The Midlife Chrysalis
Episodes
How an Anarchist Built One of America’s Most Unique Businesses | Ari Weinzweig
27 Mar 2026
Contributed by Lukas
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 Zin...
Men vs Women in Midlife: The Struggles No One Warns You About
25 Mar 2026
Contributed by Lukas
Most people imagine a midlife crisis as sports cars, bad decisions, and dramatic life changes. But what if midlife is actually something much deeper a...
Why Love Requires Skills Most People Never Learn
23 Mar 2026
Contributed by Lukas
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 renow...
Pete Holmes on Psychedelics, God & Finding Meaning in Midlife
20 Mar 2026
Contributed by Lukas
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 ...
Midlife Pit Stop: Refuel Before the Next Chapter
18 Mar 2026
Contributed by Lukas
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 explo...
Designing the Second Half of Life: Meaning, Curiosity, and Becoming | Bill Burnett & Dave Evans
16 Mar 2026
Contributed by Lukas
Most of us try to solve midlife. What if that’s exactly the wrong approach?In this episode, Chip Conley sits down with Bill Burnett and Dave Evans, ...
Why You Keep Repeating the Same Conflict Patterns | Diana Chapman
13 Mar 2026
Contributed by Lukas
Real growth rarely happens when life feels comfortable. It begins when we slow down, question our patterns, and face the deeper truths about how we li...
From Ego to Soul: Rewriting the Second Half of Life
11 Mar 2026
Contributed by Lukas
The drive that made you successful may not be meant to lead you forever.In this Wisdom Wednesday episode of The Midlife Chrysalis, Chip Conley and Der...
Mortality Was My Wake-Up Call | Dr. Brad Jacobs
09 Mar 2026
Contributed by Lukas
What if the real key to longevity isn’t a biohack but a wake-up call?In this episode, Dr. Brad Jacobs, longevity expert, integrative medicine pionee...
Why Midlife Feels Like Exile And Why That’s a Gift | David Whyte
06 Mar 2026
Contributed by Lukas
In this episode of Midlife Chrysalis, poet and philosopher David Whyte explores why midlife often feels like losing your way and why that experience m...
Letting Go in Midlife: What Has Run Its Course?
04 Mar 2026
Contributed by Lukas
Midlife isn’t about adding more. It’s about letting go.In this Wisdom Wednesday episode of The Midlife Chrysalis, Chip Conley joins Derek Gehl to ...
Greg Louganis: Olympic Gold, Public Masks, Private Truth
02 Mar 2026
Contributed by Lukas
What happens when the world sees a champion… but you’re still figuring out who you are?In this episode of The Midlife Chrysalis, Olympic legend Gr...
Midlife and the Moral Pressure of Limited Time | Kieran Setiya
27 Feb 2026
Contributed by Lukas
Midlife can feel unsettling even when life looks successful on paper. This episode explores why that discomfort appears and how it can become a source...
What a Cancer Diagnosis Teaches You About How to Live
25 Feb 2026
Contributed by Lukas
What happens when time stops feeling endless and starts feeling real?In this episode of Wisdom Wednesday, Chip Conley shares how living with cancer re...
From Ambition to “I’m Enough” | Brian Chesky
22 Feb 2026
Contributed by Lukas
In this candid and heartfelt conversation, Airbnb co-founder and CEO Brian Chesky joins Chip Conley to explore the hidden side of success. From impost...
Your Brain on Art: Why Midlife Needs Creativity More Than Ever | Susan Magsamen & Ivy Ross
20 Feb 2026
Contributed by Lukas
Midlife isn’t a crisis. It’s an invitation to come alive again.In this episode of Midlife Chrysalis, Chip Conley is joined by Susan Magsamen, a ne...
Why Midlife Friendships Stop Working & How to Fix Them
18 Feb 2026
Contributed by Lukas
Ever notice how some friendships don’t end, they just stop deepening?You still care about each other, but the conversations feel thinner than they u...
Why Midlife Men Struggle with Identity & Purpose Today | Greg Scheinman
16 Feb 2026
Contributed by Lukas
Ever wonder what happens when “success” still feels empty?At 47, Greg Scheinman looked like he had it all, career, family, success, yet felt compl...
Why Friendship Becomes the Most Important Skill in Midlife | Jeff Hamoui
13 Feb 2026
Contributed by Lukas
Midlife rarely falls apart all at once. It slowly grows quieter, fewer close friendships, less community, more doing and less belonging.In this episod...
What Great Mentors Do Differently in Midlife
11 Feb 2026
Contributed by Lukas
Most of us grow up thinking mentorship means having the answers. In midlife, we learn it’s really about asking better questions.In this Wisdom Wedne...
Why Wisdom Matters More Than Knowledge in Midlife | Eric Weiner
09 Feb 2026
Contributed by Lukas
We’re surrounded by information but many of us still feel unsure about how to live well. This episode gently explores why midlife pulls us toward wi...
Losing Everything to Find Purpose: Aithan Shapira’s Midlife Shift
06 Feb 2026
Contributed by Lukas
What if losing everything was the only way to truly find yourself?MIT lecturer and artist Aithan Shapira shares how the collapse of his art career bec...
Stuck at 50? How to Make a Midlife Career Change Without Starting Over
04 Feb 2026
Contributed by Lukas
What if midlife isn’t the end of your career story but the smartest place to rewrite it? In this episode of Wisdom Wednesday, Chip Conley joins Der...
How a Panic Attack Sparked a Midlife Awakening | Dan Harris
02 Feb 2026
Contributed by Lukas
He had everything going for him, until his body shut him down on live TV.In this episode, Dan Harris sits down with Chip Conley for a warm, honest con...
When Cancer Forces a Life Reset in Midlife | Caryn Lerman
30 Jan 2026
Contributed by Lukas
Cancer doesn’t just affect your health. It changes how you see yourself and your life. In this warm and honest conversation, Chip Conley sits down w...
Why Rituals Matter More Than Routines in Midlife
28 Jan 2026
Contributed by Lukas
What if the way you start your morning is quietly shaping how your whole day feels?Chip Conley sits down with Derek Gehl to explore why so many midlif...
How Ritual, Awe, and Community Bring Midlife Back to Life | Christine Sperber
26 Jan 2026
Contributed by Lukas
In this episode, Chip Conley sits down with Christine Sperber, co-founder of MEA and master experience designer, to explore how awe, ritual, and commu...
The Bonus Years: Midlife Is About Reinvention Not Retirement | Pam McLean
23 Jan 2026
Contributed by Lukas
Midlife isn’t the end of the story, it’s the chapter where something new wants to begin.In this episode of Midlife Chrysalis, Chip Conley sits dow...
Midlife Isn’t Falling Apart – It’s a Transformation
21 Jan 2026
Contributed by Lukas
Midlife isn’t falling apart. It’s asking for your attention.In this episode of Midlife Chrysalis, Chip Conley dismantles the idea of the “midlif...
Gavin Newsom on Leadership, Identity, and Becoming Yourself
19 Jan 2026
Contributed by Lukas
What happens when ambition slows down, and wisdom begins to lead? Chip Conley, founder of Modern Elder Academy and host of Midlife Chrysalis, sits dow...
He Had Everything. Midlife Broke Him Anyway | Blake Mycoskie
16 Jan 2026
Contributed by Lukas
What happens when success stops working and midlife hits hard?Blake Mycoskie, founder of TOMS Shoes, shares the story behind his most difficult chapte...
Could Golden Girls–Style Living Be the Future of Midlife Housing?
14 Jan 2026
Contributed by Lukas
What if aging alone isn’t the only option?As midlife reshapes relationships, identity, and housing, a bold question emerges: what if women chose com...
Aging While Black: Paying the Price of a Broken System | Ray Jetson
12 Jan 2026
Contributed by Lukas
Aging in America has never been the same for everyone. Chip Conley sits down with Ray Jetson, pastor, former Louisiana legislator, and author of Aging...
How Conscious Capitalism Changes the Way Leaders Think | Rand Stagen
09 Jan 2026
Contributed by Lukas
Most leaders are chasing short-term wins and missing the long game.In this episode, Chip Conley talks with Rand Stagen, founder of the Stagen Leadersh...
Why Leadership Fails When Wisdom Walks Out
07 Jan 2026
Contributed by Lukas
Most companies are racing toward AI, efficiency, and scale while quietly losing the one advantage that actually sustains great leadership: wisdom. In ...
From Breakdown to Wholeness: The Hero’s Path Through Midlife with Ben Katt
05 Jan 2026
Contributed by Lukas
Have you ever reached a point in life where what once worked… suddenly doesn’t?In this warm conversation with Chip, Ben Katt, MEA’s faculty in r...
Jeff Krasno & Schuyler Grant: What Midlife Health Really Requires
02 Jan 2026
Contributed by Lukas
What if the wellness advice you followed for years stops working after 50?In this episode, wellness pioneers Jeff Krasno, co-founder of Wanderlust, an...
Stop Starting Over: How to Build Habits That Actually Last
31 Dec 2025
Contributed by Lukas
Why most New Year’s resolutions fail before February? In this episode of Wisdom Wednesday, we take an honest look at why good intentions fade quickl...
Why Transitions Break Us and Heal Us | Kari Cardinale
29 Dec 2025
Contributed by Lukas
Midlife can feel confusing, even when life looks good from the outside. Careers change, relationships shift, and the way we see ourselves starts to ev...
From Skateboarding Icon to Modern Elder: Stacy Peralta
26 Dec 2025
Contributed by Lukas
He didn’t plan on being successful. He just followed what pulled at him and kept letting go when it stopped working. In this episode, Stacy Peralta,...
The Success Treadmill Is Real: Here’s How to Escape
24 Dec 2025
Contributed by Lukas
In this Wisdom Wednesday episode, Chip Conley, entrepreneur, author, and founder of MEA, opens up about the quiet disappointment many high achievers f...
The Hidden Cost of Playing It Safe in Midlife | Dr. Margie Warrell
22 Dec 2025
Contributed by Lukas
What if the real risk in midlife isn’t change but staying comfortable?In this episode of Midlife Chrysalis, Chip Conley sits down with Dr. Margie Wa...
Why Dating Feels Hard in Midlife (Even for Smart People) | Rachel Greenwald
19 Dec 2025
Contributed by Lukas
Dating in midlife can feel strangely hard, even when you’ve done the work, built a full life, and know yourself better than ever. If you’ve ever t...
Inside the Messy Middle: What Actually Drives Transformation in Midlife
17 Dec 2025
Contributed by Lukas
Feeling stuck in midlife? You might be in your chrysalis, not a crisis.In this Wisdom Wednesday episode, Chip Conley breaks down why midlife often fee...
Michael Clinton on Life Layering: How to Build a Richer Life After 50
15 Dec 2025
Contributed by Lukas
What if midlife became your chance to ROAR, not retire?In this powerful conversation, bestselling author and longevity visionary Michael Clinton share...
Laird Hamilton & Gabby Reece on Love, Longevity, and Aging with Power
12 Dec 2025
Contributed by Lukas
Ever wondered why some people get stronger, wiser, and more grounded with age?In this powerful conversation, Laird Hamilton and Gabby Reece reveal why...
How Curiosity Fuels a Longer, Healthier Life
10 Dec 2025
Contributed by Lukas
What if the secret to living longer isn’t in your genes… but in your mindset?In this Wisdom Wednesday episode, Chip Conley reveals the surprising ...
Marianne Williamson: The Courage to Age, Evolve & Challenge Power
08 Dec 2025
Contributed by Lukas
What if everything you’ve believed about midlife is completely outdated?In this powerful conversation, Marianne Williamson sheds light on the truth ...
Dan Buettner on Aging Smarter: The Real Secrets of Longevity
05 Dec 2025
Contributed by Lukas
What if living to 100 is more realistic than you think?Longevity expert Dan Buettner breaks down the real habits behind the world’s longest-living p...
Growing Whole: Why Midlife May Be the Best Time of Your Life
03 Dec 2025
Contributed by Lukas
What if midlife is actually the start of your happiest years?In this episode, Chip Conley and Derek Gall break down why life often gets better after 5...
Don Lemon: Breaking Free, Speaking Truth, and Owning Midlife
01 Dec 2025
Contributed by Lukas
What happens when Don Lemon gets truly unfiltered?In this heartfelt, funny, and deeply honest conversation, Don opens up about aging with confidence, ...
Meghan Jarvis on Grief, Growth, and Finding Purpose in Midlife
28 Nov 2025
Contributed by Lukas
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 mento...
Why Retirement Is Failing Us And What to Do Instead
26 Nov 2025
Contributed by Lukas
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 tr...
Why Introverts Hold Hidden Strength | Susan Cain on Quiet Power
24 Nov 2025
Contributed by Lukas
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, ...
From Goat Farm to Global Brand: Midlife Lessons with Brent & Josh
21 Nov 2025
Contributed by Lukas
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 s...
From Experience to Wisdom: A Midlife Conversation That Matters
19 Nov 2025
Contributed by Lukas
In the very first episode of Wisdom Wednesdays, Chip Conley and Derek Gehl sit down for a thoughtful, honest conversation about what wisdom really mea...
Barbara Waxman: How to Flourish and Find Purpose in Midlife
17 Nov 2025
Contributed by Lukas
Midlife isn’t a crisis. It’s your greatest awakening.In this inspiring episode, gerontologist and coach Barbara Waxman redefines aging through the...
Mark Nepo: How to Stay Creative, Awake, and Fully Alive in Midlife
14 Nov 2025
Contributed by Lukas
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...
From Hot Flashes to a Global Mission: Tamsen Fadal’s Menopause Journey
10 Nov 2025
Contributed by Lukas
🔥 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...
The Science of Awe: Rediscover Wonder with Dacher Keltner
07 Nov 2025
Contributed by Lukas
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, ...
Reborn at Midlife: How Ricky Williams Became Errick Miron
03 Nov 2025
Contributed by Lukas
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 powerf...
Rainn Wilson: Finding the Soul Beyond the Spotlight
31 Oct 2025
Contributed by Lukas
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 conversati...
BJ Miller: How Facing Death Taught Me to Live More Fully
27 Oct 2025
Contributed by Lukas
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—physici...
Daniel Pink: The Power of Regret and the Freedom to Begin Again
22 Oct 2025
Contributed by Lukas
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 ...
Love, Loss & Caregiving with Bruce Willis’ Wife, Emma Heming Willis
15 Oct 2025
Contributed by Lukas
What happens when the person you love most slowly begins to disappear before your eyes? In this deeply emotional and inspiring conversation, Emma Hemi...
Arthur Brooks on How to Break Free from the Striver’s Curse in Midlife
08 Oct 2025
Contributed by Lukas
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...
From Near Death to Super Age: David Stewart’s Bold Reboot
01 Oct 2025
Contributed by Lukas
What happens when a world-famous photographer nearly loses everything — and turns it into a movement redefining aging?In this powerful conversation,...
Midlife Awakening & Spiritual Growth with Anne Lamott & Neal Allen
24 Sep 2025
Contributed by Lukas
What happens when a bestselling writer and a former corporate executive dive deep into life’s second half?In this powerful conversation, Anne Lamott...
How to Rewrite Your Story After a Life Quake with Bruce Feiler
17 Sep 2025
Contributed by Lukas
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 ...
Elizabeth Gilbert’s Untold Story of Love and Addiction
10 Sep 2025
Contributed by Lukas
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 joi...
From Punk Rock Pastor to Spiritual Outlaw: Rob Bell’s Midlife Reinvention
03 Sep 2025
Contributed by Lukas
What happens when one of America’s most celebrated pastors dares to question everything?In this unfiltered conversation, Rob Bell, once dubbed the “...
How Intergenerational Living Creates Purpose & Joy | Marc Freedman
27 Aug 2025
Contributed by Lukas
What if aging wasn’t about slowing down—but about leveling up?In this powerful conversation, Marc Freedman, founder of Encore.org (now CoGenerate)...
Aging Boldly and Living on Your Own Terms with Karen Walrond
20 Aug 2025
Contributed by Lukas
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 t...
Martha Beck on Psychic Gifts, Polyamory, and Finding Purpose
13 Aug 2025
Contributed by Lukas
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 th...
How Sara Blakely Built Spanx and Found Her Next Big Purpose
06 Aug 2025
Contributed by Lukas
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, t...
What 50 Years with the Dalai Lama Taught About Midlife | Pico Iyer
30 Jul 2025
Contributed by Lukas
What if midlife isn’t a breakdown—but a breakthrough?In this powerful conversation, world-renowned writer Pico Iyer shares the surprising lessons ...
From Famous Father to Finding Purpose: Scott Eastwood at Midlife
23 Jul 2025
Contributed by Lukas
What happens when a successful actor—and the son of a Hollywood legend—hits midlife and starts asking deeper questions?In this powerful episode, S...
Why Krista Tippett Walked Away at the Peak of Her Career
16 Jul 2025
Contributed by Lukas
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 bur...
What Burning Man Teaches Us About Aging, Identity & Legacy | Marian Goodell
10 Jul 2025
Contributed by Lukas
What if your so-called “midlife crisis” was actually a doorway to reinvention? In this powerful conversation, Burning Man CEO Marian Goodell joins...
Psychedelics, Purpose & the Next Chapter of John Mackey’s Life
02 Jul 2025
Contributed by Lukas
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 res...
Rich Roll on Reinventing Yourself After Rock Bottom
25 Jun 2025
Contributed by Lukas
What if hitting rock bottom was the best thing that ever happened to you?In this raw and inspiring conversation, Rich Roll, a former addict turned wor...
Reinvention After 50 with Seth Godin: Make Life Your Best Work of Art
18 Jun 2025
Contributed by Lukas
What if midlife isn’t a crisis, but your most creative chapter yet?In this inspiring and deeply personal episode, bestselling author and entrepreneu...
You Can’t Scare Me: Hoda Kotb on Starting Over and Fearless Living After 50
11 Jun 2025
Contributed by Lukas
At 40, Hoda Kotb’s world fell apart—cancer, divorce, and the dream of having children slipping away. But what came next wasn’t the end. It was a...
From Wall Street to Inner Peace: The Emotional Journey of Jerry Colonna
02 Jun 2025
Contributed by Lukas
What if the life you built is no longer the one that fulfills you? In this powerful episode, former venture capitalist turned CEO coach Jerry Colonna ...
Break Up With What You Don’t Need: Michael Franti on Healing & Growth
02 Jun 2025
Contributed by Lukas
What if midlife isn’t a crisis—but a chance to grow, heal, and start fresh? In this episode, Michael Franti shares how he transformed personal pai...
Maria Shriver: Healing Old Wounds & Becoming Who You Were Meant to Be
02 Jun 2025
Contributed by Lukas
What if the most powerful transformation of your life came after the titles, the heartbreak, and the noise? In this deeply moving episode, Maria Shriv...
Intro
02 Jun 2025
Contributed by Lukas
Welcome to the very first episode of The Midlife Chrysalis!Chip Conley kicks off this amazing podcast by redefining midlife. It’s not as a crisis, b...