08:30) From Sage to Guide

(10:21) Generativity vs. Stagnation

(13:47) Staying Generative After Retirement

(15:20) Feeling Invisible in Midlife

(15:59) What You Have to Offer

(18:55) Be Useful, Not Youthful

(19:15) Finding a New Role

(21:19) Crystallized Intelligence

(22:26) Give Without Getting Credit

(23:55) Letting Others Grow

(25:12) Quiet Generosity

Check out Chip's Celebrating Life's Wisdom Oct 25-29 2026 workshop: https://www.meawisdom.com/celebrate

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

#ChipConley #MidlifeChrysalis #ModernElderAcademy #WisdomWednesday #Generativity #MidlifePurpose #LifeAfter50 #AgingWell #MidlifeWisdom #CrystallizedIntelligence #PurposeAfter50 #Mentorship #MidlifeTransition #SacredPause #GoodSoil

Can Your Beliefs Actually Change How You Age? | Shawn Achor Sep 21, 2026

Show notes

We’re taught to expect decline as we get older. But the science tells a far more hopeful story.

In this episode, bestselling author and positive psychology expert Shawn Achor joins us to explore how our beliefs can shape the way we age. Drawing from his new book, The Power of Beliefs, groundbreaking research, and his own midlife experience, Shawn reveals why getting older can bring new opportunities for growth, meaning, happiness, and wisdom.

You’ll discover:

How beliefs about aging can influence our physical and cognitive outcomes

Why midlife doesn’t have to mark the beginning of decline
How negative expectations can become powerful nocebo effects
Why life can become more meaningful even as our priorities change
How “neuroscaping” can reshape the stories we tell about our lives

From stepping away from career success to rediscovering what truly matters, Shawn offers a compelling new perspective on aging and the potential that remains ahead.

Watch now to discover why your beliefs about getting older may matter more than you think.

Timestamps:

(03:04) Finding Joy and Wonder in Family Life

(04:54) Rethinking Potential in Midlife

(09:07) How Fatherhood Changed His Priorities

(12:47) Feeling Replaced and Rediscovering Meaning

(15:20) How Divinity School Reshaped His Faith

(20:16) The Power of Beliefs

(24:18) The Nocebo Effect

(25:38) How Beliefs About Aging Shape Outcomes

(29:09) Optimism and the U-Curve of Happiness

(34:11) Why Meaning Can Grow With Age

(38:51) Neuroscaping Your Memories

(45:59) Turning Possibility Into Reality

(47:21) Why Happiness Leads to Success

(50:58) Growing Wiser With Age

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

#ShawnAchor #PositivePsychology #PowerOfBeliefs #Midlife #HealthyAging #PsychologyOfAging #Happiness #Mindset #AgingWell #PersonalGrowth #MeaningAndPurpose #Optimism #Neuroscaping #MidlifeGrowth #SuccessfulAging

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