The Midlife Chrysalis

In the very first episode of Wisdom Wednesdays, Chip Conley and Derek Gehl sit down for a thoughtful, honest conversation about what wisdom really means in midlife. Chip shares the down-to-earth definition that guides his life and talks about the small, consistent practices that help him turn everyday experiences into something meaningful. If you’re ready for conversations that spark growth, clari...

Midlife isn’t a crisis. It’s your greatest awakening. In this inspiring episode, gerontologist and coach Barbara Waxman redefines aging through the lens of “Middleessence,” a stage of growth, purpose, and renewal. She reveals how to reclaim energy with her Energy Audit, why mindset matters more than genetics for longevity, and how lifestyle medicine helps you live undiminished at every age. ✨ Lea...

What if aging isn’t about decline, but about becoming more alive than ever? The bestselling author and spiritual teacher Mark Nepo opens up about how surviving cancer reshaped his entire understanding of life, creativity, and purpose. He reveals the wisdom behind The Fifth Season, a time in life when the inner world begins to shine brighter than the outer one, and shares how to live and create wit...

🔥 One night on air changed everything for Tamsen Fadal. She was at the top of her game as a TV anchor when she suddenly started forgetting words and sweating through live broadcasts, without realizing she was entering menopause. That moment became the turning point that led her from journalism to advocacy. In this conversation, Tamsen shares how she turned confusion into purpose, launching The M...

What if awe was the secret ingredient to happiness? 🌿 In this episode, I sit down with UC Berkeley psychologist Dacher Keltner to explore how awe, compassion, and moral beauty can transform the way we live and age. We dive into the science of wonder — from the power of collective joy to how simple “awe walks” can boost your health, purpose, and connection. ✨ Join us as we uncover why we’re truly...

What happens when one of the NFL’s most celebrated athletes walks away from fame, fortune, and the life everyone else wanted for him? In this powerful episode, Ricky Williams, now known as Errick Miron, opens up about his transformation from Heisman Trophy winner to healer, teacher, and astrologer. He shares how depression, self-discovery, and spirituality reshaped his identity and helped him find...

What if the path to a meaningful life had nothing to do with fame or success and everything to do with service and soul? In this captivating conversation, Rainn Wilson opens up about his transformation from Hollywood ego to spiritual seeker, sharing how faith, meditation, and humility helped him rediscover purpose beyond the spotlight. Together with Chip Conley, he explores why midlife can be a sa...

What if the worst thing that ever happened to you became the very thing that set you free? 🌱 In this deeply moving episode, Dr. BJ Miller—physician, amputee, and palliative care visionary—shares how a near-fatal accident in college transformed his understanding of life, loss, and what it really means to live fully. From his journey through unimaginable pain to founding Mettle Health, BJ reveals h...

Ever wondered what it really means to start over when the world thinks you’ve peaked? In this episode, Daniel Pink, bestselling author of Drive and The Power of Regret, reveals why midlife isn’t a crisis but a creative turning point. He talks about becoming a beginner again after 50, how regret can guide us toward what truly matters, and why lasting motivation comes from autonomy, mastery, and pur...

What happens when the person you love most slowly begins to disappear before your eyes? In this deeply emotional and inspiring conversation, Emma Heming Willis opens up about life with Bruce Willis following his diagnosis of frontotemporal dementia and how she turned heartbreak into purpose. Joined by Helen Christoni, co-founder of Make Time Wellness, the two reveal why women’s brain health is so...

What if everything you’ve been taught about happiness and success is upside down? In this episode of Midlife Chrysalis, Chip Conley talks with Arthur Brooks, Harvard professor, bestselling author, and former French horn prodigy, about his remarkable journey from the concert stage to the world of behavioral science. Together, they unpack why strivers burn out, how our brains shift from fluid to cry...

What happens when a world-famous photographer nearly loses everything — and turns it into a movement redefining aging? In this powerful conversation, David Stewart shares his journey from shooting Vogue covers and working with Andy Warhol’s circle, to battling a life-threatening autoimmune disease that forced him to rethink everything. Out of crisis came transformation — and the creation of Ageist...

What happens when a bestselling writer and a former corporate executive dive deep into life’s second half? In this powerful conversation, Anne Lamott and Neal Allen share raw, funny, and moving stories about midlife transformation, spiritual awakening, recovery, and how to finally silence that relentless inner critic. From faith and writing to intimacy, aging, and finding purpose, their wisdom wil...

What if the most painful disruptions in life—illness, job loss, divorce, or even an empty nest, were actually the keys to growth? Bestselling author Bruce Feiler shares how “life quakes” shake up our stories and push us to rewrite them. From his own battle with cancer and family upheaval to studying hundreds of life transitions, Bruce reveals why resilience is a skill, not a trait, and how rituals...

How do you survive when the person you can’t live without begins to destroy you? In this powerful episode of Midlife Chrysalis, Elizabeth Gilbert joins Chip Conley to share the raw story behind her new memoir, All the Way to the River. She opens up about walking alongside her partner through addiction and relapse, confronting her own patterns of codependency, and finding healing through recovery a...

What happens when one of America’s most celebrated pastors dares to question everything? In this unfiltered conversation, Rob Bell, once dubbed the “punk rock pastor” and author of the explosive bestseller Love Wins, opens up about the controversy that made him Christianity’s most talked-about heretic, why he walked away from his megachurch at the height of fame, and how midlife pushed him to rein...

What if aging wasn’t about slowing down—but about leveling up? In this powerful conversation, Marc Freedman, founder of Encore.org (now CoGenerate), unpacks the surprising history of retirement, why communities like Sun City reshaped how we see aging, and how we can flip the script on what it means to grow older. From encore careers to intergenerational mentorship, Marc shows why midlife is no dea...

Author, speaker, and “Radiant Rebel” Karen Walrond joins Chip Conley for a warm, inspiring conversation on how to age with joy, live on your own terms, and keep your spark alive. From growing up between Trinidad and the U.S., to leaving engineering and law for a creative life, Karen’s story is full of bold choices and unexpected turns. She shares cultural insights on aging, how to break free from...

What happens when a Harvard scholar, devoted Mormon, and mother of a child with Down syndrome begins to hear psychic messages—and decides to tell the truth no matter the cost? In this powerful conversation, Martha Beck shares how leaving her religion, embracing polyamory, and facing her deepest fears led her to a life of radical integrity, joy, and healing. If you’ve ever felt stuck, out of alignm...

What happens when a self-made billionaire steps away from the company she built and faces the big question: What’s next? In this inspiring episode, the founder of Spanx opens up about her journey from door-to-door sales to creating a global brand, the emotional challenges of selling her company, and how she’s redefining success, purpose, and identity in midlife. It’s a raw and uplifting conversati...

What if midlife isn’t a breakdown—but a breakthrough? In this powerful conversation, world-renowned writer Pico Iyer shares the surprising lessons he’s learned from 50 years of friendship with the Dalai Lama, losing everything he owned, and finding stillness in the chaos. From walking away from success in New York to building a soulful life in Japan, Pico reveals how true freedom comes not from ha...

What happens when a successful actor—and the son of a Hollywood legend—hits midlife and starts asking deeper questions? In this powerful episode, Scott Eastwood opens up about building his own identity beyond Clint Eastwood’s shadow, what 40+ films have taught him, and why he’s now prioritizing purpose over fame. He reflects on masculinity, mentorship, mistakes, and what it really means to grow wi...

What happens when one of the most thoughtful voices in public life hits a wall? In this deeply personal conversation, Krista Tippett opens up about burnout, walking away from success, and rediscovering joy in midlife. From letting go of exhaustion to falling in love again, she shares the hard-won wisdom that’s reshaping how she lives, works, and loves. It’s a moving reminder that it’s never too la...

What if your so-called “midlife crisis” was actually a doorway to reinvention? In this powerful conversation, Burning Man CEO Marian Goodell joins Chip Conley to explore how the radical spirit of Burning Man offers surprising lessons on aging, identity, leadership, and legacy. From embracing impermanence to finding purpose without a script, this episode is a deep dive into how midlife can be your...

What does it really take to start over at 69? In this inspiring episode, Whole Foods founder John Mackey shares how psychedelics, purpose, and love reshaped his path after selling to Amazon. From ego death to building Love Life wellness centers, he opens up about business regrets, spiritual breakthroughs, and midlife transformation. You'll learn how conscious capitalism evolves with age—and why lo...