The Midlife Chrysalis

What if losing everything was the only way to truly find yourself?MIT lecturer and artist Aithan Shapira shares how the collapse of his art career became the catalyst for profound reinvention. He explains why midlife isn’t about decline but transformation , a time to practice letting go, reframe purpose, and reconnect with what matters most. If you’re in a season of change, this episode will help you see midlife as your greatest canvas yet. Timestamps:00:00 Intro01:17  Meet Aithan Shapira04:05 Living Between Worlds05:32 MIT, NASA & Global Clients06:32 Practice as a Core Principle07:46 Cubism & Midlife Transition11:00 Life as a Practice vs Routine14:05 Practice vs. Ritual15:30 Aithan’s Views on Midlife20:55 Accelerating Internal Change25:37 The Three Stages of Transition27:59 Coping With Freefall32:59 What Needs to Be Preserved36:11 Identity in Retirement & Second Half of Life38:18 Aithan’s Own Chrysalis Story46:21 Long Life Learning53:21 The Wisdom of Midlife55:58 Aithan’s Bumper Sticker Wisdom59:07 Closing Thoughts Learn more about MEA at ⁠https://www.meawisdom.com/

What if midlife isn’t the end of your career story but the smartest place to rewrite it? In this episode of Wisdom Wednesday, Chip Conley joins Derek Ghal to unpack what really happens when people feel stuck at midlife, and why career change after 50 doesn’t require starting over or burning everything down. Drawing on his journey from boutique hotels to Airbnb to founding the Modern Elder Academy, Chip offers a grounded, hopeful roadmap for reinvention that actually works in the real world. In this episode, you’ll learn:Why midlife can be the most strategic time to change careers, not the riskiestHow to use small, iterative steps and bridge jobs instead of all-or-nothing leapsThe four pathways to purpose that reveal what’s next for youWhy portfolio careers and encore paths are becoming the new normalHow identity, fear, and “being a beginner again” shape midlife transitions If you’re questioning your work, your direction, or what the next chapter should look like, this conversation will help you reframe what’s possible. Watch the episode, reflect on what’s calling you next, and take the first small step forward. Timestamps:00:41 Chip Conley’s career journey03:10 Rethinking age and career length05:23 Retirement vs staying relevant10:43 Taking small iterative steps13:25 Entrepreneurship after 5016:33 Bridge jobs and testing ideas18:26 A real midlife pivot story19:18 Purpose, community and wellness23:29 Identity fear and becoming a beginner27:17 Why people come to MEA31:47 Final thoughts and wrap-up Learn more about MEA at ⁠https://www.meawisdom.com/

He had everything going for him, until his body shut him down on live TV.In this episode, Dan Harris sits down with Chip Conley for a warm, honest conversation about ambition, anxiety, and what really changes in midlife. Dan opens up about the panic attack that forced him to slow down, his years inside high-pressure newsrooms at ABC, and the quiet realization that productivity, without presence, was costing him more than it gave. What follows is not a polished mindfulness pitch, but a deeply human reflection on letting go, growing wiser, and redefining success in the second half of life. In this conversation, you’ll hear Dan reflect on:Why anxiety and ambition are often two sides of the same coinHow meditation helped him step out of the productivity trap—not optimize itWhat he had to release after becoming outwardly “successful”Why midlife is better understood as a chrysalis, not a crisisHow relationships, presence, and character shape a more meaningful future If you’re navigating midlife, questioning old definitions of success, or simply craving a more spacious way to live, this conversation will feel like sitting down with two thoughtful friends who’ve been there. Watch now and join the conversation. Timestamps:02:17 Defining midlife and Dan Harris’s journey03:50 Panic attack on live TV05:31 From panic attack to meditation06:46 Family background and anxiety08:31 Decade between crisis and mindfulness advocacy09:33 Therapy spirituality and discovering meditation13:37 Writing 10% Happier14:22 Origin of the 10% happier idea16:43 Science and benefits of meditation19:47 Skepticism identity and cognitive dissonance22:14 Life after the book’s success26:06 Productivity versus presence29:47 Burnout hyper productivity and 360 review33:06 Letting go of roles and redefining life35:59 Midlife as chrysalis not crisis39:36 Favorite meditation practices42:09 Wisdom midlife and modern elderhood45:08 Character skills in the age of AI47:07 Personal wisdom and life lessons49:10 Closing reflections and goodbye Learn more about MEA at ⁠https://www.meawisdom.com/

Cancer doesn’t just affect your health. It changes how you see yourself and your life. In this warm and honest conversation, Chip Conley sits down with Caryn Lerman to explore the emotional side of cancer that often goes unspoken. Together, they talk about identity shifts, caregiving, and what it really means to move through the messy middle of midlife after a diagnosis. In this episode, you’ll hear:How cancer reshapes identity, not just the bodyWhy caregivers carry an invisible emotional loadWhat it means to live intentionally after cancerHow vulnerability can become a source of strengthWatch the full episode and join us for a thoughtful, compassionate conversation about healing, meaning, and becoming who you are now. Timestamps:04:14 Psychology of cancer survivors and caregivers06:47 Identity loss and existential impact of cancer07:53 Chip’s cancer diagnosis and early denial13:13 Regret fear, and emotional processing16:23 Cancer as a teacher and life priorities19:39 Anxiety treatment and living with uncertainty20:33 Staying busy to avoid difficult emotions24:16 Values family and vulnerability26:01 Strength identity and emotional suppression28:01 Caregivers and lack of support systems30:10 Invisible burden of caregiving32:06 Emotional catharsis and healing journey35:32 Caregiver and survivor archetypes38:49 Inside the cancer thrivers workshop42:18 Identity mapping and letting go43:41 Meaning values and intentional living45:42 How friends can best support someone with cancer47:26 Cancer is not a linear journey48:28 Wisdom bumper sticker advice51:53 Growth outside the comfort zone Learn more about MEA at https://www.meawisdom.com/

What if the way you start your morning is quietly shaping how your whole day feels?Chip Conley sits down with Derek Gehl to explore why so many midlife routines start to feel empty and how turning them into simple, meaningful rituals can bring more calm, clarity, and purpose to everyday life. Together, Chip and Derek share:Why routines can feel mechanical, while rituals help us feel present and changedHow to gently layer meaning onto things you already do, like showering or stretchingWhy small morning rituals can boost mood, energy, and emotional well-beingHow affirmations work best when they’re personal, specific, and emotionally realEasy ways to create micro-rituals that set a better tone for your day If midlife has you longing for more intention without adding more to your plate, this episode is a friendly invitation to start small and start with your morning.Give it a listen, try one simple ritual this week, and notice what begins to shift. Timestamps:02:12 Morning rituals vs routines02:28 Routine vs ritual04:00 Shower meditation prayers05:48 Affirmations and new stretching ritual11:21 The impact of morning rituals12:27 Accountability and consistency14:01 Rituals as landmarks and micro rituals15:24 How to create your own rituals17:07 Science and specificity of affirmations Learn more about MEA at ⁠https://www.meawisdom.com/

In this episode, Chip Conley sits down with Christine Sperber, co-founder of MEA and master experience designer, to explore how awe, ritual, and community can bring us back to life in midlife. Drawing from ski town culture, life in Baja, and years of building transformational experiences, Christine offers a hopeful reframe of aging as something to design, not fix.In this conversation, Chip and Christine explore:Why purpose matters more than productivity in midlifeHow simple rituals create meaning, resilience, and belongingWhat nature, movement, and community teach us about vitalityWhy transitions like perimenopause and loss call for compassion, not hustleIf midlife feels like a pause, a question mark, or an invitation to something more, this episode will leave you feeling seen, grounded, and hopeful.Listen now and rediscover what it means to feel fully alive in midlife. Timestamps:03:22 Christine Sperber’s background06:55 Leaving Colorado for Baja08:49 First experience of Baja and Pescadero10:59 Freedom and living in rhythm with nature15:15 Experience design and creating meaningful gatherings17:48 Baking bread as ritual and collective practice22:14 Origin story of MEA24:02 Early doubts and building a local economy26:07 Lessons from the first MEA beta cohorts30:38 Ski towns, purpose, and longevity research33:46 Aging, vitality, and midlife perspective40:49 Introversion, ritual, and reclaiming time46:19 Third vault conversations and authentic community48:26 Moral beauty as a pathway to awe54:11 Transformation through deep connection56:19 Designing belonging and social bonds57:28 Wisdom bumper stickerLearn more about MEA at ⁠https://www.meawisdom.com/ 

Midlife isn’t the end of the story, it’s the chapter where something new wants to begin.In this episode of Midlife Chrysalis, Chip Conley sits down with Pam McLean, pioneering coach, co-founder of the Hudson Institute of Coaching, and a guiding voice on adult development and the “bonus years.” Together, they explore why midlife isn’t about stepping back, but about letting go and moving forward with intention.Pam shares:Why releasing old identities is essential for growthWhat the “bonus years” make possible at any ageHow Life Forward helps reframe change as opportunityWhy discomfort, grief, and curiosity are part of becomingWhat truly makes a great coach — in life and in leadershipThis is a warm, thoughtful conversation for anyone standing at a crossroads and wondering what comes next. Watch now and discover how midlife can become a powerful new beginning. Timestamps:03:32 Pam’s early life and background04:17 From clinical psychology to coaching07:06 How coaching has developed09:31 Life Forward and Hudson Institute11:46 The midlife happiness curve14:53 Cancer as a life teacher16:06 Hudson Institute and MEA connection18:08 Letting go of old identities21:50 Navigating major life transitions26:27 Why experimentation matters27:39 Men vs women in midlife31:01 What makes a great coach33:47 Why people choose coaching35:15 Gender balance in coaching35:51 Coaching in the age of AI38:20 How to choose the right coach40:38 Creativity later in life42:41 Wisdom bumper sticker Learn more about MEA at ⁠https://www.meawisdom.com/

Midlife isn’t falling apart. It’s asking for your attention.In this episode of Midlife Chrysalis, Chip Conley dismantles the idea of the “midlife crisis” and replaces it with a far more hopeful and powerful framework: midlife as a chrysalis, a necessary transition into a second adulthood. Drawing from social science, psychology, and his own deeply personal story, Chip explains why midlife often feels like a breakdown, why it’s actually normal, and how it can become the most meaningful chapter of your life. In this conversation, you’ll discover:- Why happiness dips in midlife and rises afterward- How identity loss and burnout are signals, not failures- Why midlife hits men and women differently- How wisdom and purpose often peak later in life If you’re feeling burned out, disoriented, or quietly wondering, “Is this all there is?”, the answer, as Chip shows, is no. This is where something new begins.👉 Watch now to understand what midlife is really asking of you and how to move from breakdown to transformation. Timestamps:01:20 The Origin of the Midlife Crisis Idea04:40 The U Curve of Happiness06:21 Why Midlife Is Not a Crisis09:12 Becoming a Modern Elder11:24 Chip’s Midlife Struggles21:11 Why Midlife Lacks Support Systems23:17 Biology vs Life Circumstances25:49 How to Move from Crisis to Chrysalis30:23 Watching People Self-Destruct in Midlife34:18 Rebranding Midlife for the Future Learn more about MEA at ⁠https://www.meawisdom.com/#MidlifeCrisis #MidlifeTransformation #SecondAdulthood #MidlifeWisdom #MidlifePurpose #ModernElder #MidlifeBurnout #HappinessCurve #LifeTransitions #MidlifePodcast #AgingWell #PersonalGrowth #MidlifeReset #LifeAfter40 #FindingPurpose

What happens when ambition slows down, and wisdom begins to lead? Chip Conley, founder of Modern Elder Academy and host of Midlife Chrysalis, sits down with California Governor Gavin Newsom for a rare, deeply personal conversation shaped by nearly 30 years of mentorship and friendship. This is not a political interview, it’s an honest exploration of midlife, identity, and becoming.Together, they reflect on:How Gavin’s upbringing and dyslexia shaped his leadershipWhy legalizing same-sex marriage became a defining moral momentWhat the “winter years” between mayor and governor revealedHow fatherhood and midlife reshaped his relationship with powerWhy grace, humility, and resilience matter now more than everWarm, thoughtful, and deeply human, this episode explores what’s possible when we slow down and listen. If you’re navigating change or reinvention, watch now and step into the chrysalis.Timestamps:03:26 Welcome to Midlife Chrysalis04:06 Long friendship and early mentorship05:54 Childhood and family background08:48 Gavin’s writing experience16:03 Becoming mayor of San Francisco17:38 Decision to legalize gay marriage25:11 Impact of marriage equality27:54 Political winter as lieutenant governor29:24 Identity loss and slowing down33:21 Humility and leadership lessons35:22 Grace humility after years of division38:46 The lost art of civil disagreement41:49 Political vision and building bridges44:10 Stoicism and wisdom traditions47:44 Fatherhood and authenticity49:27 Wisdom bumper stickerLearn more about MEA at ⁠https://www.meawisdom.com/

What happens when success stops working and midlife hits hard?Blake Mycoskie, founder of TOMS Shoes, shares the story behind his most difficult chapter. After building a global brand and achieving massive success, Blake found himself facing a deep midlife reckoning marked by depression, loss of identity, and an urgent search for meaning beyond achievement.Blake opens up about:- How selling part of TOMS triggered an unexpected identity collapse- Why midlife depression often follows success, not failure- The treatments and inner work that helped him recover, including ketamine therapy and TMS- The simple but life-changing realization that shifted everything: “I am enough”- Why connection and community matter more than success or status👉 Watch now to hear Blake Mycoskie’s most vulnerable and meaningful story yet. Timestamps:01:11 Blake’s early entrepreneur journey02:49 Reality Central and first major failure04:59 The business lesson that shaped TOMS07:49 Creating the one for one model08:43 Selling TOMS and losing identity12:36 Depression behind the public image16:23 Searching for relief outside himself17:24 Medication fog and deep isolation19:30 Why telling others saved his life20:54 Moving beyond traditional medication21:12 Ketamine and TMS25:53 Discovering the core wound28:49 India and lasting inner freedom33:27 Launching the Enough initiative35:58 I’m Enough ritual poem37:57 How the nonprofit model works38:47 The growing mental health crisis43:13 Self compassion and flow state46:28 How to support someone in depression51:54 Living with fear of relapse54:17 Wisdom bumper sticker Learn more about MEA at ⁠https://www.meawisdom.com/#BlakeMycoskie #MidlifeCrisis #MentalHealthAwareness #EntrepreneurMentalHealth #SuccessAndDepression #TOMSFounder #MidlifeJourney #DepressionRecovery #FindingPurpose #SelfWorth #MentalHealthPodcast #MidlifeTransformation #HealingJourney #MenAndMentalHealth #IAmEnough

What if aging alone isn’t the only option?As midlife reshapes relationships, identity, and housing, a bold question emerges: what if women chose community instead of solitude?In this Wisdom Wednesday episode, Chip Conley, founder of Modern Elder Academy, joins Derek Gehl to explore the early-stage idea behind Golden Girls–style living, an intentional housing experiment he’s beginning in Santa Fe to address loneliness, gray divorce, and the realities of solo aging.In this episode, you’ll learn:- Why more women are aging solo in midlife- Why social connection matters more than health hacks- How housing no longer fits modern midlife needs- What Golden Girls–style living could look like in practiceThis isn’t a finished solution — it’s a timely experiment that reimagines how we live and age.👉 Watch now and decide if community belongs in your next chapter. Timestamps:02:40 Golden Girls homes concept03:41 Gray divorce and solo agers06:20 Loneliness and housing mismatch08:05 Why Golden Girls homes now10:10 The Santa Fe pilot homes12:49 Workshops and community vision15:29 What the research revealed18:14 Matching roommates and house culture21:10 Affordability and rental model24:10 What about men26:36 Long term vision and legacy29:21 How to get involved29:55 Final reflections Learn more about MEA at ⁠https://www.meawisdom.com/#MidlifeChrysalis #GoldenGirlsHomes #MidlifeTransition #SoloAgers #GrayDivorce #LonelinessEpidemic #IntentionalLiving #MidlifeCommunity #WomenOver50 #AgingWell #CommunityLiving #ModernElders #MidlifeWisdom #HousingInnovation #SocialConnection

Aging in America has never been the same for everyone. Chip Conley sits down with Ray Jetson, pastor, former Louisiana legislator, and author of Aging While Black, to explore why aging isn’t a race-neutral experience and what it really means to age well in a system that was never built for everyone.Ray shares a simple, powerful way to rethink aging through community, innovation, and shared wisdom across generations.In this episode, you’ll learn:Why aging while Black carries unique structural and economic realitiesHow the village concept and Sankofa help bridge past, present, and futureWhy technology and mutual mentorship matter for aging wellWhat collective longevity looks like across generationsThis conversation invites us to rethink aging, equity, and how we care for one another at every stage of life. Watch now and join the conversation. Timestamps:03:02 Three pillars of aging while black05:43 The village concept and African origins08:18 Ubuntu and community identity11:11 The Black church as a village13:07 Embracing innovation and technology18:39 Sankofa and learning from the past24:38 Intergenerational circles and family wisdom27:35 Collective longevity across generations33:08 Keeping hopeful and building systems39:50 Sources of inspiration and leadership43:20 What makes aging while black different51:03 Wisdom bumper sticker53:27 Closing thoughts and workshop invitation Learn more about MEA at ⁠https://www.meawisdom.com/

Most leaders are chasing short-term wins and missing the long game.In this episode, Chip Conley talks with Rand Stagen, founder of the Stagen Leadership Academy, about what’s quietly breaking leadership today and how to lead with purpose, perspective, and staying power.Rand shares hard-earned insights from decades of working with CEOs and entrepreneurs who want more than success, they want meaning.You’ll learn:- Why short-term thinking undermines great leadership- What it means to play the infinite game- How awareness creates better choices- Why the best leaders think in decades, not quartersIf you’re leading others, or rethinking your own direction, this conversation offers a clear, grounded reframe.👉 Watch now and start playing the long game. Timestamps:05:51 Rand Stagen personal leadership journey07:47 The advice for young entrepreneurs10:17 Entrepreneurial roots and early influences12:43 Founding the Leadership Academy16:50 Structure of the leadership program22:23 Integral theory explained26:18 Leadership and polarization35:57 Practical advice for leaders41:45 Conscious Capitalism principles45:41 Short term versus long term thinking52:01 Workshop goals and takeaways56:18 Who the workshop is for58:12 Leadership wisdom and closing insight Learn more about MEA at ⁠https://www.meawisdom.com/#LeadershipDevelopment, #ConsciousLeadership, #LongTermThinking, #LeadershipMindset, #PersonalGrowth, #ExecutiveLeadership, #PurposeDrivenLeadership, #InfiniteGame, #MidlifeLeadership, #SelfLeadership, #LeadershipPodcast, #AwarenessAndChoice, #ModernLeadership, #LeadershipWisdom, #ChipConley

Most companies are racing toward AI, efficiency, and scale while quietly losing the one advantage that actually sustains great leadership: wisdom. In this Wisdom Wednesday episode, we reveal why culture, lived experience, and human judgment matter more than ever. Chip draws on decades of leadership experience to explain why many organizations are losing their edge and what they can do to reclaim it. In this episode, you’ll learn:- Why leadership is a practice, not a personality trait- How culture is shaped when leaders aren’t in the room- What companies lose when institutional wisdom disappears- The difference between knowledge workers and wisdom workers in the AI era As technology accelerates, human skills become the real competitive edge.👉 Watch now and discover how wisdom future-proofs leadership and culture. Timestamps:00:13 Leadership as a practice02:29 Culture leaders overlook05:18 Defining real company culture08:57 Institutional wisdom loss13:47 Knowledge workers vs wisdom workers18:30 AI impact on early careers22:22 Humanities and philosophy comeback22:44 Wisdom at Airbnb25:53 Informal mentors and EQ27:57 Leading yourself first28:18 Resources and upcoming workshop30:12 Closing thoughts Learn more about MEA at ⁠https://www.meawisdom.com/#LeadershipWisdom #WisdomAtWork #FutureOfLeadership #AIAndLeadership #CompanyCulture #EmotionalIntelligence #KnowledgeVsWisdom #HumanSkills #MentorshipMatters #InstitutionalWisdom #LeadershipDevelopment #WisdomWednesday #LeadershipCulture #AIImpact #ModernLeadership

Have you ever reached a point in life where what once worked… suddenly doesn’t?In this warm conversation with Chip, Ben Katt, MEA’s faculty in residence and author of The Way Home, offers a hopeful reframe of midlife. Rather than seeing it as a breakdown, Ben invites us to see this season as a meaningful transition, one that asks us to let go of old roles and reconnect with who we truly are. In this episode, you’ll discover:- Why midlife often feels disorienting, even when life looks “successful” on the outside- How releasing familiar identities creates space for deeper purpose and wholeness- Why stillness, reflection, and meditation are essential during times of change- How community and support help us move through transitions with more easy If you’re feeling restless, uncertain, or quietly asking “What’s next?”, this conversation offers clarity, comfort, and a sense of direction.👉 Watch now and explore what this chapter of your life is gently calling you toward.Timestamps:00:35 The Hero’s Journey and The Way Home04:49 Ben’s five-year soul journey07:20 Achievement perfectionism and people pleasing09:44 Meditation and inner balance13:19 Phase 1: Leaving the familiar15:46 Phase 2: Falling into the unknown18:30 Dark night of the ego20:51 Wander in the wild23:56 Support and community29:52 Phase 3: Rising to wholeness33:46 Stillness and begin again38:58 Teaching wisdom without religion44:13 The wisdom well metaphor47:21 Why wisdom matters now50:28 Wisdom bumper sticker Learn more about MEA at ⁠https://www.meawisdom.com/Find Ben Katt at https://benkattofficial.com/ #MidlifeTransition #MidlifeCrisis #MidlifeTransformation #HeroJourney #FindingPurpose #MidlifeWisdom #LifeTransitions #PersonalGrowth #MidlifeAwakening #SecondHalfOfLife #InnerWork #MeaningInMidlife #JosephCampbell #WisdomTraditions #MidlifeChrysalis

What if the wellness advice you followed for years stops working after 50?In this episode, wellness pioneers Jeff Krasno, co-founder of Wanderlust, and Schuyler Grant, founder of Kula Yoga Project, share how their approach to health quietly but radically shifted in midlife, and why many popular wellness habits fall short as we age.With decades spent in yoga, wellness festivals, and lived experience, they share what actually matters now.They share insights on:- Why yoga alone isn’t enough after 50- How muscle and strength shape metabolic and brain health- The importance of diverse movement, not extremes- How simple habits and presence support long-term well-beingThis is a grounded, honest conversation about aging well — without hype or shortcuts.👉 Watch now and rethink what midlife wellness really requires. Timestamps:01:22 Skylar’s yoga studio near Ground Zero05:54 The origins of Wanderlust09:47 Early resistance to the festival idea11:28 Wellness hotels and business travel14:32 Challenges of working with a spouse20:52 What wellness means after 5020:52 Muscle, metabolism, and aging26:30 Yoga versus strength training29:43 Muscle health and brain health31:37 Diversity of movement in midlife34:38 Curiosity, learning, and discomfort37:34 Habit stacking explained40:27 Wellness and politics45:49 Upcoming Baja workshop49:27 Wisdom bumper stickers Learn more about MEA at ⁠https://www.meawisdom.com/ #WellnessAfter50 #MidlifeWellness #HealthyAging #StrengthAfter50 #MuscleAfter50 #AgingWell #Over50Health #MidlifeHealth #LongevityLifestyle #FunctionalFitness #WellnessPodcast #HealthyMidlife #MindBodyHealth #HabitsForHealth #LifeAfter50

Why most New Year’s resolutions fail before February? In this episode of Wisdom Wednesday, we take an honest look at why good intentions fade quickly and share a simple, practical framework for building habits that last. Drawing from real-life experience, we break down how to turn good intentions into daily actions, without relying on motivation alone.In this episode, you’ll learn:- Why most resolutions fail- How habit stacking makes change automatic- The “Four Ps” that make goals stick- Why public accountability matters- How to build habits that last beyond JanuaryIf you’re done repeating the same resolutions every year, this episode will help you do it differently.👉 Watch now and start the year with habits that actually stick.Timestamps:00:44 Morning people and Baja midnight01:39 Why New Year’s resolutions fail02:07 Common resolutions and lack of a plan03:30 Habit stacking explained05:10 Turning resolutions into daily practice06:10 The four Ps framework07:45 Pairing and social accountability08:39 Passion versus accountability09:50 Why fewer goals work better11:03 Learning from past resolutions11:50 Personal resolutions and alcohol13:10 Family time as a long-term priority14:14 Final reflections for 202515:02 Age, milestones, and perspective Learn more about MEA at ⁠https://www.meawisdom.com/#NewYearsResolutions #HabitBuilding #HabitsThatStick #PersonalGrowth #MidlifeWisdom #BehaviorChange #GoalSetting #Accountability #HabitStacking #Mindfulness #SelfImprovement #Longevity #Wellbeing #LifeDesign #WisdomWednesday

Midlife can feel confusing, even when life looks good from the outside. Careers change, relationships shift, and the way we see ourselves starts to evolve, leaving many people feeling stuck in between what was and what’s next.In this episode, Kari Cardinale, Chief Content Officer and partner at Modern Elder Academy, explains why these moments aren’t breakdowns but transitions, and why learning to navigate them is an essential life skill. Through her work on Transitional Intelligence, Kari shares what’s really happening during midlife change and how to move through it with greater clarity and confidence.You’ll learn:• Why most midlife “crises” are actually misunderstood transitions• The three stages of change: endings, the messy middle, and new beginnings• Why the messy middle feels so hard — and why it matters• How rituals, community, and small “glimmers” guide what comes next If you’re feeling stuck or sensing a shift in your life, this episode will help you understand where you are and how to move forward.👉 Navigating Transitions online course from Modern Elder Academy offers a supportive, step-by-step way to work through change with clarity and confidence, starting March 2: https://www.meawisdom.com/navigating-transitions-online/Timestamps:01:20 What is transitional intelligence03:58 The three stages of transition06:02 Voluntary and involuntary change08:02 Why transitions take longer than we expect11:50 The role of ritual in midlife15:54 The messy middle and uncertainty17:53 Glimmers and new beginnings21:44 Growth mindset in midlife24:28 Kari’s personal transition story28:37 The birth of Modern Elder Academy31:36 Love and relationships in midlife34:48 What truly gets better with age37:23 Building community and belonging42:31 Wisdom bumper sticker Learn more about MEA at ⁠https://www.meawisdom.com/#KariCardinale #MidlifeTransitions #MidlifeChange #MessyMiddle #LifeTransitions #PersonalGrowth #MidlifeWisdom #ModernElder #TransitionalIntelligence #EmotionalIntelligence #MidlifePurpose #NewBeginnings #GrowthMindset #MidlifeJourney #InnerWork

He didn’t plan on being successful. He just followed what pulled at him and kept letting go when it stopped working. In this episode, Stacy Peralta, legendary skateboarder, filmmaker behind Dogtown and Z-Boys, and modern elder, shares how a life built on passion, curiosity, and vulnerability led him from skateboarding to filmmaking to painting, without clinging to any single identity. Rather than chasing security or certainty, Stacy reveals why reinvention requires becoming a beginner again and why midlife may be the most powerful time to do it.In this conversation, Stacy explores:- Why holding onto past identities quietly blocks your future- How embracing vulnerability and being a “kook” unlocks growth- The difference between loving something and knowing when to let it go- How intuition, not logic, often guides the most meaningful transitions- Daily practices that keep creativity, curiosity, and vitality alive 👉 Watch the full episode now and discover why letting go might be the most powerful move you can make. Timestamps:00:58 Early life mischief and finding skateboarding03:32 Understanding transitions and success05:57 Realizing it was time to leave skateboarding06:38 Becoming a beginner in filmmaking10:46 Family influence and unconventional paths13:16 Work ethic creativity and self reliance15:19 Learning from surfer elders16:59 Following what you love in midlife18:41 Giving your gift and letting it go20:00 Embracing vulnerability and being a kook24:10 Facing fear of being too old28:00 Flow challenge and skill31:10 MEA workshops experience34:25 Quiet rebellion and midlife dreams37:05 Listening intuition and creating space39:05 Letting go of control41:23 Daily practices for vitality42:46 Harmonizing heart and mind43:07 The power of listening44:51 Closing reflections and gratitude Learn more about MEA at ⁠https://www.meawisdom.com/#StacyPeralta #MidlifeReinvention #ModernElder #PersonalReinvention #MidlifeTransition #GrowthMindset #CreativeLife #LettingGo #SecondAct #PurposeInMidlife #LifeTransitions #DogtownAndZBoys #SkateboardingLegend #BecomingABeginner #Intuition

In this Wisdom Wednesday episode, Chip Conley, entrepreneur, author, and founder of MEA, opens up about the quiet disappointment many high achievers feel after they’ve “made it.”Through stories from building iconic companies, guiding Airbnb’s founders, and navigating midlife reckoning, Chip explores the success treadmill, and why chasing the next win so often leaves us unsatisfied. In this conversation, you’ll learn:- Why success can feel addictive but never fulfilling- The crucial difference between happiness and joy- How a simple gratitude practice can change how life feels day to day- What midlife teaches us about meaning, ego, and impactThoughtful, honest, and deeply human, this episode is an invitation to pause, reflect, and reconnect with what actually matters.👉 Watch now and step off the success treadmill. Timestamps:01:00 Holiday plans and family time01:51 MEA Film Festival vision and growth04:28 Defining success and ambition06:30 Happiness vs. Joy10:03 Making gratitude intentional11:27 Realizing the success treadmill15:21 Ego shift at Airbnb16:32 Getting off the treadmill sooner16:50 Near death experience and perspective18:30 Service as gratitude practice19:40 Facing illness and loss21:33 This too shall pass21:49 Collective gratitude and closing Learn more about MEA at ⁠https://www.meawisdom.com/#SuccessTreadmill #GratitudePractice #MidlifeWisdom #FindingMeaning #HappinessVsJoy #PersonalGrowth #MidlifeTransformation #RedefiningSuccess #LifePurpose #InnerFulfillment #ChipConley #MidlifeCrisis #SelfReflection #LifeLessons #MindfulLiving