The Midlife Chrysalis

Chip Conley
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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.

  1. 2 DAYS AGO

    Stop Living on Autopilot. Start Living for Real | Bonnie Wan

    Most people don’t realize they’re living someone else’s life until it’s too late. In this episode, Chip Conley sits down with Bonnie Wan, a renowned brand strategist and author of The Life Brief, who has spent decades studying human behavior, and now helps people redesign their lives with clarity and intention. Through her “Life Brief” method, people learn how to cut through the noise and make decisions that truly align with them. Key insights: Why clarity alone doesn’t change your lifeThe one question that reveals what you really wantHow to stop living on autopilotWhat’s really behind feeling stuck in midlife If something feels off but you can’t explain why, this will make it clear. Watch now and start taking your life back. Timestamps: (00:00) Intro and episode setup(04:04) Bonnie Wan introduction (04:44) Early life and path into advertising (07:47) The “Got Milk” story and key insight (13:05) What is The Life Brief (14:46) Clarity and “Fuck Yes” feeling (16:24) Why people feel stuck in midlife (17:10) Powerful questions to change your life (20:00) Marriage crisis and breakthrough (23:06) “Take Our Time” life brief (26:15) From career to calling (30:01) Ambition from the inside out (31:38) What gets better with age (33:09) What does “enough” really mean (35:43) Redefining wealth as relationships (36:11) Designing a slower, intentional life (40:25) “Chase your goosebumps” advice (41:56) Breaking free from the success script (47:40) Final reflections and closing Learn more about MEA at ⁠https://www.meawisdom.com/ #LifeBrief #BonnieWan #FindYourFuckYes #MidlifeClarity #LifeOnPurpose #StopLivingSomeoneElsesLife #LifeRedesign #ClarityInLife #MidlifeAwakening #IntentionalLiving #LifeStrategy #PersonalClarity #ReclaimYourLife #InnerKnowing #LifeReset

    52 min

  2. 4 DAYS AGO

    Knowledge Won’t Save You. Curiosity Will

    You don’t stay relevant by knowing more. You stay relevant by staying curious. In this episode of Wisdom Wednesday, Chip Conley joins Derek Gehl to break down why curiosity, not experience or intelligence, is the real edge in midlife and beyond. Here’s what stands out: Curiosity is the antidote to irrelevanceAsking better questions beats having the right answersMidlife requires a shift from knowledge to wisdomLearning for no reason can unlock new purposeStaying curious keeps your mind sharp and engaged It’s a simple shift, but it changes everything. 👉 Watch now and start thinking like a beginner again Timestamps: 00:00 Why curiosity improves work and life 03:34 Curiosity as antidote to irrelevance 06:18 Chip’s experience at Airbnb 10:10 Power of asking better questions 12:33 Curiosity vs learning explained 14:46 Curiosity and innovation culture 18:04 Learning for curiosity not productivity 18:48 Turning curiosity into new paths 22:45 How curiosity looks for everyday people 25:51 Learning for the sake of passion 26:56 Lifelong learning and aging 28:38 Curiosity and brain health 29:07 Key question what are you a beginner in 30:12 Creating space for curiosity Learn more about MEA at ⁠https://www.meawisdom.com/ #curiosity #growthmindset #lifelonglearning #midlifegrowth #selfimprovement #personaldevelopment #mentalfitness #stayrelevant #learnhowtolearn #askbetterquestions #mindsetshift #reinventyourself #emotionalintelligence #careertransition #wisdom

    28 min

  3. 6 DAYS AGO

    She Quit a 30-Year Career to Help Others Rebrand Their Lives | Robin Fisher Roffer

    Midlife might be the moment everything finally starts to make sense. In this episode of The Midlife Chrysalis, Chip sits down with branding expert Robin Fisher Roffer, who spent over 30 years shaping major brands, to explore how those same principles can help you reinvent your life. Robin shares her own powerful transition, stepping away from a successful career to start a whole new chapter, and what she’s learned along the way. In this episode, you’ll discover: Why real change starts by reconnecting with your original storyThe 3 essentials of a strong personal identity: clarity, consistency, and authenticityHow to define your own “tagline” for your next chapterA refreshing way to see midlife as freedom, finally If you’re feeling ready for something new, or just a little more you, this one will stay with you. 👉 Watch now and take the first step toward your next chapter. Timestamps: 03:44 Father’s influence and childhood story 06:55 Early exposure to advertising 08:12 Career path and starting agency 09:56 Brand strategy principles explained 13:34 Intuition and big ideas in branding 16:34 Applying branding to personal identity 18:33 Workshop transformations and examples 20:04 Fast decision-making and creativity 21:59 Rebranding midlife discussion 24:50 Taglines and brand positioning 27:28 Personal midlife transformation 32:26 Moving to Santa Fe and lifestyle 34:48 Wisdom bumper sticker 39:21 Workshop experience and benefits Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeReinvention #RebrandYourLife #StartOverAt60 #LifeAfter50 #PersonalBranding #FindYourPurpose #CareerChange #NextChapter #SelfReinvention #WomenOver50 #LifeTransformation #PersonalGrowth #SecondAct #MeaningfulLife #MidlifeChrysalis

    46 min

  4. 10 APR

    Feeling Lost? Use Inner Tracking to Find Your Path| Lee Johnson

    Midlife can feel confusing, off track, or quietly unsettled, and you’re not the only one feeling it.  In this episode of Midlife Chrysalis, Lee Johnson, a mindfulness guide and teacher, shares his journey from ranch life to guiding others through mindfulness and “inner tracking,” offering a grounded and deeply human perspective on finding your way without a clear plan.  Here’s what you’ll take away: • Why feeling lost in midlife is often a turning point, not a problem • What inner tracking is and how it helps you make aligned decisions • How to trust your path even when nothing feels certain • Why disconnection is so common and how to reconnect with yourself • A simple awareness practice you can use right away  If midlife has you questioning your direction, this conversation will bring clarity and calm. Watch now and start finding your way back.  Timestamps: 00:00 Introduction and welcome 00:22 Lee Johnson’s origin story 01:10 Early influences and spiritual mentors 02:56 Energetic imprint and childhood experiences 04:00 Alaska years and connection to nature 05:30 Holistic health and yoga ashram journey 07:09 Life at Kripalu and spiritual growth 08:30 Native American teachings and Vipassana 09:57 Regenerative agriculture and land philosophy 12:09 Leaving the ranch and searching for purpose 14:24 Joining the ranch and new beginnings 17:17 Transition to teaching and inner work 19:53 Self-doubt and stepping into leadership 21:24 Discovering guided meditation and teaching 22:53 Inner tracking explained 27:37 Intuition and life path insights 30:23 “I don’t know where I’m going…” 31:33 Observations on midlife transformation 35:28 Disconnection and modern life 38:55 Guided inner tracking exercise 44:03 Workshops and teaching approach 47:29 Collaboration with partner Melanie 48:26 Life advice and awareness practice 52:57 Turning wounds into wisdom  Learn more about MEA at ⁠https://www.meawisdom.com/  #MidlifeChrysalis #MidlifeTransformation #FindYourPurpose #LifeTransitions #InnerWork #MindfulnessPractice #PersonalGrowth #MidlifeJourney #SelfDiscovery #EmotionalWellbeing #LifeDirection #SpiritualGrowth #ReconnectWithYourself #InnerPeace #PurposeInMidlife

    1hr 2min

  5. 8 APR

    Stuck Between Aging Parents and Grown Kids in Midlife?

    You’re taking care of your parents. You’re supporting your kids. But who’s taking care of you? In this Wisdom Wednesday episode, Derek Gehl sits down with Chip Conley to unpack the reality of the sandwich generation and why midlife can feel more overwhelming than ever.  Chip shares key insights on: • The real emotional cost of caregiving • Why this stage of life feels heavier today • How to build a support system that actually helps • Why protecting time for yourself is essential A clear, honest conversation for anyone feeling stretched thin in midlife. 👉 Watch the full episode and subscribe for more real conversations like this.  Timestamps: 00:20 The sandwich generation 01:24 Chip’s caregiving experience 02:49 Importance of support system 04:25 Emotional toll of caregiving 07:31 Having kids later in life 09:27 Adult kids moving back home 10:27 Longevity and caregiving challenges 12:56 Health span vs. lifespan 15:12 Independence and interdependence 16:50 Longevity manifesto explained 18:06 Science vs art of longevity 19:03 Blue Zones lifestyle insight 20:18 Caregiver workshop challenge  Learn more about MEA at ⁠https://www.meawisdom.com/  #SandwichGeneration #MidlifeStruggles #Caregiving #AgingParents #MidlifeCrisis #CaregiverLife #EmotionalBurnout #FamilyCare #Longevity #Healthspan #MidlifeSupport #PersonalGrowth #StressManagement #LifeTransitions #ChipConley

    19 min

  6. 6 APR

    Leading in Chaos: How to Stay Grounded Under Pressure | Amy Elizabeth Fox

    What if the chaos in your life isn’t the problem… but the turning point? In this episode, Amy Elizabeth Fox, leadership expert and co-founder of Mobius, explains why today’s pressure, uncertainty, and stress are actually pushing us to grow in a deeper way. Through her work with top executives and her own life story, she shows what it really takes to lead and stay grounded when everything feels unstable. Here’s what you’ll learn: Why people fall back into old patterns under stressHow your past shapes the way you lead and live todayWhy success in midlife can feel empty and how to change thatWhat it really means to lead in chaosWhy healing and self-awareness matter more than ever This is not just about leadership. It’s about understanding yourself on a deeper level. 👉 Watch now if you feel overwhelmed, stuck, or ready for something more. Timestamps: 2:43 What is vertical development 4:10 Personal and professional growth merge 5:29 Midlife leadership struggles 8:24 Early life challenges and illness 10:37 Genetic disease and urgency 11:35 Spiritual and environmental work 13:21 Leadership and spirituality connection 15:35 Corporate transformation and culture 19:29 Freedom after adversity 21:08 Feminine leadership in business 22:55 Leading in chaos introduction 24:40 Spiritual path and teachers 27:03 Spirituality in action 28:42 Chaos and leadership today 31:51 Key principles for leading in chaos 35:00 Corporate reality and hope 37:38 Midlife transformation insights 40:25 What improves with age 41:59 Freedom in midlife 46:28 From receiving to giving 47:24 Final wisdom and life philosophy ABOUT AMY ELIZABETH FOX: Bio: Amy Elizabeth Fox is the co-founder and CEO of Mobius Executive Leadership, a global transformational leadership firm. For over twenty years, she has advised senior leaders in eminent professional services firms and Fortune 500 companies on leadership and culture change. In 2026, she co-authored Leading in Chaos with Nicholas Janni and is widely regarded as an expert in vertical development and trauma-informed work in organizations. Read the Full Bio Links: Leading in Chaos Book Website: https://leadinginchaosbook.com/ Mobius Website: http://www.mobiusleadership.com/ Amy’s Website: http://www.amyelizabethfox.com/ ABOUT LEADING IN CHAOS Book Overview: Nicholas Janni and Amy Elizabeth Fox’s forthcoming book, Leading in Chaos, argues that in an era of polycrisis and sustained uncertainty, leadership requires next practice — a fundamentally different inner operating system grounded in deeper human intelligence. It reframes leadership as an embodied, developmental practice, calling leaders to act with coherence, presence, and integrity amid ongoing disruption. Because, in their words, “chaos is the new black.” Social media posts: LinkedIn postInstagramFacebook Learn more about MEA at ⁠https://www.meawisdom.com/ #Leadership #LeadingInChaos #PersonalGrowth #SelfAwareness #EmotionalIntelligence #MidlifeGrowth #BurnoutRecovery #StressManagement #InnerWork #HighPerformance #MindsetShift #ExecutiveLeadership #PsychologyOfSuccess #WorkplaceCulture #LeadershipDevelopment

    56 min

  7. 3 APR

    She Told 80,000 Employees the Truth She Hid Her Entire Life | Katherine Dudtschak

    She had the perfect life - career, family, success - and a secret she kept hidden for decades. In this episode, Katherine Dudtschak, a former top banking executive, opens up about coming out at 50, telling 80,000 employees, and risking everything to finally live in alignment with who she truly is.It’s an honest, deeply human story about what happens when you spend years living the life you’re “supposed” to live, and what it takes to finally choose your own.  You’ll hear: Why even a “perfect” life can feel incompleteHow suppressed identity shows up over timeThe moment everything became impossible to ignoreWhat it really takes to start over without losing yourselfWhy vulnerability can become your greatest strength👉Watch now! It’s never too late to choose yourself.  Timestamps: 2:02 Katie’s background and corporate success 3:36 Feeling incomplete despite success 5:24 Childhood struggles and proving herself 7:44 Midlife awakening begins 9:07 Family history and trauma 12:31 Suppressed identity resurfaces 15:28 Career success but emotional collapse 17:53 Defining gender identity moment 20:57 Mental health crisis and turning point 21:36 Commitment to truth and coming out 23:21 Coming out to 80,000 employees 27:38 Team reaction and support 28:42 Unexpected outcome and acceptance 29:24 Advice on major life changes 31:48 Power of vulnerability 33:09 Building the right support system 36:25 Importance of time and process 38:48 Career transition and new identity 41:52 New purpose and leadership vision 43:48 CEO role and serving older adults 46:20 Launching Sincerely and storytelling mission 49:12 Vision for a more human world 52:22 Core message reclaim your essence 54:37 The three selves explained Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeTransformation #ComingOutStory #LifeAfter50 #FindYourself #AuthenticLiving #GenderIdentity #PersonalGrowth #LifeChange #MentalHealthJourney #StartOver #BeYourself #SelfDiscovery #LGBTQStories #EmotionalHealing #PurposeDrivenLife

    1hr 1min

  8. 1 APR

    Why So Many Men Lose Friends in Midlife (And How to Fix It)

    What if the biggest factor for a longer, happier life isn’t health, but friendship? In this Wisdom Wednesday episode, Chip Conley joins Derek Gehl to explore why so many people, especially men, struggle with connection in midlife, and how to change that. Here’s what you’ll learn: Why friendship is the #1 predictor of longevityThe difference between real vs transactional relationshipsWhy men often lack deep connection and how to fix itThe one simple habit that can reignite old friendships If you’ve been feeling disconnected, this conversation will resonate more than you expect. 👉 Watch now and reconnect with what really matters Timestamps: 00:00 Intro and Yellowstone ranch vibe 01:24 Building the ranch experience 03:07 Why connection matters for longevity 04:09 Why men struggle with friendships 06:32 Why are women more drawn to workshops 08:32 Transactional vs real friendships 12:07 Vulnerability and male friendship barriers 13:51 Story about father finding community later in life 14:55 Friendship and regrets at the end of life 16:38 Marriage pressure and need for male friendships 17:59 Friendship as a daily practice 18:46 Introverts vs extroverts and connection 19:50 Simple action to rebuild friendships 20:24 Workshops and final takeaway Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeCrisis #FriendshipMatters #MensMentalHealth #Loneliness #MidlifeMen #SocialConnection #SelfDevelopment #EmotionalHealth #MentalWellbeing #BuildBetterRelationships #PersonalGrowth #LifeInMidlife #ConnectionMatters #ModernElder #HealthyRelationships

    19 min
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About

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.

Information

  • Creator
    Chip Conley
  • Years Active
    2025 - 2026
  • Episodes
    96
  • Rating
    Explicit
  • Copyright
    © Chip Conley
  • Show Website
    The Midlife Chrysalis

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