Shows
The Midlife ChrysalisWhen Everything Hits at Once: The Art of the Reframe“Stay positive” can feel hollow when cancer returns, someone you love dies, and your marriage is ending.In this Wisdom Wednesday episode, MEA founder and author Chip Conley joins Derek Gehl for a deeply personal conversation about facing all three. Drawing on his upcoming book, The Art of the Reframe, Chip shares how he’s finding a way forward without pretending the pain isn’t real.You’ll discover how to:Feel the grief before trying to find the silver lining.Separate what happened from the story you tell yours...
2026-10-2127 minThe Midlife ChrysalisMEA Film Fest: Come for the Movies, Stay for the ConnectionsWatch a great film, then share dinner with the person who made it. That’s the spirit of the MEA Film Fest, where stories on screen spark conversations and connections in real life.In this Wisdom Wednesday episode, Chip Conley joins Derek Gehl to preview the festival and explore a question at its heart: how can movies help us see midlife, aging, and our own possibilities differently?Get a preview of the films, special guests, and festival experience.Discover stories of reinvention that go beyond the midlife crisis.Explore what yo...
2026-10-1417 minThe Midlife ChrysalisWhen the Life You Built Is No Longer Enough | Caroline MyssMidlife can feel like the life you built suddenly stops fitting. Caroline Myss believes there’s a deeper reason: this is when the soul begins asking something different of you.In this powerful conversation, bestselling author and spiritual teacher Caroline Myss joins Chip Conley to explore the deeper meaning of midlife, purpose, identity, and surrender.Caroline shares:Why a crisis of purpose may actually be a crisis of the soulHow we move from job to career to callingWhy we lose our appetite for the life we’ve builtHow sacr...
2026-10-0954 minThe Midlife ChrysalisWhat If the Life You Built Isn’t the Life You Want?You’ve built a life that looks successful. Yet the things you worked so hard for may no longer be what you want next.In this Wisdom Wednesday episode, MEA founder Chip Conley joins Derek Gehl to explore finding purpose when familiar roles no longer feel fulfilling. From a corporate lawyer investing in her community to former business owners pursuing screenwriting, Chip shares how people are discovering possibilities they had quietly put aside.You’ll hear:How to recognize someone else’s success script and begin defining success for yo...
2026-10-0723 minThe Midlife ChrysalisHe Died 11 Years Ago. Their Relationship Never Ended. | Lucy KalanithiEleven years after losing her husband, the pain has changed. The love hasn’t.Dr. Lucy Kalanithi, physician and widow of Paul Kalanithi, author of When Breath Becomes Air, joins Chip Conley for a deeply personal conversation about grief, caregiving, uncertainty, and building a meaningful life after profound loss.Drawing on her experience as a wife, mother, caregiver, and doctor, Lucy shares what more than a decade of living with grief has taught her:Why death doesn’t necessarily end our relationship with someone we loveHow grief changes over...
2026-10-0544 minThe Midlife ChrysalisThe Hardest Leadership Lesson: Let Someone Else Be the HeroBeing the person who saves the day feels good. But letting someone else do it can make you a better leader.MEA founder Chip Conley joins Derek Gehl to talk about one of the hardest changes in his career: moving from hero to coach. Chip shares how he is learning to step back, trust his team, and make room for others to lead.Why having all the answers can hold your team backHow asking questions helps others grow into leadersWhy purpose matters as an organization gets biggerHow to build something...
2026-09-3027 minThe Midlife ChrysalisWhat Changes When You Finally Let Go of Control? | Thomas DeLongSuccess can look impressive on a résumé and still leave you wondering who you really are.At 76, Harvard Business School professor and former Morgan Stanley executive Thomas DeLong is rethinking some of the biggest lessons he has learned about leadership, courage, relationships, and success. In this conversation with Chip Conley, he reflects on:Why letting go of control can deepen relationshipsHow to move from image management to essenceWhy vulnerability is a powerful form of courageHow inherited success scripts can define the path we followWhy later life is ab...
2026-09-2835 minThe Midlife ChrysalisBe Useful, Not Youthful: The Secret to Aging WellAt some point in midlife, achievement stops being enough. The titles matter less, the phone may stop ringing, and the question becomes: where does your value come from now?In this episode of Wisdom Wednesday, MEA founder Chip Conley joins Derek Gehl to explore the shift from achievement and admiration toward generativity, usefulness, and helping others grow.Key insights include:Why feeling invisible doesn’t mean becoming irrelevantHow to move from “sage on the stage” to “guide on the side”Why being useful matters more than staying youthfulHow becoming “...
2026-09-2324 minThe Midlife ChrysalisWhy Birthdays Matter More as We Get OlderWhy do we celebrate birthdays as kids, then slowly stop celebrating ourselves as we get older?In this episode of The Midlife Chrysalis, Chip Conley joins Derek Gehl for a conversation about birthdays, aging, and why life’s milestones deserve more attention, not less.After decades of marking his own milestone birthdays in memorable ways, Chip shares why celebration has become even more meaningful as he’s grown older and faced his own mortality.Key insights from the episode:Birthdays are more than a nu...
2026-09-1622 minThe Midlife ChrysalisSurfing at 87, Writing at 91: James Flaherty’s Rules for LifeAt 91, James Flaherty isn’t slowing down. He’s still writing, creating, learning, and planning what comes next.A former advertising executive, entrepreneur, innkeeper, and author who wrote five books in his 80s, James joins Chip Conley to share what nine decades of living have taught him about aging well and staying fully engaged with life.In this episode, James shares:Stay useful, not youthful. Growing older brings experience and wisdom that can be put to work for others.Always have a reason to wake up. Purpose, goals, and...
2026-09-1448 minThe Midlife ChrysalisFrom Role to Soul: Who Are You Without What You Do? | Connie ZweigAging isn’t just about getting older. It’s about discovering who you are when the roles that once defined you begin to fall away.In this episode, Chip Conley sits down with Connie Zweig, author of The Inner Work of Age, to explore the deeper psychological and spiritual work of midlife and beyond.Connie shares what it takes to move from simply growing old to becoming an elder, including:Moving from role to soul: Why identity built around achievement and productivity may need to loosen as we age...
2026-09-1149 minThe Midlife ChrysalisYou Can’t Rush Grief: Learning to Feel What We’ve LostSome losses hit harder than we ever expect, and grief doesn’t follow our timeline.In this deeply personal episode of Midlife Chrysalis, Chip Conley opens up about the unexpected death of his beloved dog Jamie and what the experience has taught him about grief, love, and loss.Key insights from the episode:Grief comes in waves. It can surface as sadness, anger, exhaustion, or simply the need for space.You can’t rush grief. Searching for meaning too quickly can keep us from actually feeling what we’ve los...
2026-09-0922 minThe Midlife ChrysalisFrom Doing to Being: The Power of Presence | Teddi DeanSometimes the most powerful thing we can do is stop doing and simply be present.In this episode, Chip Conley talks with Teddi Dean, former Bones Brigade skateboarder turned filmmaker, mindfulness teacher, and Head of Mind & Body at MEA. Teddy shares his journey through sobriety, yoga, meditation, and decades of exploring what it means to live with greater awareness.You’ll discover:Why stillness can be transformative and help us reconnect with ourselves.How 10 to 20 minutes of daily mindfulness can change how we re...
2026-09-0449 minThe Midlife ChrysalisCuriosity Is the Secret to a Richer LifeHappiness and purpose may not be enough for a truly rich life.In this episode of The Midlife Chrysalis, Chip Conley joins Derek Gehl to explore psychological richness and why curiosity, new experiences, challenge, and spontaneity become especially valuable as we age.You’ll discover:Why psychological richness matters as we get older and how curiosity keeps us engaged with life.The question that can reshape your next decade: What will you regret not learning, doing, or investing in 10 years from now?Why becoming a beginner again matters, fr...
2026-09-0224 minThe Midlife ChrysalisWe’re Living Longer. Why Isn’t Society Ready? | David SinclairThe longevity revolution isn’t coming. We’re already living it, and we’re not ready.In this episode, David Sinclair of the International Longevity Centre joins Chip Conley to explore what longer lives mean for all of us and why society needs to catch up with a future that’s already here.In this conversation:Why the real longevity challenge isn’t living to 100, but adapting to longer lives todayWhy prevention needs to play a much bigger role in how we approach health and agingHow longer lives are changi...
2026-08-3145 minThe Midlife ChrysalisCould Living Together Be the Secret to Aging Better?Growing older is changing. Maybe the way we live should change with it.In this episode of Wisdom Wednesday, Chip Conley joins Derek Gehl to explore a new approach to later life: shared homes that combine independence, connection, and community.Drawing on MEA’s growing Golden Girls experiment, Chip shares:Why traditional senior living and aging in place don’t work for everyoneWhat MEA has learned from its first shared homes and Golden Girls retreatsWhy privacy, flexibility, and compromise are essential to making shared living workHow shared homes can...
2026-08-2623 minThe Midlife ChrysalisYou Got Everything You Wanted. Now What? | Edward SullivanWhat happens when you achieve the success you've worked for... and it still doesn't feel like enough?In this episode of The Midlife Chrysalis, Chip Conley sits down with executive coach and Velocity Coaching founder Edward Sullivan to explore one of the most overlooked challenges of midlife: figuring out what comes after success.Drawing on years of coaching founders, CEOs, and high achievers, Edward shares why so many people feel restless after reaching major goals, how AI is reshaping work and leadership, and what it really takes to build...
2026-08-2450 minThe Midlife ChrysalisFollow the Energy, Not the Career Script | Arun GuptaYour job title tells people what you do. The problem you care about tells them who you are.Arun Gupta, CEO of NobleReach and co-author of The Mission Generation, joins Chip Conley for a thoughtful conversation about finding purpose, staying curious, and creating a meaningful career at every stage of life.Some of the ideas they explore:Why following your energy can lead you somewhere a career plan never couldHow becoming a beginner again can bring fresh energy to midlifeWhy learning, earning, and giving back can happen throughout...
2026-08-2149 minThe Midlife ChrysalisHow to Discover the Gift That’s Uniquely Yours?What if the thing that makes you different has been there all along, you just haven’t named it yet?In this Wisdom Wednesday, Chip Conley and Derek Gehl explore how to “excavate your essence” and uncover the unique gift that can guide your work, choices, and life.You’ll discover:How Airbnb uncovered “Belong Anywhere” by looking beyond what the company does to why it mattersA simple five-question exercise for getting beneath the obvious answersHow Chip discovered his gift as a “social alchemist” and used it to better understan...
2026-08-1915 minThe Midlife ChrysalisHow to Talk to People You Profoundly Disagree With | Shamil IdrissHow do you find common ground with someone you profoundly disagree with?At a time when political, religious, and cultural divisions seem deeper than ever, peacebuilder Shamil Idriss, CEO of Search for Common Ground, shares what decades of bringing people together have taught him about trust, conflict, and human connection.In this conversation with Chip Conley, Shamil explores:Why being heard and respected matters more than being agreed withHow building trust before a crisis can bridge even deep dividesWhy curiosity is more powerful than judgmentHow taking just one...
2026-08-1745 minThe Midlife ChrysalisWhy Retirement Is the Wrong Goal | Ken DychtwaldMidlife isn't the beginning of the end. For more than 50 years, Dr. Ken Dychtwald, psychologist, bestselling author, and founder of Age Wave, has studied what it really means to grow older.In this conversation, he explains why midlife isn't the beginning of the end, but the start of one of life's most meaningful transformations.In this episode, you'll discover:Why midlife is a time of growth, not declineThe powerful idea of "middle essence" and how it changes the way we think about agingWhy retirement may be one of...
2026-08-1447 minThe Midlife ChrysalisWhy Midlife Feels Stuck (And How to Break Free)Don't wait until it's too late to tell someone what they mean to you.In this inspiring Wisdom Wednesday episode, Chip Conley joins host Derek Gehl to share a powerful idea that could change the way we celebrate the people we love: the social eulogy. Instead of waiting until a funeral, why not tell people the impact they've had on your life while they're still here to hear it?In this episode, you'll learn:Why we struggle to express appreciation when it matters most.The difference between a...
2026-08-1223 minThe Midlife ChrysalisHow Psilocybin Can Change Your Life After 40 | Neil MarkeyCould one guided psychedelic experience transform the way you think, feel, and live?In this episode of The Midlife Chrysalis, Chip Conley speaks with Neil Markey, CEO of Beckley Retreats, former Army Ranger captain, McKinsey consultant, and Harvard public health student, about the growing role of psilocybin in personal transformation and mental well-being.Together, they explore:Why midlife may be the ideal time for a psychedelic experience.What really happens during a professionally guided psilocybin retreat.Why preparation and integration are just as important as the experience itself...
2026-08-1055 minThe Midlife ChrysalisYour Brain Is Lying to You About Happiness | Dr. Laurie SantosWe've been chasing happiness the wrong way. Dr. Laurie Santos explains what actually works.Join Chip Conley and Dr. Laurie Santos, Yale's renowned happiness professor and creator of the university's most popular course, for a thought-provoking conversation on the science of happiness, the opportunities of midlife, and the habits that lead to a more fulfilling life.In this episode, you'll discover:Why your brain often pushes you toward the wrong definition of successThe habits that matter more than money, achievement, or statusHow your mindset can shape your happiness...
2026-08-0745 minThe Midlife ChrysalisWhy High Achievers Still Feel Like ImpostersDo you ever feel like you're not good enough, even when you're succeeding?You're not alone. In this Wisdom Wednesday, Chip Conley explores why imposter syndrome follows so many high achievers and, more importantly, how to break free from it.In this conversation, you'll discover:Why imposter syndrome doesn't disappear with successHow to replace fear with curiosity and become an "explorer" instead of an imposterWhy vulnerability often earns more respect than pretending to be perfectA simple mindset shift that makes taking risks feel much less overwhelmingHow embracing beginner...
2026-08-0525 minThe Midlife ChrysalisWhy Your 70s Can Be Your Most Meaningful Years | Dr. Philip PizzoWhat if your most meaningful chapter begins after 70?Most people think aging is about slowing down. Dr. Philip Pizzo believes it's about discovering new purpose.In this inspiring conversation, Chip Conley sits down with Dr. Philip Pizzo, former Dean of Stanford Medicine, founder of the Stanford Distinguished Careers Institute (DCI), physician, educator, and now a spiritual care provider, to explore how we can navigate life's biggest transitions with meaning.In this episode, you'll discover:Why purpose, community, and wellness are the foundation of...
2026-07-3149 minThe Midlife ChrysalisDon't Save It for the Funeral: The Power of a Social EulogyDon't wait until it's too late to tell someone what they mean to you.In this inspiring Wisdom Wednesday episode, Chip Conley joins host Derek Gehl to share a powerful idea that could change the way we celebrate the people we love: the social eulogy. Instead of waiting until a funeral, why not tell people the impact they've had on your life while they're still here to hear it?In this episode, you'll learn:Why we struggle to express appreciation when it matters most.The difference between a...
2026-07-2919 minThe Midlife ChrysalisThe Hero’s Journey: Crossing the Threshold from Stagnation to Generativity | Pat WhittyAt an age when many people are slowing down, Pat Whitty walked 200 miles on Spain's Camino de Santiago — alone. But what started as a physical challenge became a profound journey of self-discovery, purpose, and spiritual renewal.In this inspiring conversation, Chip Conley sits down with Pat to explore what happened when he stepped away from the noise of everyday life and spent 16 days walking with nothing but his thoughts.In this episode, you'll discover:Why it's never too late to pursue a dream you've been putting off for ye...
2026-07-2746 minThe Midlife ChrysalisThe Power of Play in Reinventing Your Life | Kristine Michie & JD SchrammPlay isn't just for kids. It's one of the most powerful tools for navigating change, finding purpose, and becoming more fully yourself.In this episode of Midlife Chrysalis, Chip Conley sits down with Kristine Michie founder of the Playful Podcast, and JD Schramm, communication expert and former Stanford professor, to explore how play, storytelling, and authenticity can transform the way we approach midlife.What you'll discover:Why losing a job can become the beginning of your next chapter.How the need to impress others quietly shapes our identity...
2026-07-2445 minThe Midlife ChrysalisCan AI Ever Be Wise? Knowledge vs. Human ExperienceCan AI really replace human wisdom? Or are we undervaluing the one thing machines will never have?In this Wisdom Wednesday, Chip Conley and Derek Gehl explore a powerful idea inspired by the Spanish language: there are two different ways of "knowing." One is knowledge anyone, including AI, can access. The other comes only through lived experience.In this conversation, you'll discover:Why AI can know facts but will never have real wisdom.The difference between knowing something and experiencing it.Why stories are more powerful than information...
2026-07-2221 minThe Midlife ChrysalisThe Science Behind a Better Midlife| Dr. Margie E. LachmanMidlife is far more hopeful and full of possibility than most of us have been led to believe.In this episode of The Midlife Chrysalis, Chip Conley talks with Dr. Margie E. Lachman, one of the world's leading experts on lifespan psychology, director of the landmark MIDUS study, and author of Prime Time. Drawing on decades of research, she shares why midlife is one of the most important stages of life and how the choices we make today shape our future health, happiness, and sense of purpose.In this...
2026-07-2045 minThe Midlife ChrysalisHow Time Away Can Change Your Future | DJ DiDonnaBurnout, career uncertainty, and midlife stuckness have become increasingly common, but stepping away may be the key to moving forward.In this episode, Chip Conley sits down with DJ DiDonna, Harvard Business School senior lecturer, entrepreneur, and author of Big Time Off. After reaching burnout while running his dream company, DJ took a four-month sabbatical that transformed his perspective on work, success, and life.In this conversation, DJ shares:Why burnout is often a sign that something needs to changeHow sabbaticals create space for clarity, growth, and reinventionThe...
2026-07-1349 minThe Midlife ChrysalisThe Soul of Money: Why Life Gets Better After 50 | Lynne Twist & Sara VetterCan your greatest purpose begin after 50?In this powerful conversation, Chip Conley sits down with Lynne Twist, bestselling author of The Soul of Money, and her longtime collaborator Sara Vetter to explore purpose, money, mentorship, and the surprising opportunities that come with midlife.In this episode, you'll learn:Why midlife can be the start of your most meaningful chapter.How a life-changing trip to the Amazon transformed their paths.The mindset shift that can completely change your relationship with money.Why great partnerships are built on trust, honesty...
2026-07-1057 minThe Midlife ChrysalisHow Wise People Handle UncertaintyUncertainty is everywhere, from economic shifts and AI disruption to health challenges and major life transitions. The question isn't how to eliminate uncertainty, but how to navigate it with confidence.In this Wisdom Wednesday episode, Chip Conley and Derek Gehl explore practical ways to stay grounded when life feels unpredictable. Drawing from his experiences as an entrepreneur and his ongoing cancer journey, Chip shares the tools that have helped him face uncertainty with greater resilience, clarity, and purpose.In this episode, you'll learn:Why uncertainty is a normal...
2026-07-0823 minThe Midlife ChrysalisThe Skills That Will Matter Most in the AI Era | Chris Shipley & Scott Barry KaufmanAI is changing the way we work, but the skills that matter most are still deeply human.In this episode of The Midlife Chrysalis, Chip Conley is joined by Chris Shipley, technology visionary and leadership expert, and Scott Barry Kaufman, psychologist and bestselling author, for a thoughtful conversation about leadership, purpose, and human potential in the age of AI.Together, they explore why the future belongs to leaders who combine technology with wisdom, curiosity, and genuine human connection.In this episode, you'll discover:...
2026-07-0645 minThe Midlife ChrysalisThe Biggest Myth We Believe About Aging | Dr. Michael GurvenMost of us have been taught that humans used to die young, aging means decline, and longevity is something only modern science can unlock. Anthropologist Dr. Michael Gurven offers a very different perspective.In this episode of Midlife Chrysalis, Chip Conley sits down with Dr. Gurven, author of Seven Decades, to explore what indigenous cultures can teach us about aging, health, purpose, and living well.Together, they discuss:Why humans often lived much longer than we assumeWhat traditional societies reveal about healthy aging and chronic diseaseWhy elders earned...
2026-07-0349 minThe Midlife ChrysalisStop Trying to Fit In: The Hidden Gift of AgingWhat if one of the greatest gifts of aging is finally caring less about fitting in?In this Wisdom Wednesday conversation, Chip Conley and Derek Gehl explore why growing older isn't just about gaining wisdom, but about gaining the freedom to become more fully yourself.Chip shares why authenticity becomes more important than achievement, how we shift from building a resume to building a legacy, and why embracing your quirks may be one of the healthiest forms of personal growth.In this episode, you'll...
2026-07-0122 minThe Midlife ChrysalisCan Your Mind Change How You Age? | Ellen LangerAging may have less to do with your body than you think.In this fascinating conversation, Chip Conley talks with Harvard psychologist Ellen Langer, whose groundbreaking research has spent decades challenging what we think we know about aging, health, mindfulness, and human potential.Drawing on stories from her life and her famous Counterclockwise study, Ellen explains why many of the limits we accept as part of growing older may be more flexible than we realize.In this episode, you'll discover:Why mindfulness begins...
2026-06-2949 minThe Midlife ChrysalisWhy We Spend Years Chasing Things We Don't Really Want | Alain de BottonYou followed the rules, built a successful career, and checked the boxes you thought would make you happy. So why does something still feel missing?In this powerful conversation, bestselling author, philosopher, psychotherapist, and founder of The School of Life, Alain de Botton joins Chip Conley to explore what midlife teaches us about happiness, relationships, purpose, and becoming more fully ourselves.In this episode, you'll learn:Why status, success, and achievement often fail to deliver lasting fulfillmentHow heartbreak, loneliness, and setbacks can become sources of wisdomWhy friendship becomes...
2026-06-2647 minThe Midlife ChrysalisScience Says Aging Can Make You Happier | Laura CarstensenThe science of aging reveals a surprising truth: many people become happier as they get older.In this episode of Midlife Chrysalis, Chip Conley sits down with Laura Carstensen, psychologist, longevity expert, and founder of the Stanford Center on Longevity, to explore the science of aging, happiness, and living longer.Key insights from this conversation:Why older adults are often happier than younger peopleHow aging changes the brain and increases our focus on positive experiencesWhy the search for immortality may actually make life less meaningfulHow longer lifespans are...
2026-06-2248 minThe Midlife ChrysalisWhy So Many of Us Feel Like We Don't Belong | Pádraig Ó TuamaWhat does it mean to belong, to yourself, to others, and to a life that's constantly changing?In this powerful conversation, Chip Conley sits down with Irish poet, theologian, and conflict mediator Padraig O Tuama to explore belonging, grief, identity, faith, and the wisdom that comes with midlife.You'll learn:Why belonging isn't always what we think it isHow poetry helps us navigate loss and uncertaintyPadraig's journey through religion, sexuality, and reparative therapyWhat turning 40 taught him about mortality and meaningWhy love may be life's most important practice
2026-06-1952 minThe Midlife ChrysalisWhen Success Isn't Enough: Finding Purpose in MidlifeMany successful people reach midlife with a surprising question: What's next?In this episode of Wisdom Wednesday, Chip Conley shares what he's learning from leading the Purpose Fellowship, a year-long program helping people redefine purpose beyond career, achievement, and old identities.Chip explores why so many high achievers struggle to find meaning after success, how hidden patterns influence our choices, and why purpose is often much broader than we realize.In this conversation, you'll learn:Why purpose is not just one thing for...
2026-06-1727 minThe Midlife ChrysalisWhat Comes After You've Achieved Everything? | Bill GeorgeHe had the career, the success, and the recognition. So why was he miserable?In this episode, Chip Conley sits down with leadership expert, bestselling author, and former Medtronic CEO Bill George to explore why success without purpose can leave even the most accomplished people feeling unfulfilled.Drawing from personal loss, career setbacks, and decades of leadership experience, Bill shares the lessons that helped him discover his True North and build a life centered on meaning rather than achievement.You'll learn:Why success...
2026-06-1548 minThe Midlife ChrysalisWhy Time Speeds Up as You Get Older (And How to Slow It Down)Why does time seem to move faster every year?One moment you're raising young children. The next, they're leaving home. So where does the time go?In this Wisdom Wednesday, Chip Conley and Derek Gehl explore one of life's biggest mysteries: why time feels faster as we age and what we can do about it.You'll discover:Why being a beginner makes life feel longerHow flow states help us become fully presentThe surprising link between mortality and happinessWhy purpose, mindset, and relationships matter...
2026-06-1024 minThe Midlife ChrysalisThe Truth About Becoming Miserably Successful | Debjani BiswasWhat happens when you do everything “right” in life… and still end up unhappy?In this powerful conversation, I’m joined by Debjani Biswas, leadership coach, bestselling author, and TEDx speaker, to talk about burnout, reinvention, identity, and what it really means to live authentically. She shares her journey from turning down Harvard twice and breaking barriers as the only woman in her IIT engineering class to experiencing a complete midlife unraveling that changed everything.Together with Chip Conley, she explores:Why so many successful people feel empty insideHo...
2026-06-0550 minThe Midlife ChrysalisThe Millennial Midlife Crisis Won't Look Like You ThinkAre Millennials heading for a midlife crisis or redefining midlife altogether?In this Wisdom Wednesday episode, Chip Conley joins Derek Gehl to explore how millennials are entering midlife differently than previous generations. After growing up through economic uncertainty, social change, and shifting life expectations, many millennials may be approaching midlife with a completely different mindset than their parents.They discuss:Why millennials may never experience a traditional midlife crisisHow the U-curve of happiness is changing for younger generationsWhy millennials are shifting from freedom-seeking to stability-seekingHow longer lifespans are...
2026-06-0322 minThe Midlife ChrysalisThe Decade Game That Can Transform Your Future | Carolyn Buck LuceMany people reach midlife feeling successful on paper but disconnected from themselves.In this conversation, Chip Conley talks with Carolyn Buck Luce about what it actually looks like to rebuild your life in your 40s, 50s, 60s, and beyond. Carolyn opens up about leaving Wall Street, going through a very public personal crisis, redefining ambition, and creating the “Decade Game”, a simple but powerful way to think about who you want to become over the next 10 years.They talk about:Why purpose often starts showing up earlier than we r...
2026-06-0141 minThe Midlife ChrysalisHow to Turn Anxiety Into Wisdom, Clarity, and ResilienceAnxiety, burnout, and emotional overwhelm make a lot more sense once people understand what’s actually driving them.In this episode, Chip Conley, founder of MEA, former Airbnb executive, and bestselling author of Emotional Equations, talks with Derek Gehl about the hidden patterns behind anxiety, fear, purpose, and emotional resilience.Chip shares powerful insights on:Why anxiety comes from uncertainty and powerlessnessThe difference between fear and anxietyHow painful experiences become future wisdomWhy emotions begin in the bodyThe difference between purpose and emotional escapeChip al...
2026-05-2722 minThe Midlife ChrysalisWhy Deep Listening is the Key to Transformation | Gail LarsenThe parts of ourselves we silence are often the very things that make us come alive.In this heartfelt episode of Midlife Chrysalis, I sit down with Gail Larsen, transformational speaking teacher, author, and longtime MEA faculty member, for a soulful conversation about authenticity, creativity, aging, and finding your voice.From growing up in a restrictive religious environment to helping thousands of people discover their “original medicine,” Gail shares the wisdom she’s gathered through decades of transformation and deep listening.Together, we explore:Why...
2026-05-2548 minThe Midlife ChrysalisWhy So Many Successful People Struggle With RetirementWhy So Many Successful People Struggle With Retirement What Comes After Ambition but Before Retirement?The Hidden Midlife Crisis Between Success and Retirement What happens when you stop chasing success… but you’re not ready to retire? In this episode of Midlife Chrysalis, Chip Conley and Derek Gehl explore a stage of life many people experience but rarely talk about: feeling caught between ambition and retirement. Chip shares personal stories about aging parents, purpose, and how his own view of success changed over time. He explains why midlife...
2026-05-2021 minThe Midlife ChrysalisFeeling Stuck at 50: How to Find Your Magic and Start Again | Matt RossThe moment everything starts falling apart might be the moment your life finally comes together.In this episode, Chip Conley sits down with entrepreneur and author of Grow or Fold, Matt Ross, to explore a powerful story of midlife reinvention. From a high-pressure career in radio to building purpose-driven businesses, Matt shares how personal crisis, burnout, and uncertainty became the catalyst for real change.Here’s what you’ll take away:Why feeling “stuck” at 50 is often the start of something betterThe simple mindset shift that turns breakdown into bre...
2026-05-1153 minThe Midlife ChrysalisWhat Horses, Death, and Nature Taught Me About Being Human | Kelly WendorfWhat if the life you built… no longer feels like yours?In this powerful episode, Kelly Wendorf joins Chip Conley for a raw conversation about loss, identity, and the moment everything shifts. From caring for a dying parent to rediscovering yourself through nature, this episode goes straight to the heart of what it means to truly live.Here’s what you’ll take away:Why success can still leave you feeling emptyHow facing death reshapes how you see lifeWhat “rewilding” really means and why it mattersHow nature (and horses) re...
2026-05-0850 minThe Midlife ChrysalisAI vs Humans: The One Skill AI Still Can’t ReplaceAI is changing work faster than anyone expected… but most people are focusing on the wrong thing.In this episode, Chip Conley and Derek Gehl break down what AI actually means for your career, especially if you're in midlife and wondering where you fit in.Here’s what matters:AI is replacing routine work first, not higher-level thinkingWisdom now matters more than knowledge in an AI-driven worldOver-relying on AI can weaken your own skillsCuriosity and adaptability are your biggest advantagesThis isn’t about fear...
2026-05-0616 minThe Midlife ChrysalisWhy Success Stops Making You Happy After 40You checked all the boxes… so why does something still feel off? In this episode, Chip Conley and Derek Gehl explore what happens when success stops feeling like success, and why so many people hit this wall in midlife. And what you can do when you get there.Here’s what you’ll learn:The 3 questions that reveal your true directionWhy achievement alone doesn’t lead to fulfillmentThe hidden trap of defining success through workWhy relationships matter more than you thinkHow to start redefining success in a way that act...
2026-04-2925 minThe Midlife ChrysalisTake a Month Off and See Who You BecomeWhat if you gave yourself 30 days… with nothing planned?In this episode, Chip Conley shares a deeply personal idea he’s exploring: stepping away from a busy life for a full month: no schedule, no expectations, just space to listen, reflect, and reset.It’s not about escaping life. It’s about returning to it with more clarity and intention.Few ideas from the episode that might stay with you:What it actually means to “disappear” for 30 daysWhy hearing your own eulogy might hit harder t...
2026-04-2223 minThe Midlife ChrysalisHow to Heal Trauma in Your Body and Mind | Rebecca & JaimieIn this powerful episode of the Midlife Chrysalis, Chip Conley sits down with two women who’ve pushed their limits, physically, emotionally, and psychologically, and came out transformed. Meet Rebecca Rusch, a world-class endurance athlete who biked the Ho Chi Minh Trail to reconnect with her late father, and Jaimie Lusk, a former Marine turned psychologist helping veterans heal from deep psychological wounds. Together, they reveal what happens when life forces you to face what you’ve been avoiding.Here’s what you’ll discover:Why midlife isn’t a crisis...
2026-04-2044 minThe Midlife ChrysalisStop Living on Autopilot. Start Living for Real | Bonnie WanMost 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 li...
2026-04-1752 minThe Midlife ChrysalisKnowledge Won’t Save You. Curiosity WillYou 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 engagedIt’s a simple...
2026-04-1527 minThe Midlife ChrysalisStuck 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
2026-04-0819 minThe Midlife ChrysalisWhy 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 disconne...
2026-04-0119 minThe Midlife ChrysalisMen vs Women in Midlife: The Struggles No One Warns You AboutMost people imagine a midlife crisis as sports cars, bad decisions, and dramatic life changes. But what if midlife is actually something much deeper and more meaningful?In this episode of Midlife Chrysalis, Chip Conley explores what really happens during midlife and why men and women often experience it differently. Chip shares insights from years of research and thousands of midlife transitions, revealing the real challenges people face in their 40s, 50s, and beyond.In this conversation, you’ll learn:Why midlife is often a feeling of being st...
2026-03-2525 minThe Midlife ChrysalisWhy Love Requires Skills Most People Never Learn | Terry RealWhy do so many relationships lose intimacy over time, even when love is still there?In this episode of Midlife Chrysalis, Chip Conley talks with renowned couples therapist Terry Real, creator of Relational Life Therapy and bestselling author of Fierce Intimacy and The New Rules of Marriage. For decades, Terry has helped couples understand why connection fades—and how to rebuild it.In this conversation, he explains:Why love requires skills most people were never taughtHow childhood patterns quietly shape adult relationshipsWhy traditional masculinity often blocks emotional intimacyHow co...
2026-03-2347 minThe Midlife ChrysalisPete Holmes on Psychedelics, God & Finding Meaning in MidlifeThe moment that breaks your life can also be the moment that transforms it. In this episode of Midlife Chrysalis, Chip Conley sits down with comedian and writer Pete Holmes for a deep and surprisingly funny conversation about heartbreak, spirituality, and the search for meaning. Pete shares how a painful divorce in his twenties pushed him to fully commit to comedy and set him on a journey into consciousness, psychedelics, fatherhood, and what it really means to live a good life.In this episode, Pete reveals:How his divorce...
2026-03-201h 01The Midlife ChrysalisMidlife Pit Stop: Refuel Before the Next ChapterWhat if the most powerful move you could make at midlife… is to pause?In this episode of Wisdom Wednesday, Derek sits down with Chip Conley to explore the rise of the midlife sabbatical and why more people over 50 are choosing a reset instead of racing toward retirement. Chip challenges the old “learn, earn, retire” model and introduces a new idea: the midlife pit stop — a courageous break to refuel before the next chapter.In this conversation, you’ll learn:Why a sabbatical isn’t a vacation...
2026-03-1826 minThe Midlife ChrysalisDesigning the Second Half of Life: Meaning, Curiosity, and Becoming | Bill Burnett & Dave EvansMost of us try to solve midlife. What if that’s exactly the wrong approach?In this episode, Chip Conley sits down with Bill Burnett and Dave Evans, the minds behind Designing Your Life, to rethink one of the most misunderstood seasons of adulthood. Drawing from design thinking, human curiosity, and decades of real-world experimentation, they offer a refreshing alternative to the pressure of “figuring it all out.”Instead of chasing the right answer, Bill and Dave invite us to prototype our way forward gently, curiously, and without fear of get...
2026-03-1657 minThe Midlife ChrysalisWhy You Keep Repeating the Same Conflict Patterns | Diana ChapmanReal growth rarely happens when life feels comfortable. It begins when we slow down, question our patterns, and face the deeper truths about how we live and lead.In this episode of Midlife Chrysalis, Chip Conley talks with Diana Chapman, leadership coach and co-author of The 15 Commitments of Conscious Leadership. Drawing from decades of coaching founders and CEOs, Diana shares practical wisdom on how awareness can transform relationships, leadership, and personal growth.In this conversation, she explores:How the Drama Triangle fuels conflict and how to step out...
2026-03-1356 minThe Midlife ChrysalisFrom Ego to Soul: Rewriting the Second Half of LifeThe drive that made you successful may not be meant to lead you forever.In this Wisdom Wednesday episode of The Midlife Chrysalis, Chip Conley and Derek Gehl explore the shift from ego to soul, the defining transition of the second half of life. Drawing from his personal journey, his role as a “modern elder” at Airbnb, and insights from Richard Rohr and Connie Zweig, Chip reflects on what happens when achievement stops being enough.In this conversation, you’ll learn:Why ego builds the first half of life b...
2026-03-1124 minThe Midlife ChrysalisLetting Go in Midlife: What Has Run Its Course?Midlife isn’t about adding more. It’s about letting go.In this Wisdom Wednesday episode of The Midlife Chrysalis, Chip Conley joins Derek Gehl to explore The Great Midlife Edit, the courage to release what has quietly run its course.Drawing from his near-death experience and the sale of his company, Chip shares what it really means to “empty your cup” and create space for what’s next.In this conversation, you’ll learn:Why midlife shifts us from accumulation to editingHow to recognize...
2026-03-0422 minThe Midlife ChrysalisWhat a Cancer Diagnosis Teaches You About How to LiveWhat happens when time stops feeling endless and starts feeling real?In this episode of Wisdom Wednesday, Chip Conley shares how living with cancer reshaped his relationship with time, purpose, and urgency in midlife. Joined by Derek Gehl, Chip reflects on cancer scans, mortality, and why remembering that life is finite can actually deepen meaning, not fear. Together they explore:Why memento mori can bring clarity, not darknessHow midlife urgency is about intention, not panicWhat legacy really means beyond achievement...
2026-02-2528 minThe Midlife ChrysalisFrom Ambition to “I’m Enough” | Brian CheskyIn this candid and heartfelt conversation, Airbnb co-founder and CEO Brian Chesky joins Chip Conley to explore the hidden side of success. From imposter syndrome to the emotional aftermath of the IPO, Brian shares what midlife has taught him about ambition, belonging, and finally realizing he is enough. In this episode, you’ll hear:• Why success didn’t fix his loneliness• How leadership evolved from control to connection• The wake-up call that followed Airbnb’s $100B milestone• Why midlife is a chance to redefine what truly matters This is a conversation about growth, vulnerability, and choosing relationships over relentless achievement.If...
2026-02-231h 08The Midlife ChrysalisYour Brain on Art: Why Midlife Needs Creativity More Than Ever | Susan Magsamen & Ivy RossMidlife isn’t a crisis. It’s an invitation to come alive again.In this episode of Midlife Chrysalis, Chip Conley is joined by Susan Magsamen, a neuroscientist at Johns Hopkins, and Ivy Ross, Chief Design Officer at Google, for a warm, eye-opening conversation about why creativity is essential to being human, especially in midlife.Drawing from their book Your Brain on Art, they share how art, play, and sensory experiences quietly support brain health, emotional balance, and a deeper sense of meaning in a world obsessed with productivity and...
2026-02-2051 minThe Midlife ChrysalisWhy Midlife Friendships Stop Working & How to Fix ThemEver notice how some friendships don’t end, they just stop deepening?You still care about each other, but the conversations feel thinner than they used to. In midlife, that quiet shift is more common than we admit.In this Wisdom Wednesday episode, Chip Conley, founder of MEA, joins Derek Gehl for a warm, honest conversation about friendship in the second half of life: why it changes, why it matters more than ever, and how it can grow again.What you’ll take away:Friendship is a practice, not...
2026-02-1819 minThe Midlife ChrysalisWhat Great Mentors Do Differently in MidlifeMost of us grow up thinking mentorship means having the answers. In midlife, we learn it’s really about asking better questions.In this Wisdom Wednesday episode, Derek and Chip explore how mentorship evolves when experience meets curiosity. Drawing on stories from Airbnb, intergenerational leadership, and lessons from unlikely teachers, Chip shows why the best mentors are still learning.In this conversation, you’ll discover:• Why great mentorship is a two-way exchange, not top-down advice• How modern elders learn alongside younger generations• The difference between a librarian...
2026-02-1120 minThe Midlife ChrysalisWhy Wisdom Matters More Than Knowledge in Midlife | Eric WeinerWe’re surrounded by information but many of us still feel unsure about how to live well. This episode gently explores why midlife pulls us toward wisdom, not more answers. Chip Conley is joined by bestselling author Eric Weiner (The Geography of Bliss, Man Seeks God, The Socrates Express), a curious guide who’s spent years learning from philosophers, cultures, and lived experience. Together, they talk about what ancient wisdom can teach us about modern life—especially when certainty starts to fall away. In this conversation, you’ll hear:Why midlife naturally...
2026-02-0953 minThe Midlife ChrysalisStuck at 50? How to Make a Midlife Career Change Without Starting OverWhat 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 Ghel 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...
2026-02-0432 minThe Midlife ChrysalisHow a Panic Attack Sparked a Midlife Awakening | Dan HarrisHe 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 s...
2026-02-0250 minThe Midlife ChrysalisWhen Cancer Forces a Life Reset in Midlife | Caryn LermanCancer 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 b...
2026-01-3058 minThe Midlife ChrysalisWhy Rituals Matter More Than Routines in MidlifeWhat 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 a...
2026-01-2818 minThe Midlife ChrysalisHow Ritual, Awe, and Community Bring Midlife Back to Life | Christine SperberIn 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...
2026-01-261h 04The Midlife ChrysalisThe Bonus Years: Midlife Is About Reinvention Not Retirement | Pam McLeanMidlife 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 h...
2026-01-2347 minThe Midlife ChrysalisMidlife Isn’t Falling Apart – It’s a TransformationMidlife 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 th...
2026-01-2134 minThe Midlife ChrysalisGavin Newsom on Leadership, Identity, and Becoming YourselfWhat 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...
2026-01-1957 minThe Midlife ChrysalisCould Golden Girls–Style Living Be the Future of Midlife Housing?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...
2026-01-1427 minThe Midlife ChrysalisAging While Black: Paying the Price of a Broken System | Ray JetsonAging 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...
2026-01-1259 minThe Midlife ChrysalisHow Conscious Capitalism Changes the Way Leaders Think | Rand StagenMost 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 infi...
2026-01-091h 01The Midlife ChrysalisThe Success Treadmill Is Real: Here’s How to EscapeIn 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 si...
2025-12-2421 minThe Midlife ChrysalisThe Hidden Cost of Playing It Safe in Midlife | Dr. Margie WarrellWhat if the real risk in midlife isn’t change but staying comfortable?In this episode of Midlife Chrysalis, Chip Conley sits down with Dr. Margie Warrell, global expert on courage and bestselling author of The Courage Gap, to explore why so many smart, capable people feel stuck and how to move forward with clarity and bravery. Drawing from her journey from a rural Australian farm to the world stage, Margie shares powerful insights on courage, reinvention, and choosing growth over safety. ...
2025-12-2252 minThe Midlife ChrysalisInside the Messy Middle: What Actually Drives Transformation in MidlifeFeeling stuck in midlife? You might be in your chrysalis, not a crisis.In this Wisdom Wednesday episode, Chip Conley breaks down why midlife often feels confusing and heavy, and why that “messy middle” is actually the beginning of real transformation. Chip shares:• The three stages of every transition and where most people get stuck• What really happens inside the messy middle• Why men and women experience midlife so differently• How transitional intelligence (TQ) helps you move forward with clarity
2025-12-1723 minThe Midlife ChrysalisHow Curiosity Fuels a Longer, Healthier LifeWhat if the secret to living longer isn’t in your genes… but in your mindset?In this Wisdom Wednesday episode, Chip Conley reveals the surprising research showing how a simple shift in how we think about aging can add years—yes, actual years—to our lives. From Becca Levy’s longevity findings to Carol Dweck’s growth-mindset principles, Chip breaks down why curiosity, openness, and lifelong learning may be the real fountain of youth. You’ll learn why “I’m too old to…” is one of the most dangerous beliefs we carry, how...
2025-12-1016 minThe Midlife ChrysalisGrowing Whole: Why Midlife May Be the Best Time of Your LifeWhat if midlife is actually the start of your happiest years?In this episode, Chip Conley and Derek Gehl break down why life often gets better after 50, from rising emotional intelligence and deeper wisdom to feeling more like your true self. Chip explains why “growing whole” matters more than “staying young,” how Carl Jung’s insights can reshape your mindset, and why a pro-aging outlook can change your health, relationships, and purpose.If you want a fresh, hopeful take on midlife, don’t miss this conversation. Watch now....
2025-12-0316 min
The Midlife ChrysalisFrom Experience to Wisdom: A Midlife Conversation That MattersIn the very first episode of Wisdom Wednesdays, Chip Conley and Derek Gehl sit down for a thoughtful, honest conversation about what wisdom really means in midlife. Chip shares the down-to-earth definition that guides his life and talks about the small, consistent practices that help him turn everyday experiences into something meaningful.If you’re ready for conversations that spark growth, clarity, and courage…▶️ Start with Episode 1 and begin your wisdom journey with us. Timestamps:00:00 Intro00:22 Welcome to Wisdom Wednesdays01:37...
2025-11-1917 minThe Midlife ChrysalisRainn Wilson: Finding the Soul Beyond the SpotlightWhat if the path to a meaningful life had nothing to do with fame or success and everything to do with service and soul?In this captivating conversation, Rainn Wilson opens up about his transformation from Hollywood ego to spiritual seeker, sharing how faith, meditation, and humility helped him rediscover purpose beyond the spotlight. Together with Chip Conley, he explores why midlife can be a sacred turning point when the soul finally takes the lead.👉 Watch now to learn how Rainn’s journey can help you reconnect with your own s...
2025-10-3153 minThe Midlife ChrysalisArthur Brooks on How to Break Free from the Striver’s Curse in MidlifeWhat if everything you’ve been taught about happiness and success is upside down?In this episode of Midlife Chrysalis, Chip Conley talks with Arthur Brooks, Harvard professor, bestselling author, and former French horn prodigy, about his remarkable journey from the concert stage to the world of behavioral science. Together, they unpack why strivers burn out, how our brains shift from fluid to crystallized intelligence, and the simple formula that can turn midlife from a crisis into a transformation.Don’t miss this inspiring conversation. Listen now and start reth...
2025-10-081h 10The Midlife ChrysalisElizabeth Gilbert’s Untold Story of Love and AddictionHow do you survive when the person you can’t live without begins to destroy you?In this powerful episode of Midlife Chrysalis, Elizabeth Gilbert joins Chip Conley to share the raw story behind her new memoir, All the Way to the River. She opens up about walking alongside her partner through addiction and relapse, confronting her own patterns of codependency, and finding healing through recovery and surrender. It’s an honest, unfiltered look at love, loss, and what it really takes to stand on your own two feet.Tune...
2025-09-101h 02The Midlife ChrysalisAging Boldly and Living on Your Own Terms with Karen WalrondAuthor, 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 somet...
2025-08-201h 00The Midlife ChrysalisWhat Burning Man Teaches Us About Aging, Identity & Legacy | Marian GoodellWhat 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...
2025-07-1056 minThe Midlife ChrysalisIntroWelcome to the very first episode of The Midlife Chrysalis!Chip Conley kicks off this amazing podcast by redefining midlife. It’s not as a crisis, but a powerful chrysalis for transformation.He shares his own wild journey and reveals why your 40s, 50s, and beyond can be the most meaningful years of your life. Plus, get a sneak peek at upcoming guests like Maria Shriver, Brian Chesky, Gavin Newsom, and more. If you're ready to reinvent yourself and thrive in midlife, this is yo...
2025-06-0203 min
Grey Matter with Michael KrasnyViable Hospitality and Valuable Wisdom from Hotelier Chip ConleyMichael Krasny began this episode with author, hotelier and long-time wisdom seeker Chip Conley, who was in Baja, talking about the terrible fires in Los Angeles and what if any lessons can be learned from them. They spoke of wisdom seeking and Conley of the metaphor for our lives of a rental car as well as his ongoing struggle with cancer, which he calls his teacher. Krasny brought up wrong headed views of cancer that place too much blame on the individual self and they spoke of environmental and so-called lifestyle effects tied to it and then proceeded to...
2025-01-161h 06
Tango Alpha Lima PodcastModern Elder Academy founder Chip ConleyBRAVO ZULUHost Stacy Persall welcomes her two new co-hosts, Joe Worley and Adam Marr to their first episode, which the trio kicks off with celebration of three American Legion Posts who are making big differences in their local communities.GUESTSuccessful hospitality entrepreneur and bestselling author Chip Conley is on a quest to reframe our relationship with aging. He founded the Modern Elder Academy with a mission to foster intergenerational mentoring as a ‘modern elder.’ Conley talks about his experience as a 'modern elder' at AirBnB, how he embraces mid-life and how thes...
2024-03-051h 08
On WisdomThe Wisdom of a Modern Elder (with Chip Conley)Though there is a lot of talk about diversity in the workplace, “age diversity” is often overlooked. Might there even be an emerging mission-critical role for wise elders in the world’s most cutting-edge tech companies? Hospitality maverick and Airbnb Strategic Advisor Chip Conley joins Igor and Charles to discuss the U-Curve of happiness, the surprises and challenges of mentoring billionaire CEOs and State Governors, the potential of intergenerational housing, the emergence of a new generation of wisdom workers, and his new project to build the world’s first midlife wisdom school - The Modern Elder Academy. Igor seeks new solu...
2020-04-0753 min