The Midlife Chrysalis

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