The Midlife Chrysalis

Chip Conley
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Aug 13, 2025 • 58min

Martha Beck on Psychic Gifts, Polyamory, and Finding Purpose

What happens when a Harvard scholar, devoted Mormon, and mother of a child with Down syndrome begins to hear psychic messages—and decides to tell the truth no matter the cost?In this powerful conversation, Martha Beck shares how leaving her religion, embracing polyamory, and facing her deepest fears led her to a life of radical integrity, joy, and healing.If you’ve ever felt stuck, out of alignment, or afraid to be fully yourself—this episode will change how you see everything.Timestamps:00:00 Intro00:56 Meet Martha Beck03:02 Growing Up Mormon, Academic Journey, and Her Son’s Diagnosis10:53 Leaving Mormon Church & Reframing Midlife14:47 Losing Religion, Finding Soul, and Polyamory19:20 Returning to True Nature Through Rebellion21:23 Lessons from Her Son with Down Syndrome27:10 Psycho-Neuro-Immunology & Integrity30:58 Shaman Sickness & Becoming a Healer33:24 A Simple Path to Inner Stillness40:01 The Radical Power of Not Lying41:43 How to Listen to Your Body’s Response52:27 Martha’s Bumper Sticker WisdomLearn more about MEA at ⁠https://www.meawisdom.com/#MarthaBeck #ChipConley #TheWayOfIntegrity #MidlifeTransformation #SpiritualAwakening #LeavingMormonism #DownSyndromeParenting #PolyamoryJourney #LifePurpose #InnerHealing #TrustYourself #ModernElder #SelfDiscovery #PsychicExperiences #AnxietyAwareness
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Aug 6, 2025 • 1h 6min

How Sara Blakely Built Spanx and Found Her Next Big Purpose

Sara Blakely, the founder of Spanx, shares her entrepreneurial journey from selling fax machines to creating a billion-dollar brand. She discusses the emotional challenges of selling Spanx and her identity shift in midlife. Blakely emphasizes the importance of intuition, vulnerability, and redefining success beyond business. She also dives into her new venture, Sneaks, blending style and comfort in footwear. Her insights on growth, resilience, and embracing one's feminine energy make for an inspiring conversation about navigating personal transformations.
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Jul 30, 2025 • 59min

What 50 Years with the Dalai Lama Taught About Midlife | Pico Iyer

In this enlightening conversation, Pico Iyer, a celebrated writer and long-time friend of the Dalai Lama, shares invaluable insights from their 50-year friendship. He explores the concept of midlife as a breakthrough rather than a breakdown, emphasizing the importance of letting go to find true freedom. Pico discusses his transformative move from New York to Kyoto, the significance of stillness, and practical mindfulness tips. He reflects on the wisdom gleaned from life's contradictions and the urgency of living fully as we age.
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Jul 23, 2025 • 59min

From Famous Father to Finding Purpose: Scott Eastwood at Midlife

What happens when a successful actor—and the son of a Hollywood legend—hits midlife and starts asking deeper questions?In this powerful episode, Scott Eastwood opens up about building his own identity beyond Clint Eastwood’s shadow, what 40+ films have taught him, and why he’s now prioritizing purpose over fame. He reflects on masculinity, mentorship, mistakes, and what it really means to grow wiser with age.What happens when a successful actor—and the son of a Hollywood legend—hits midlife and starts asking deeper questions?In this powerful episode, Scott Eastwood opens up about building his own identity beyond Clint Eastwood’s shadow, what 40+ films have taught him, and why he’s now prioritizing purpose over fame. He reflects on masculinity, mentorship, mistakes, and what it really means to grow wiser with age.Feeling your own shift? Subscribe to The Midlife Chrysalis and explore Modern Elder Academy’s workshops designed to help you thrive in midlife and beyond.Timestamps:00:00 Intro00:41 Chip’s Relationship With His Dad 08:28 A Prolific Film Career09:38 Working with Clint Eastwood10:51 Carving His Own Path13:54 New Projects & Genre Exploration15:52 Masculinity in Modern Culture18:09 Growing & Maturing as a Man19:26 Questioning & Redefining Midlife21:32 Childhood Dreams & Creative Shifts24:05 Aging, Directing & Creative Control27:1 Time, Regret & Following Your Gut31:51 The Outpost Movie & Hyperbaric Healing35:07 Real Wellness, Not Wellness Trends37:16 Life Lessons & Emotional Maturity39:44 How Scott Hopes to Be Remembered41:31 Lessons from Mom & Dad43:20 Having Mentors & Becoming One44:13 Scott’s Wisdom Bumper Sticker49:13 Healing a Father-Son RelationshipLearn more about MEA at ⁠https://www.meawisdom.com/#ScottEastwood #MidlifeChrysalis #ChipConley #ClintEastwood #MasculinityToday #ActorLife #FilmIndustry #PersonalGrowth #LegacyAndIdentity #MidlifeReflection #LifeLessons #EmotionalMaturity #CreativeJourney #WellnessWisdom #FollowYourGut
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Jul 16, 2025 • 59min

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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Jul 10, 2025 • 57min

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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Jul 2, 2025 • 58min

Psychedelics, Purpose & the Next Chapter of John Mackey’s Life

John Mackey, the visionary founder of Whole Foods Market and advocate for conscious capitalism, shares his journey of reinvention at 69. He delves into transformative experiences with psychedelics that led to profound spiritual breakthroughs. Mackey discusses the evolution of conscious capitalism and why love is the ultimate business strategy. He opens up about his transition from leadership at Whole Foods, the challenges of building Love Life wellness centers, and how embracing purpose can redefine retirement and longevity.
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Jun 25, 2025 • 1h 5min

Rich Roll on Reinventing Yourself After Rock Bottom

In this inspiring conversation, Rich Roll, a former addict turned world-class endurance athlete and podcaster, shares his remarkable journey of transformation. He discusses hitting rock bottom and how it led him to find true purpose through sobriety and plant-based nutrition. Rich reflects on the importance of vulnerability, rejecting societal pressures, and the power of genuine connections. He also delves into his transition from writing to podcasting and emphasizes the value of service in uncovering new opportunities for personal growth.
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6 snips
Jun 18, 2025 • 53min

Reinvention After 50 with Seth Godin: Make Life Your Best Work of Art

Seth Godin, bestselling author and entrepreneur renowned for his marketing insights, shares his transformative views on midlife. He argues that this stage can be a creative renaissance rather than a crisis. Topics include the significance of 'the dip' in personal growth, the importance of aligning work with one's values, and the potential for reinvention. Seth encourages embracing aging as an opportunity for legacy-building and emphasizes the power of creativity in shaping a fulfilling life beyond 50.
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Jun 11, 2025 • 46min

You Can’t Scare Me: Hoda Kotb on Starting Over and Fearless Living After 50

Hoda Kotb, a celebrated journalist and author, shares her inspiring journey of resilience and reinvention after turning 40. She candidly discusses overcoming breast cancer, navigating a tumultuous marriage, and finding joy through adoption at 52. Hoda highlights the power of starting over and embracing new experiences in one’s 50s and 60s. Her reflections on love, motherhood, and the mindset of lifelong learning encourage listeners to face life's challenges with courage and gratitude.

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