The Midlife Chrysalis

What happens when Don Lemon gets truly unfiltered?

In this heartfelt, funny, and deeply honest conversation, Don opens up about aging with confidence, coming out in midlife, letting go of old shame, and the freedom that comes from no longer needing anyone’s approval. We talk about identity, love, sex, wisdom, and why his mantra “old people be knowing” captures the real gift of growing older.

Don also reflects on the state of medi...

Grief isn’t just an emotion, it’s energy that lives in the body until we face it.

I sit down with Meghan Jarvis, a trauma therapist and grief mentor who’s helped countless people find their way through loss. Meghan shares her own story of heartbreak, how grief and trauma intertwine, and the six simple practices she teaches to move that heavy energy through the body and back toward healing. We also talk about midlife transitions,...

What if everything you’ve believed about aging and retirement is wrong?

In this week’s Wisdom Wednesday, Chip and Derek dive into the surprising truth about aging. Why retirement often makes us less healthy, how community and purpose keep us alive longer, and why our “crystallized intelligence” actually gets stronger well into our 60s and 70s. They explore the real ingredients of a meaningful midlife, the magic of third-vault co...

Ever wonder if slowing down might actually wake you up? In this episode, I sit down with Susan Cain, the bestselling author of Quiet and Bittersweet, to talk about the hidden strengths of introverts, the surprising beauty in melancholy, and why midlife can be the most creative and peaceful chapter of your life. We dig into what it really means to live with depth, authenticity, and joy, without the noise.

✨ Hit play and join us for a...

What happens when two New York City professionals lose their jobs, move to a tiny rural town, and accidentally build one of America’s most beloved skincare brands?

Brent and Josh of Beekman 1802 reveal how kindness, community, and old-fashioned wisdom became the backbone of their business and their midlife reinvention. They share how loving your neighbor can be a real strategy, why contentment matters more than achievement, the 51% ...

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, clarity, and courage…

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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.

✨ Learn how to flourish, not fade, ...

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 with authenticity in midlife and be...

🔥 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 Factor documentary and her book ...

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 born to be good and how awe migh...

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 peace beyond the game.

If you’ve ev...

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 sacred turning point when the soul fin...

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 how facing mortality can open the do...

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 purpose, not paychecks.

👉 Watch now to...

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 often ignored, what every caregiver...

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 crystallized intelligence, and the simp...

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 and Super Age, two platforms ch...

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 will leave you inspired — and maybe...

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, creativity, and storytelling c...