The Midlife Chrysalis

Why Success Alone Will Never Fulfill You | Brad Stulberg

22 May 2026

Contributed by Lukas

You hit your biggest goals… and still feel empty?In this episode, performance expert and bestselling author Brad Stulberg breaks down why success al...

Why So Many Successful People Struggle With Retirement

20 May 2026

Contributed by Lukas

Why So Many Successful People Struggle With Retirement What Comes After Ambition but Before Retirement?The Hidden Midlife Crisis Between Success and R...

Why Modern Life Is Terrified Of Death | Ben Yalom

18 May 2026

Contributed by Lukas

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 for...

Why Facing Mortality Changes How You Live | Dr. Kerry Burnight

15 May 2026

Contributed by Lukas

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 sh...

What Keeps You Together When Everything Falls Apart?

13 May 2026

Contributed by Lukas

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 s...

Feeling Stuck at 50: How to Find Your Magic and Start Again | Matt Ross

11 May 2026

Contributed by Lukas

The moment everything starts falling apart might be the moment your life finally comes together.In this episode, Chip Conley sits down with entreprene...

What Horses, Death, and Nature Taught Me About Being Human | Kelly Wendorf

08 May 2026

Contributed by Lukas

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, ...

AI vs Humans: The One Skill AI Still Can’t Replace

06 May 2026

Contributed by Lukas

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 d...

The New Way Women Over 50 Are Choosing to Live | Elizabeth White

04 May 2026

Contributed by Lukas

In this powerful conversation, Elizabeth White, author of 55, Underemployed, and Faking Normal, shares how losing everything during the recession led ...

You Were Never Meant to Think This Way | Angus Fletcher

01 May 2026

Contributed by Lukas

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 li...

Why Success Stops Making You Happy After 40

29 Apr 2026

Contributed by Lukas

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...

You Did Everything Right… So Why Does It Feel Wrong? | Jill Nykoliation

27 Apr 2026

Contributed by Lukas

You can have a career, success, and still feel like something is missing.In this episode, Jill Nykoliation, former CEO of a globally recognized brandi...

The Real Reason You’re Aging Faster Than You Should | Dr. Florence Comite

24 Apr 2026

Contributed by Lukas

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 physi...

Take a Month Off and See Who You Become

22 Apr 2026

Contributed by Lukas

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 f...

How to Heal Trauma in Your Body and Mind | Rebecca & Jaimie

20 Apr 2026

Contributed by Lukas

In this powerful episode of the Midlife Chrysalis, Chip Conley sits down with two women who’ve pushed their limits, physically, emotionally, and psy...

Stop Living on Autopilot. Start Living for Real | Bonnie Wan

17 Apr 2026

Contributed by Lukas

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 ren...

Knowledge Won’t Save You. Curiosity Will

15 Apr 2026

Contributed by Lukas

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 b...

She Quit a 30-Year Career to Help Others Rebrand Their Lives | Robin Fisher Roffer

13 Apr 2026

Contributed by Lukas

Midlife might be the moment everything finally starts to make sense.In this episode of The Midlife Chrysalis, Chip sits down with branding expert Robi...

Feeling Lost? Use Inner Tracking to Find Your Path| Lee Johnson

10 Apr 2026

Contributed by Lukas

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 John...

Stuck Between Aging Parents and Grown Kids in Midlife?

08 Apr 2026

Contributed by Lukas

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 ...

Leading in Chaos: How to Stay Grounded Under Pressure | Amy Elizabeth Fox

06 Apr 2026

Contributed by Lukas

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 Mo...

She Told 80,000 Employees the Truth She Hid Her Entire Life | Katherine Dudtschak

03 Apr 2026

Contributed by Lukas

She had the perfect life - career, family, success - and a secret she kept hidden for decades.In this episode, Katherine Dudtschak, a former top banki...

Why So Many Men Lose Friends in Midlife (And How to Fix It)

01 Apr 2026

Contributed by Lukas

What if the biggest factor for a longer, happier life isn’t health, but friendship?In this Wisdom Wednesday episode, Chip Conley joins Derek Gehl to...

Death, Belonging, and What It Means to Be Human | Sebastian Junger

30 Mar 2026

Contributed by Lukas

He was bleeding out… and didn’t even know he was dying.In this powerful conversation, war journalist and bestselling author Sebastian Junger share...

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 ...