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The Midlife Chrysalis

Chip Conley
The Midlife Chrysalis
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  • Why Krista Tippett Walked Away at the Peak of Her Career
    What happens when one of the most thoughtful voices in public life hits a wall?In this deeply personal conversation, Krista Tippett opens up about burnout, walking away from success, and rediscovering joy in midlife. From letting go of exhaustion to falling in love again, she shares the hard-won wisdom that’s reshaping how she lives, works, and loves. It’s a moving reminder that it’s never too late to begin again, so don’t miss this one.Subscribe for more powerful conversations that spark reflection, reinvention, and real change in midlife.Timestamps:00:00 Welcome and Setup00:46 Introducing Lee and the Unique Cast of Guests01:52 What Makes a Great Interviewer?06:12 Interviewing John O’Donohue09:57 Thresholds and Transitions12:58 Krista’s Childhood and Upbringing in Oklahoma17:40 The Bible as Her First Text of Imagination20:00 Interviewing Richard Rohr and Men’s Spiritual Lives23:36 Krista’s Midlife Reflections27:06 Midlife Chrysalis and Personal Transformation30:53 Building a Life Around Love and Friendship35:36 What She’d Regret Not Doing38:09 What Brings Joy Now42:03 Defining Wisdom and Growing Wiser46:26 Staying Grounded Through Rituals and Attention51:43 Rethinking Retirement54:29 The Aging Brain and Synthesizing Wisdom57:46 Wisdom Bumper StickerLearn more about MEA at ⁠https://www.meawisdom.com/#MidlifeWisdom #OnBeing #KristaTippett #MidlifeTransformation #SpiritualGrowth #LifeAfter40 #InnerLife #FindingPurpose #EmotionalResilience #WomenOver40 #BecomingWise #SoulfulLiving #PersonalGrowthJourney #AgingWithGrace #DeepConversations
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  • What Burning Man Teaches Us About Aging, Identity & Legacy | Marian Goodell
    What if your so-called “midlife crisis” was actually a doorway to reinvention? In this powerful conversation, Burning Man CEO Marian Goodell joins Chip Conley to explore how the radical spirit of Burning Man offers surprising lessons on aging, identity, leadership, and legacy. From embracing impermanence to finding purpose without a script, this episode is a deep dive into how midlife can be your most creative and meaningful chapter yet.Timestamps:00:00 Intro00:40 Chips Connection to Burning Man04:43 What Burning Man Really Is07:01 How Burning Man Became a Global Movement08:47 The Core Principles That Guide Everything11:13 Radical Self-Expression and Creating Without Expectation13:38 Why Burning Man Attracts People in Midlife Transition16:43 Loss, Legacy, and What We Leave Behind21:46 Lessons from Larry Harvey as a Modern Elder25:05 What She Learned as a Burning Man’s CEO33:00 What Is Fly Ranch and Why It Matters36:28 Fly Ranch Like Burning Man’s Feminine Side39:24 Three Tips for Burning Man First-Timers42:14 Burning the Man and Temple Rituals47:22 The Healing Power of Ritual50:08 Why MEA Resonates with Burners53:40 Wisdom Bumper StickerLearn more about MEA at ⁠https://www.meawisdom.com/#BurningMan #MidlifeCrisis #MidlifeTransformation #MarianGoodell #BurningMan2025 #PersonalGrowth #ReinventionAfter40 #MidlifeAwakening #LifeAfter50 #SpiritualJourney #BurningManExperience #RadicalSelfExpression #MidlifeChrysalis #ChipConley #PurposeInMidlife
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  • Psychedelics, Purpose & the Next Chapter of John Mackey’s Life
    What does it really take to start over at 69?In this inspiring episode, Whole Foods founder John Mackey shares how psychedelics, purpose, and love reshaped his path after selling to Amazon.From ego death to building Love Life wellness centers, he opens up about business regrets, spiritual breakthroughs, and midlife transformation. You'll learn how conscious capitalism evolves with age—and why love might be the ultimate business strategy.Subscribe for more honest conversations about midlife renewal, purpose-driven living, and personal reinvention.Timestamps:00:00 Intro00:27 Meet John Mackey01:27 Psychedelics, Ego Death, and Food as Purpose07:44 Love, Breakups, and Big Business Shifts08:37 Austin in the '70s and Building Whole Foods10:40 Advice to His Younger Self12:34 From Atheism to Spiritual Adventure14:36 What Is Conscious Capitalism?17:15 How Whole Foods Revolutionized Grocery Stores19:28 Learning to Communicate with Kindness21:46 Selling Whole Foods to Amazon28:17 Why He Finally Left Whole Foods29:25 Healing Journey Through Plant Medicine31:28 What Is Love Life?37:56 Psychodelics as Therapeutic Method40:21 Challenges and Financial Realities43:21 Longevity Myths and What Actually Works47:49 Redefining Retirement with Purpose49:54 What He’d Regret Not Doing52:09 Wisdom Bumper Sticker55:33 Final ReflectionsLearn more about MEA at ⁠https://www.meawisdom.com/#JohnMackey #WholeFoods #ConsciousCapitalism #MidlifeTransformation #LongevityTips #PlantMedicine #PsychedelicHealing #PurposeDrivenLife #HolisticHealth #LoveLifeWellness #SpiritualGrowth #EntrepreneurMindset #ChipConley #FoundersJourney #ReinventYourself
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  • Rich Roll on Reinventing Yourself After Rock Bottom
    What if hitting rock bottom was the best thing that ever happened to you?In this raw and inspiring conversation, Rich Roll, a former addict turned world-class endurance athlete, shares how he rebuilt his life from scratch, facing failure, financial ruin, and identity loss to find real purpose.With brutal honesty, he opens up about his addiction, fatherhood, marriage, legacy, and the heavy cost of chasing approval. If you're feeling stuck, burned out, or unsure what comes next, this conversation just might change how you see your own story.Timestamps:00:00 Introduction 01:13 Spine Surgery and Recovery03:02 Losing Identity and Facing Stillness05:47 Interviewing Master Interviewers07:17 Life Begins at 40 & Rejecting the Race11:06 How to Know You’re on the Right Track13:42 Performance vs. Presence15:25 Addiction, Achievement, and the Roots of Disconnection19:49 The Midlife Chrysalis at Age 3924:29 The Support of His Wife Julie26:04 Lessons from Rich’s Midlife Chrysalis32:14 From Blog to Writing a Book38:10 Launching the Podcast & Relocating to Hawaii42:27 Gaining Momentum43:50 Financial Struggles and Family Impact48:14 What Makes Rich Roll’s Podcast Different51:58 The Importance of Genuine Curiosity54:25 The Power of Vulnerability in Conversation56:31 Rethinking Success and Slowing Down01:01:46 Legacy, Family, and Showing UpLearn more about MEA at ⁠https://www.meawisdom.com/#MidlifeTransformation #RichRoll #SpineSurgeryRecovery #SobrietyJourney #PurposeInMidlife #EnduranceAthlete #AddictionRecovery #MidlifeReinvention #PersonalGrowth #PodcastLife #EmotionalResilience #LifeAfter40 #LegacyWork #AuthenticLiving #ModernElder
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  • Reinvention After 50 with Seth Godin: Make Life Your Best Work of Art
    What if midlife isn’t a crisis, but your most creative chapter yet?In this inspiring and deeply personal episode, bestselling author and entrepreneur Seth Godin shares how he’s reinvented his life through purpose-driven work, disciplined freedom, and the belief that life itself is a series of art projects.We explore why the “dip” is a crucial part of growth, how to walk away from success when it no longer serves you, and what it really means to build a legacy. Seth also opens up about aging, identity, and choosing meaning over momentum.It’s a conversation full of wisdom, honesty, and practical insight for anyone navigating change. Subscribe for more episodes that help you reimagine your next chapter!Timestamps:00:00 Intro01:16 How Seth and Chip first met at Stanford02:49 Writing their first book together03:53 Jay Conrad Levinson as a modern elder07:01 Writing over 150 books08:31 Understanding The Dip and its midlife parallels12:28 Seth’s two “Dip” examples14:13 Chip’s hotel dip and decision making17:27 Creativity, resilience, and entrepreneurship after 5019:36 Not being in high school anymore & insulating yourself22:49 Midlife crisis or chrysalis?27:25 Alt MBA, The Carbon Almanac, and collaborative creation32:03 Rebranding midlife and self-image as we age35:28 Things that got better with aging37:54 Seth’s perspective on retirement & legacy41:16 Seth’s next project42:42 The future of the U.S. and generational change46:28 A bumper sticker of wisdom48:14 The importance of the origin storyLearn more about MEA at https://www.meawisdom.com/#SethGodinInterview #MidlifeChrysalis #StanfordStories #TheDipBook #PortfolioLife #ModernElderAcademy #CarbonAlmanacProject #AltMBAJourney #RebrandingMidlife #CreativeAging #WisdomInMidlife #OpportunityCostLesson #EntrepreneurAfter50 #LifeAsArtProject #TeachingLegacy
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About 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.
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