The Midlife Chrysalis

You can spend years chasing happiness and miss the life happening right in front of you.

In this episode of The Midlife Chrysalis, Chip Conley joins mindfulness teachers Mark Coleman and Lori Schwanbeck to explore how to feel more present, connected, and fully alive in midlife.

Together, they explore:

• How changing what you pay attention to can change your experience of life
• Why nature makes mindfulness easier and teaches us to let go
• How gratitude helps you appreciate your life, even when things are hard
• Why midlife’s losses and transitions can open the door to new possibilities
• How to quiet your inner critic and recognize your own worth

Watch the full episode for simple ways to step out of your head, reconnect with the world around you, and find more joy in the life you have.

Timestamps:

(06:27) Meet Mark and Lori

(07:23) Lori’s Path to Mindfulness

(10:34) From Punk Rock to Meditation

(13:03) Finding Peace in the Present

(15:42) How to Reframe Your Thoughts

(17:40) Mindfulness in a Distracted World

(19:53) Why Nature Helps Us Slow Down

(23:36) Making Meditation Easier Outdoors

(26:10) Why Midlife Sparks Inner Change

(29:53) Facing Mortality and Loss

(33:51) Psychedelics and New Possibilities

(37:13) Gratitude and Nature in Baja

(39:43) Making Gratitude a Daily Practice

(41:34) Gratitude Versus Gratification

(43:06) Remembering to Fully Live

(45:27) Making Peace with Your Inner Critic

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

#MidlifeChrysalis #ChipConley #MarkColeman #LoriSchwanbeck #Mindfulness #Midlife #MidlifeTransition #NatureMeditation #Gratitude #MindfulLiving #LettingGo #SelfCompassion #InnerCritic #PersonalGrowth #FindingJoy

The kids have moved out. Family gatherings feel complicated. Suddenly, the holidays you used to love leave you wondering where you belong.

In this Wisdom Wednesday episode, MEA founder Chip Conley joins host Derek Gehl to explore why holidays change in midlife and how new traditions can bring back a sense of connection.

Discover how to:

• Build celebrations around people you genuinely want to spend time with.
• Embrace Friendsgiving without the guilt of breaking with tradition.
• Find friendship and a fresh start through a holiday retreat.
• Plan a meaningful gathering without taking on all the work.

Watch now for inspiration to make this holiday season feel more connected, more joyful, and more your own.

Timestamps:

(00:00) Introduction

(01:44) How Holidays Change in Midlife

(02:14) Loneliness and Chosen Family

(06:14) Choosing Friendsgiving Over Family Drama

(07:20) Creating a New Year’s Tradition

(08:46) Holiday Retreats in Santa Fe and Baja

(11:05) Finding Connection During the Holidays

(12:03) Choosing Your Friendsgiving Guests

(12:41) Planning Ahead for the Holidays

(14:25) Making Holiday Gatherings Easier

(15:30) Upcoming Thanksgiving Workshops

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

#Midlife #Holidays #Friendsgiving #ChosenFamily #HolidayLoneliness #NewTraditions #ChipConley #MidlifeChrysalis #HolidayStress #Connection #Thanksgiving #FamilyDynamics #HolidayRetreats #MeaningfulHolidays #MEA

The hardest conversations are often the ones that help us grow.

John Baird has spent 30 years coaching leaders at Apple. At 82, he’s still coaching, trying new things, and making time for what matters most.

In this episode of The Midlife Chrysalis, John joins Chip Conley for a warm, candid conversation about leading with heart, making tough decisions, and building a meaningful life. He shares:

• How to hold people accountable while treating them with care.
• Why strong teams say the things everyone is thinking.
• How to turn your experience into a coaching career in midlife.
• Why revisiting your priorities matters in both work and marriage.
• How curiosity and gratitude keep life rich at any age.

Watch for practical wisdom on becoming a better leader and making more room for the people who matter to you.

Timestamps:

(02:31) Meet John Baird

(03:25) Rethinking Work, Marriage, and Family

(05:53) Coaching Leaders at Apple

(09:50) Steve Jobs’ Leadership After His Return

(11:26) Honest Feedback and Stronger Teams

(13:11) Leading with Heart and Toughness

(14:10) Seven Habits of Tough Leadership

(19:09) Helping Intel Navigate Change

(20:38) Finding Purpose at 82

(23:36) Becoming a Coach in Midlife

(27:55) Measuring Coaching Results

(29:59) Do You Need Coaching Credentials?

(31:36) Questions That Turn Insight into Action

(34:22) Curiosity, Gratitude, and Difficult Conversations

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

#JohnBaird #ChipConley #MidlifeChrysalis #Leadership #ExecutiveCoaching #LeadingWithHeart #ToughEnough #DifficultConversations #EmpatheticLeadership #SteveJobs #AppleLeadership #MidlifeReinvention #PurposefulLiving #PersonalGrowth #LifelongLearning

After everything you’ve been through, keeping your heart open can feel like a lot to ask. But there’s still room for connection, beauty, and a life that feels more like you.

Author and Omega Institute cofounder Elizabeth Lesser joins Chip Conley to explore how divorce, loss, and aging can deepen our lives without hardening our hearts. Drawing on her books Broken Open and the forthcoming Stay Open, she shares insights on how to:

• Find new possibilities when your old life falls apart.
• Question the stories that keep you apart from people you love.
• Make room for joy and grief at the same time.
• Meet your aging body with kindness and care.
• Stay open while holding healthy boundaries.

Join Chip and Elizabeth for a heartfelt conversation about what it takes to stay soft, stay curious, and keep growing through life’s changes.

Timestamps:

(02:37) What Is the Soul?

(05:47) Let Your Soul Lead in Midlife

(08:45) When Life Breaks You Open

(11:54) The Stories That Keep Us Apart

(13:40) How to Have Difficult Conversations

(18:00) How to Stay Open When Life Is Hard

(24:03) Finding Beauty Alongside the Pain

(26:20) Growing Older, Becoming More Whole

(28:47) What Gets Better With Age

(32:59) How Omega Institute Began

(38:13) Behind the Scenes of a Retreat Center

(42:30) Do No Harm, but Take No Shit

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

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

#ElizabethLesser #ChipConley #MidlifeChrysalis #BrokenOpen #StayOpen #OmegaInstitute #MidlifeTransformation #HealthyAging #PersonalGrowth #EmotionalHealing #SpiritualGrowth #Relationships #GriefAndLoss #SelfCompassion #Boundaries

“Stay positive” can feel hollow when cancer returns, someone you love dies, and your marriage is ending.

In this Wisdom Wednesday episode, MEA founder and author Chip Conley joins Derek Gehl for a deeply personal conversation about facing all three. Drawing on his upcoming book, The Art of the Reframe, Chip shares how he’s finding a way forward without pretending the pain isn’t real.

You’ll discover how to:

• Feel the grief before trying to find the silver lining.
• Separate what happened from the story you tell yourself about it.
• Rethink the belief that a marriage ending means it failed.
• Find new possibilities through a simple reframing practice.
• Build deeper friendships by opening up about what’s really going on.

Watch for an honest conversation about loss, love, and changing your perspective when you can’t change your circumstances.

Timestamps:

(00:00) The Art of the Reframe

(01:20) When Life Changes All at Once

(04:33) Reframing Without Ignoring Grief

(06:02) Letting Yourself Feel

(07:24) Understanding Your Frame

(10:44) Rethinking Love and Connection

(15:21) Breaking Free from Feeling Stuck

(16:14) Routines, Rituals and New Perspectives

(17:58) Deeper Friendships and Honest Conversations

(19:04) Men, Vulnerability and Emotional Support

(22:54) A Simple Reframing Practice

(26:02) Psychedelics and Changing Perspective

(27:20) Learning to Let Go

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

The Art of the Reframe PRE-SALE: http://meawisdom.com/reframebook

#ChipConley #DerekGehl #WisdomWednesday #MidlifeChrysalis #TheArtOfTheReframe #ModernElderAcademy #Reframing #MidlifeTransitions #LifeTransitions #NavigatingGrief #MarriageEnding #EmotionalResilience #FeelingStuck #ToxicPositivity #MaleVulnerability

You can build a successful life and still reach a point where you need to rebuild yourself.

In this episode, Chip Conley sits down with David Gottfried, co-founder of the U.S. Green Building Council and pioneer of the green building movement, for a candid conversation about success, loss, and reinvention.

David shares how transforming an industry was followed by a deeply personal transformation when his 20-year marriage ended and forced him to rethink who he was.

They explore:

• How green building went from a fringe idea to a global movement

• Why hiding parts of ourselves can come at a profound cost
• What divorce taught David about vulnerability and letting others in
• Why letting go of old identities can open the door to a new life
• Why regeneration must go beyond our planet to include ourselves

David’s lesson from it all is simple: “Truth is oxygen.”

Watch the full episode for an honest conversation about success, identity, and finding the courage to become

Timestamps:

(06:13) From Stanford to Real Estate

(10:06) Bringing Solar Into Development

(12:00) Founding the U.S. Green Building Council

(17:12) Making Green Building Mainstream

(20:17) How LEED Took Off

(22:05) A Midlife Transformation

(26:25) Divorce and a Personal Chrysalis

(31:05) What Pain Taught Him

(33:45) No More Hiding

(35:04) The Dark Night of the Ego

(37:05) From Sustainability to Regeneration

(43:14) What Gives Him Hope

(45:08) Truth Is Oxygen

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

#DavidGottfried #ChipConley #MidlifeChrysalis #GreenBuilding #USGBC #LEED #RegenerativeLiving #MidlifeReinvention #PersonalTransformation #LifeAfterDivorce #FindingYourself #Vulnerability #Sustainability #Regeneration #SecondHalfOfLife

Your first love can stay with you for decades. So can the story you keep telling yourself about it.

Actor and filmmaker Juan Pablo Di Pace joins Chip Conley for a personal conversation about love, memory, and the past’s hold on our present. Through his film Before We Forget, he revisits a formative teenage love and explores how a memory can be both something we treasure and a wound we carry.

He shares:

• Why romanticizing the past can keep us from moving forward.
• How old videotapes brought powerful teenage emotions back to life.
• What it feels like to watch actors recreate moments from your own life.
• How unexpected friendships can become a chosen family.
• Why trusting your passion matters more than other people’s opinions.

Watch for an intimate look at first love, creative courage, and the memories that follow us into midlife.

Timestamps:

(10:08) Meet Juan Pablo Di Pace

(10:47) A Life of Travel and Creativity

(12:04) From Actor to Filmmaker

(14:23) Admission and Finding Your People

(18:47) The Story Behind Before We Forget

(24:19) Memory and Romanticizing the Past

(27:38) Turning Personal Experience Into Film

(33:13) Bringing Before We Forget to Audiences

(35:31) Playing Jesus and Being Yourself

(40:48) Advice to His Younger Self

(42:28) Follow Your Passion and Study the Greats

(45:26) The MEA Film Fest and New Friendships

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

Before We Forget TRAILER: https://beforeweforgetmovie.com/

#JuanPabloDiPace #ChipConley #MidlifeChrysalis #BeforeWeForget #DuinoFilm #FirstLove #UnrequitedLove #LoveAndMemory #Midlife #PersonalStorytelling #AutobiographicalFilm #Filmmaking #ChosenFamily #AdmissionFilm #MEAFilmFest

Watch a great film, then share dinner with the person who made it. That’s the spirit of the MEA Film Fest, where stories on screen spark conversations and connections in real life.

In this Wisdom Wednesday episode, Chip Conley joins Derek Gehl to preview the festival and explore a question at its heart: how can movies help us see midlife, aging, and our own possibilities differently?

• Get a preview of the films, special guests, and festival experience.
• Discover stories of reinvention that go beyond the midlife crisis.
• Explore what your reactions to characters reveal about your hopes and fears.
• Bring those conversations home with a simple movie night exercise.

Tune in for films worth watching, people worth meeting

Timestamps:

(01:02) Chip’s Love of Film

(02:50) Inside the MEA Film Fest

(04:17) Midlife Crisis on Screen

(07:44) How Movies Shape Our View of Aging

(10:04) Starting a Film Club

(11:20) Films to Watch and Discuss

(14:51) What Movie Characters Reveal About You

(15:44) Finding Meaning in It’s a Wonderful Life

(17:06) Closing Thoughts

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

#ChipConley #MidlifeChrysalis #WisdomWednesday #MEA #MEAFilmFest #Midlife #MidlifeTransformation #Aging #Ageism #Movies #FilmClub #Reinvention #PersonalGrowth #MeaningfulConnections #SecondAct

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

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