The Midlife Chrysalis

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

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

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

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

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