The Midlife Chrysalis

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 WorkshopsLearn 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 ConversationsLearn 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 ShitLearn 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 GoLearn 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 movementWhy hiding parts of ourselves can come at a profound costWhat divorce taught David about vulnerability and letting others inWhy letting go of old identities can open the door to a new lifeWhy regeneration must go beyond our planet to include ourselvesDavid’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 becomeTimestamps:(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 OxygenLearn more about MEA at ⁠https://www.meawisdom.com/#DavidGottfried #ChipConley #MidlifeChrysalis #GreenBuilding #USGBC #LEED #RegenerativeLiving #MidlifeReinvention #PersonalTransformation #LifeAfterDivorce #FindingYourself #Vulnerability #Sustainability #Regeneration #SecondHalfOfLife