The Midlife Chrysalis
The Midlife Chrysalis is a one-hour podcast hosted by Chip Conley, bestselling author of Learning to Love Midlife and founder of MEA (Modern Elder Academy). Chip and his high-profile guests – including Maria Shriver, Hoda Kotb, Elizabeth Gilbert, Michael Franti, and more – dive into raw, vulnerable conversations about the profound transitions they’ve experienced in midlife. Listeners get a rare look at how even the most successful individuals have to navigate life’s pivotal changes – and gain practical wisdom they can apply in their own lives for a more fulfilling and purposeful next chapter.
Episodes
You Got Everything You Wanted. Now What? | Edward Sullivan
What 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 achieve
Follow the Energy, Not the Career Script | Arun Gupta
Your 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
How 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 ex
How to Talk to People You Profoundly Disagree With | Shamil Idriss
How 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 r
Why Retirement Is the Wrong Goal | Ken Dychtwald
Midlife 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
Why 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 thi
How Psilocybin Can Change Your Life After 40 | Neil Markey
Could 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
Your Brain Is Lying to You About Happiness | Dr. Laurie Santos
We'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&
Why High Achievers Still Feel Like Imposters
Do 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
The Biggest Lies We've Been Told About Aging | Ashton Applewhite
In this eye opening conversation, bestselling author and aging activist Ashton Applewhite challenges everything we think we know about growing older. She reveals why many of our fears about aging come from culture, not reality, and explains how getting older can bring more freedom, confidence, and purpose.In this episode, you'll learn:Why ageism is one of the last socially accepted forms of pr
Why Your 70s Can Be Your Most Meaningful Years | Dr. Philip Pizzo
What 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 ex
Don't Save It for the Funeral: The Power of a Social Eulogy
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 thi
The Hero’s Journey: Crossing the Threshold from Stagnation to Generativity | Pat Whitty
At 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
The Power of Play in Reinventing Your Life | Kristine Michie & JD Schramm
Play 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
Can AI Ever Be Wise? Knowledge vs. Human Experience
Can 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
The Science Behind a Better Midlife| Dr. Margie E. Lachman
Midlife 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 o
How to Build a Life You Don't Want to Retire From | Stephen Herman & Evelyn Neaman
Retirement isn't the end of your career. It's the beginning of the life you've been preparing for.In this episode, filmmaker and former lawyer Stephen Herman and criminal justice reform leader Evelyn Neaman share the personal experiences that inspired them to rethink retirement and help others navigate this major life transition with purpose and confidence.Together, they explore:Why so
What Your Future Self Wants You to Know About Life
Have you ever wondered what your 80 year old self would tell you today?In this episode, Derek and Chip talk about aging, relationships, purpose, and the life lessons that only become clear with time. Through a powerful exercise imagining a conversation with his future self, Chip shares the insights that have reshaped how he thinks about success, love, health, and what truly matters.In this episode
How Time Away Can Change Your Future | DJ DiDonna
Burnout, 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 wo
The Soul of Money: Why Life Gets Better After 50 | Lynne Twist & Sara Vetter
Can 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-chan
How Wise People Handle Uncertainty
Uncertainty 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 ongoi
The Skills That Will Matter Most in the AI Era | Chris Shipley & Scott Barry Kaufman
AI 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
The Biggest Myth We Believe About Aging | Dr. Michael Gurven
Most 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
Stop Trying to Fit In: The Hidden Gift of Aging
What 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,
Can Your Mind Change How You Age? | Ellen Langer
Aging 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 acc
Why We Spend Years Chasing Things We Don't Really Want | Alain de Botton
You 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 ou
The Real Problem Isn't Aging. It's Resisting It.
What if the biggest challenge of aging isn't getting older, but learning to stop fighting it?In this Wisdom Wednesday, Chip and Derek explore one of the most important lessons of midlife: learning to work with your body instead of fighting it.Some of Chip's key insights include:Why the body often signals what we need long before we pay attentionHow slowing down helps us reconnect with our
Science Says Aging Can Make You Happier | Laura Carstensen
The 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 youn
Why So Many of Us Feel Like We Don't Belong | Pádraig Ó Tuama
What 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 l
When Success Isn't Enough: Finding Purpose in Midlife
Many 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 o
What Comes After You've Achieved Everything? | Bill George
He 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 l
Stop Beating Yourself Up and Listen to This | Kristin Neff
Most of us are far kinder to other people than we are to ourselves and according to leading self-compassion researcher Kristin Neff, that may be one of the biggest reasons we struggle with stress, burnout, anxiety, and self-doubt.In this episode, Kristin shares how discovering self-compassion through Buddhism and mindfulness changed her life during a difficult period of divorce, uncertainty, and i
Why 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 prese
What Research Reveals About America’s Midlife Crisis | Frank Infurna
Why do so many people feel overwhelmed, lonely, and unhappy in midlife?Conley sits down with leading midlife researcher Frank Infurna to explore why so many middle-aged adults are struggling with stress, mental health challenges, and declining well-being, especially in the United States.Drawing from years of research on aging and happiness, Frank explains why Americans report higher levels of lone
The Truth About Becoming Miserably Successful | Debjani Biswas
What 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 engin
The Millennial Midlife Crisis Won't Look Like You Think
Are 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 mindse
The Decade Game That Can Transform Your Future | Carolyn Buck Luce
Many 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 power
What 88 Years of Research Revealed About Happiness | Robert Waldinger
For nearly 90 years, researchers tracked one question: what actually makes people happy, healthy, and fulfilled as they grow older?In this episode, Chip sits down with psychiatrist, Zen teacher, and Harvard study director Robert Waldinger to explore what 88 years of research can teach us about relationships, aging, purpose, and emotional well-being.Together, they unpack:Why strong relationships pr
How to Turn Anxiety Into Wisdom, Clarity, and Resilience
Anxiety, 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 uncert
Why Deep Listening is the Key to Transformation | Gail Larsen
The 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 thousand
Why Success Alone Will Never Fulfill You | Brad Stulberg
You hit your biggest goals… and still feel empty?In this episode, performance expert and bestselling author Brad Stulberg breaks down why success alone doesn’t fulfill us and what actually does.Drawing from his own experience with burnout, mental health struggles, and years of research, Brad shares a powerful new way to think about excellence, purpose, and what it really means to live well.Here ar
Why So Many Successful People Struggle With Retirement
Why 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 ambiti
Why Modern Life Is Terrified Of Death | Ben Yalom
What do you do when the version of yourself you built for decades no longer fits your life?In this conversation, Chip sits down with therapist and former theater director Ben Yalom for a warm, honest discussion about reinvention, grief, aging, identity, and the courage it takes to change direction in midlife.After spending years in experimental theater, Ben found himself at a crossroads during COV
Why Facing Mortality Changes How You Live | Dr. Kerry Burnight
In this episode, I sit down with gerontologist Kerry Burnight, who has spent decades working with people in their 80s, 90s, and even 100s. And what she’s learned might completely change how you think about aging, and how you choose to live right now.Kerry introduces a powerful idea called joyspan, the missing piece between how long you live and how well you live. And the truth is, most people are
What Keeps You Together When Everything Falls Apart?
What happens when life changes all at once?In this deeply emotional conversation, Chip opens up about one of the hardest seasons of his life: facing stage 3 cancer again while grieving the loss of his mother, navigating relationship changes, caring for his aging father, and trying to hold onto purpose through it all.But this episode isn’t about giving up. It’s about what keeps us going when life f
Feeling Stuck at 50: How to Find Your Magic and Start Again | Matt Ross
The 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 fo
What Horses, Death, and Nature Taught Me About Being Human | Kelly Wendorf
What 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 fee
AI vs Humans: The One Skill AI Still Can’t Replace
AI 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 world
The New Way Women Over 50 Are Choosing to Live | Elizabeth White
In this powerful conversation, Elizabeth White, author of 55, Underemployed, and Faking Normal, shares how losing everything during the recession led her to uncover a hidden crisis affecting millions of women over 50… and a bold new solution.Here’s what you’ll learn:Why financially stable women are quietly slipping into insecurityWhy housing, not healthcare, is the real pressure point in midlifeHo
You Were Never Meant to Think This Way | Angus Fletcher
In this episode, Angus Fletcher, a professor, author, and advisor to U.S. Army Special Operations, explains why so many people feel stuck even when life looks “right,” and what important human abilities we slowly lose as we get older without noticing.Instead of chasing more knowledge, Angus points to a different path, one built on the natural abilities we all had as children but were slowly traine
Why Success Stops Making You Happy After 40
You 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 d
You Did Everything Right… So Why Does It Feel Wrong? | Jill Nykoliation
You can have a career, success, and still feel like something is missing.In this episode, Jill Nykoliation, former CEO of a globally recognized branding agency turned executive coach, shares how she walked away from a high-level career to rediscover who she really is, and why that shift changed everything.Here’s what you’ll learn:Why success can feel empty (and what it’s really telling you)The par
The Real Reason You’re Aging Faster Than You Should | Dr. Florence Comite
You’re not aging the way you think you are, and that changes everything.In this episode, Chip sits down with Dr. Florence Comite, Yale-trained physician, longevity expert, and author of Invincible, to explore a smarter, more personal approach to health and aging.Blending science with a powerful personal story, she challenges everything we think we know about living longer.Here’s what you’ll learn:
Take a Month Off and See Who You Become
What 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
How to Heal Trauma in Your Body and Mind | Rebecca & Jaimie
In 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 psycholo
Stop Living on Autopilot. Start Living for Real | Bonnie Wan
Most people don’t realize they’re living someone else’s life until it’s too late.In this episode, Chip Conley sits down with Bonnie Wan, a renowned brand strategist and author of The Life Brief, who has spent decades studying human behavior, and now helps people redesign their lives with clarity and intention.Through her “Life Brief” method, people learn how to cut through the noise and make decis
Knowledge Won’t Save You. Curiosity Will
You don’t stay relevant by knowing more. You stay relevant by staying curious.In this episode of Wisdom Wednesday, Chip Conley joins Derek Gehl to break down why curiosity, not experience or intelligence, is the real edge in midlife and beyond.Here’s what stands out:Curiosity is the antidote to irrelevanceAsking better questions beats having the right answersMidlife requires a shift from knowledge
She Quit a 30-Year Career to Help Others Rebrand Their Lives | Robin Fisher Roffer
Midlife might be the moment everything finally starts to make sense.In this episode of The Midlife Chrysalis, Chip sits down with branding expert Robin Fisher Roffer, who spent over 30 years shaping major brands, to explore how those same principles can help you reinvent your life.Robin shares her own powerful transition, stepping away from a successful career to start a whole new chapter, and wha
Feeling Lost? Use Inner Tracking to Find Your Path| Lee Johnson
Midlife can feel confusing, off track, or quietly unsettled, and you’re not the only one feeling it. In this episode of Midlife Chrysalis, Lee Johnson, a mindfulness guide and teacher, shares his journey from ranch life to guiding others through mindfulness and “inner tracking,” offering a grounded and deeply human perspective on finding your way without a clear plan. Here’s what you’ll take away:
Stuck Between Aging Parents and Grown Kids in Midlife?
You’re taking care of your parents. You’re supporting your kids. But who’s taking care of you?In this Wisdom Wednesday episode, Derek Gehl sits down with Chip Conley to unpack the reality of the sandwich generation and why midlife can feel more overwhelming than ever. Chip shares key insights on:• The real emotional cost of caregiving• Why this stage of life feels heavier today• How to build a sup
Leading in Chaos: How to Stay Grounded Under Pressure | Amy Elizabeth Fox
What if the chaos in your life isn’t the problem… but the turning point?In this episode, Amy Elizabeth Fox, leadership expert and co-founder of Mobius, explains why today’s pressure, uncertainty, and stress are actually pushing us to grow in a deeper way. Through her work with top executives and her own life story, she shows what it really takes to lead and stay grounded when everything feels unst
She Told 80,000 Employees the Truth She Hid Her Entire Life | Katherine Dudtschak
She had the perfect life - career, family, success - and a secret she kept hidden for decades.In this episode, Katherine Dudtschak, a former top banking executive, opens up about coming out at 50, telling 80,000 employees, and risking everything to finally live in alignment with who she truly is.It’s an honest, deeply human story about what happens when you spend years living the life you’re “supp
Why So Many Men Lose Friends in Midlife (And How to Fix It)
What if the biggest factor for a longer, happier life isn’t health, but friendship?In this Wisdom Wednesday episode, Chip Conley joins Derek Gehl to explore why so many people, especially men, struggle with connection in midlife, and how to change that.Here’s what you’ll learn:Why friendship is the #1 predictor of longevityThe difference between real vs transactional relationshipsWhy men often lac
Death, Belonging, and What It Means to Be Human | Sebastian Junger
He was bleeding out… and didn’t even know he was dying.In this powerful conversation, war journalist and bestselling author Sebastian Junger shares the moment he came face-to-face with death and what he discovered on the other side.From a sudden internal hemorrhage to a near-death experience that challenged everything he believed, Junger takes us deep into the edge between life and death… and back
How an Anarchist Built One of America’s Most Unique Businesses | Ari Weinzweig
Anarchism isn’t chaos. It might be the key to better leadership.In this thought-provoking episode, Chip speaks with Ari Weinzweig, co-founder of Zingerman’s, a company that grew from a $22,000 deli into an $80M family of businesses built on an unconventional idea: trust people, give them dignity, and rethink hierarchy.Ari shares the surprising philosophy that shaped Zingerman’s culture and explain
Men vs Women in Midlife: The Struggles No One Warns You About
Most 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,
Why Love Requires Skills Most People Never Learn | Terry Real
Why 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 conversa
Pete Holmes on Psychedelics, God & Finding Meaning in Midlife
The 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 con
Midlife Pit Stop: Refuel Before the Next Chapter
What 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 refu
Designing the Second Half of Life: Meaning, Curiosity, and Becoming | Bill Burnett & Dave Evans
Most 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 “figur
Why You Keep Repeating the Same Conflict Patterns | Diana Chapman
Real 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
From Ego to Soul: Rewriting the Second Half of Life
The 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
Mortality Was My Wake-Up Call | Dr. Brad Jacobs
What if the real key to longevity isn’t a biohack but a wake-up call?In this episode, Dr. Brad Jacobs, longevity expert, integrative medicine pioneer, and former UCSF professor, shares what truly helps us thrive in midlife.After losing his father to cancer at 27, Brad made it his life’s work to understand how we can live longer and better.In this episode, we explore:What actually extends your life
Why Midlife Feels Like Exile And Why That’s a Gift | David Whyte
In this episode of Midlife Chrysalis, poet and philosopher David Whyte explores why midlife often feels like losing your way and why that experience may be exactly what opens the door to deeper meaning.Drawing on poetry, psychology, and Dante’s famous “dark wood,” David explains how moments of uncertainty can become powerful turning points in our lives.In this conversation, he shares:Why midlife c
Letting 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 conve
Greg Louganis: Olympic Gold, Public Masks, Private Truth
What happens when the world sees a champion… but you’re still figuring out who you are?In this episode of The Midlife Chrysalis, Olympic legend Greg Louganis opens up about the life behind the gold medals and the deeper journey beyond fame. From childhood wounds and public adoration to living with HIV and facing mortality at 28, Greg shares how his identity has evolved over decades.You’ll hear:• H
Midlife and the Moral Pressure of Limited Time | Kieran Setiya
Midlife can feel unsettling even when life looks successful on paper. This episode explores why that discomfort appears and how it can become a source of clarity rather than crisis. Our guest is Kieran Setiya, MIT philosophy professor and author of Midlife: A Philosophical Guide. Drawing from philosophy and lived experience, he offers a calm, deeply human way of understanding regret, time, ambitio
What a Cancer Diagnosis Teaches You About How to Live
What 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
From Ambition to “I’m Enough” | Brian Chesky
In 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 fr
Your Brain on Art: Why Midlife Needs Creativity More Than Ever | Susan Magsamen & Ivy Ross
Midlife 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,
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