How Intergenerational Living Creates Purpose & Joy | Marc Freedman
What if aging wasn’t about slowing down—but about leveling up?In this powerful conversation, Marc Freedman, founder of Encore.org (now CoGenerate), unpacks the surprising history of retirement, why communities like Sun City reshaped how we see aging, and how we can flip the script on what it means to grow older. From encore careers to intergenerational mentorship, Marc shows why midlife is no dead end—it’s a launchpad for purpose, impact, and connection.If you’ve ever wondered how to thrive after 50, find meaning in your “second act,” or simply stay relevant in a rapidly changing world, this episode will change how you see the road ahead.Timestamps:00:00 Intro00:39 Marc Freedman as Chip’s “modern elder”02:46 How aging became feared, not revered04:26 Why older people are no longer revered07:30 Rise of retirement communities13:14 Why people question retirement as a goal15:56 Marc’s personal view on retirement18:36 The origins & evolution of CoGenerate24:10 Why intergenerational connection matters27:46 What CoGenerate does to help31:52 Big policy ideas for the future37:31 Tips for those nearing retirement44:15 Upcoming workshop with Chip48:47 Wisdom bumper sticker50:51 How does Marc measure success54:00 Wrapping upLearn more about MEA at https://www.meawisdom.com/#MarcFreedman #EncoreCareers #ModernElder #MidlifeReinvention #FindingPurpose #LifeAfterRetirement #GenerationalCollaboration #CrossGenerational #AgingWell #WisdomAtWork #EncoreOrg #CoGenerate #ModernElderAcademy #SecondActCareers #PurposeDrivenLife
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Aging Boldly and Living on Your Own Terms with Karen Walrond
Author, speaker, and “Radiant Rebel” Karen Walrond joins Chip Conley for a warm, inspiring conversation on how to age with joy, live on your own terms, and keep your spark alive.From growing up between Trinidad and the U.S., to leaving engineering and law for a creative life, Karen’s story is full of bold choices and unexpected turns. She shares cultural insights on aging, how to break free from the “success script,” and the seven playful experiments from her new book In Defense of Dabbling that prove it’s never too late to try something new.Packed with heart, humor, and practical wisdom, this episode will leave you smiling and inspired to chase your own adventures.Timestamps:00:00 Intro00:45 Introduction to Karen Walrond01:58 Growing up & career journey06:50 Midlife shift toward writing and creative work11:38 Cultural perspectives on aging in Trinidad vs. the U.S.16:55 Defining the “Radiant Rebellion”19:14 Resisting societal scripts23:06 Aging in non-white cultures31:43 Collaboration with Brené Brown36:12 Introducing In Defense of Dabbling40:03 The 7 attributes of dabbling44:08 Why trying new things matters as we age50:42 Karen’s experience teaching at MEA workshops53:11 Karen’s wisdom bumper sticker57:10 Chips’s closing reflections on joy, culture, and lifelong learningLearn more about MEA at https://www.meawisdom.com/#AgingBoldly #MidlifeReinvention #RadiantRebellion #LifeOnYourOwnTerms #NeverTooLate #MidlifeTransformation #CuriosityAndPlay #JoyfulAging #BreakingFree #LiveFully #MidlifeMotivation #RedefiningSuccess #KeepYourSparkAlive #IntentionalLiving #TrySomethingNew
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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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How Sara Blakely Built Spanx and Found Her Next Big Purpose
What happens when a self-made billionaire steps away from the company she built and faces the big question: What’s next?In this inspiring episode, the founder of Spanx opens up about her journey from door-to-door sales to creating a global brand, the emotional challenges of selling her company, and how she’s redefining success, purpose, and identity in midlife. It’s a raw and uplifting conversation about reinvention, intuition, and finding meaning beyond business.Timestamps:00:00 Intro01:56 Family background and kids03:47 Childhood struggles and early mindset shift06:32 Discovering Wayne Dyer and self-growth09:00 Letting go of law school plans09:46 Intuition and coping mechanisms13:25 Selling fax machines and rethinking her path14:17 The idea for Spanx is born18:40 Building Spanx and landing Neiman Marcus22:37 Growing Spanx without advertising25:30 Selling Spanx and facing an identity shift31:51 Midlife change and grief34:44 Creating Sneaks brand43:54 Psychology behind the second venture47:32 Perimenopause, health issues, and PMDD50:19 Modern Elder Academy experience53:37 Focusing on presence and meaning55:42 Introverts, extroverts, and integration58:17 Feminine energy as a superpower59:42 Wisdom bumpersticker1:02:26 Chip’s final thoughtsLearn more about MEA at https://www.meawisdom.com/#SarahBlakely #Spanx #FemaleEntrepreneur #WomenInBusiness #EntrepreneurLife #BusinessSuccess #Motivation #Inspiration #FounderStory #StartupJourney #MindsetMatters #SuccessTips #BusinessAdvice #SelfMadeWoman #EntrepreneurMindset #ChipConley #MidlifeChrysalis
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What 50 Years with the Dalai Lama Taught About Midlife | Pico Iyer
What if midlife isn’t a breakdown—but a breakthrough?In this powerful conversation, world-renowned writer Pico Iyer shares the surprising lessons he’s learned from 50 years of friendship with the Dalai Lama, losing everything he owned, and finding stillness in the chaos. From walking away from success in New York to building a soulful life in Japan, Pico reveals how true freedom comes not from having more—but from letting go. This episode is a masterclass in finding purpose, inner peace, and meaning in the second half of life.Timestamps:00:00 Intro01:13 Meet Pico Iyer02:02 Why TED Keeps Inviting Pico Back02:50 Pico’s favorite TED talk04:04 Early Life Across Continents05:17 What “Home” Really Means07:21 Stillness and the Midlife Chrysalis12:33 Moving from Park Avenue to Kyoto15:31 The Value of Being an Expat18:10 Inner Calm in a Chaotic World22:31 Everyday Stillness Practices29:24 A Lifetime with the Dalai Lama37:34 Living in Absence of Answers42:29 Pico’s Anticipated Regret46:11 What Makes MEA So Special50:47 Awe, Community, and Transformation53:27 Pico’s Wisdom Bumper Sticker56:27 Episode Key TakeawaysLearn more about MEA at https://www.meawisdom.com/#MidlifeChrysalis #PicoIyer #ChipConley #MidlifeTransformation #ModernElder #Stillness #InnerWisdom #SpiritualGrowth #LifePurpose #DalaiLama #HomeAndSoul #ExpatLife #GratitudePractice #Resilience #MindfulLiving
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.
Ireland