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
MEA Film Fest: Come for the Movies, Stay for the Connections
Watch 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 o
From Nike CEO to Starting Over at 65: John Donahoe’s Reinvention
After decades at the top, John Donahoe found himself starting over at 65.John has led eBay, ServiceNow, and Nike. But some of his most important lessons came from burnout, failure, and the difficult transitions between success and what comes next.In this deeply personal conversation, John shares:Why stepping away at 55 changed the way he saw success and himselfWhat 50 wise elders taught him about
When the Life You Built Is No Longer Enough | Caroline Myss
Midlife 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 a
What 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 discov
He Died 11 Years Ago. Their Relationship Never Ended. | Lucy Kalanithi
Eleven 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 mo
Why Life Can Get Harder and Happier After 50 | Jonathan Rauch
Jonathan Rauch had reached the top of his career, yet each year he felt less satisfied. Then came the loss of his parents, his job, and a startup he had tried to build. To his surprise, his sense of contentment began to grow.Rauch is a journalist and the author of The Happiness Curve, The Constitution of Knowledge, and Cross Purposes. He joins Chip Conley to explore what his personal experience an
The Hardest Leadership Lesson: Let Someone Else Be the Hero
Being 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 help
What Changes When You Finally Let Go of Control? | Thomas DeLong
Success 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
Let Life Lead: A Different Way to Navigate Midlife | Nic Askew
Sometimes the most powerful way forward begins by doing less.Filmmaker Nic Askew has spent more than two decades capturing what happens when people stop performing and simply allow themselves to be seen. Through his Soul Biographies, he has discovered a different way of approaching connection, identity, and life itself.In this episode, Nic explores:Why “starting with nothing” can reveal what effor
Be Useful, Not Youthful: The Secret to Aging Well
At 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 invisib
Can Your Beliefs Actually Change How You Age? | Shawn Achor
We’re taught to expect decline as we get older. But the science tells a far more hopeful story.In this episode, bestselling author and positive psychology expert Shawn Achor joins us to explore how our beliefs can shape the way we age. Drawing from his new book, The Power of Beliefs, groundbreaking research, and his own midlife experience, Shawn reveals why getting older can bring new opportunitie
He Spent 10 Years Filming the World’s Oldest People | Sam Green
What can the world’s oldest people teach us about time, aging, and being alive?Academy Award nominated filmmaker Sam Green spent 10 years filming people who held the title of the world’s oldest living person. His documentary The Oldest Person in the World began as a curiosity but became a deeply personal exploration of mortality, connection, and how we use the time we have.In this episode, Sam sha
Why Birthdays Matter More as We Get Older
Why 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 a
Surfing at 87, Writing at 91: James Flaherty’s Rules for Life
At 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. G
From Role to Soul: Who Are You Without What You Do? | Connie Zweig
Aging 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
You Can’t Rush Grief: Learning to Feel What We’ve Lost
Some 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 spa
What Happens After You Achieve Your Biggest Dream? | Paul Harris
What happens when the identity you've spent your entire life building suddenly disappears?Former South African international cricketer Paul Harris reached the highest level of his sport, but retiring at just 33 forced him into an even bigger challenge: discovering who he was beyond cricket. In this powerful conversation, Paul shares the emotional reality of life after professional sports and t
From Doing to Being: The Power of Presence | Teddi Dean
Sometimes 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 stillnes
Curiosity Is the Secret to a Richer Life
Happiness 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
We’re Living Longer. Why Isn’t Society Ready? | David Sinclair
The 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
From Achievement to Fulfillment: Building Your Life 3.0 | Seth Streeter
Success can look impressive on the outside and still leave you feeling like something is missing.Seth Streeter, co-founder of Mission Wealth, spent decades building a successful career while constantly pushing himself to achieve more. But after personal crisis, health struggles, and a major identity shift, he began questioning what success was really for.In this episode, Seth shares his journey fr
Could 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 f
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
Recommended
McKinsey on Consumer and Retail
megahired.com
Hard Knocks Podcast
Effective Weight Loss for Moms | High protein, Strength Training, Lose Weight, Meal Planning, Fat Loss, Healthy Habits
The Human-Animal Connection - Pet Life Radio Original
The Daily
World News Tonight with David Muir
The Joe Rogan Experience
English Vocabulary Help
TED Talks Daily
Learn English B1 with Daily News | English Listening Practice
Talk About Talk - Executive & Leadership Communication Skills
