The Midlife Chrysalis

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...

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...

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...

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 thinking Wisdom now matters more than knowledge in an AI-driven w...

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 insecurity Why housing, not healthcare, is the real pressure point in midli...

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 tra...

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 direction Why achievement alone doesn’t lead to fulfillment The hidden trap...

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) Th...

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 le...

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...

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 psych...

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 de...

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 irrelevance Asking better questions beats having the right answers Midlife requires a shift from kno...

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...

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 awa...

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...

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 uns...

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 “su...

What if the biggest factor for a longer, happier life isn’t health, but friendship? In this Wisdom Wednesday episode, Chip Conley joins D erek 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 longevity The difference between real vs transactional relationships Why men oft...

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 ba...

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 exp...

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 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 conv...

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...

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 ref...