The Midlife Chrysalis

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...

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 ongo...

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 t...

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 livi...

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...

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 a...

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 o...

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 attention How slowing down helps us reconnect with...

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...

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 is How poetry helps us naviga...

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 i...

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...

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...

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 longer How flow states help us become fully...

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 lo...

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 engi...

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 minds...

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 powe...

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...

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 un...

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 thou...

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...

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 amb...

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 C...

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 ar...