The Midlife Chrysalis

Chip Conley
  • 4.9 (82)
  • Self-Improvement
  • Weekly

The Midlife Chrysalis is a one-hour podcast hosted by Chip Conley, bestselling author of Learning to Love Midlife and founder of MEA (Modern Elder Academy). Chip and his high-profile guests – including Maria Shriver, Hoda Kotb, Elizabeth Gilbert, Michael Franti, and more – dive into raw, vulnerable conversations about the profound transitions they’ve experienced in midlife. Listeners get a rare look at how even the most successful individuals have to navigate life’s pivotal changes – and gain practical wisdom they can apply in their own lives for a more fulfilling and purposeful next chapter.

  1. 1d ago

    Yung Pueblo: Wisdom Begins When You Stop Fighting Change

    Getting older doesn’t automatically make you wiser. How you meet change matters more. In this episode of The Midlife Chrysalis, bestselling author Diego Perez, known as Yung Pueblo, joins Chip Conley to explore how we cultivate wisdom at any age. From growing up in poverty to hitting rock bottom at 23, Diego shares how meditation changed his relationship with himself and the world. Drawing on those experiences and his new book, Journey, he explores: Why inner peace takes more than getting your circumstances rightHow fighting change creates stress and keeps us stuckWhat silence can teach us about our emotions and patternsHow accepting impermanence helps us appreciate the people we loveWhy personal growth takes practice, patience, and time Watch the full episode for a thoughtful conversation about growing wiser, finding peace, and meeting life with greater openness. Timestamps: (00:00) Introduction (03:16) Cultivating Wisdom Through Meditation (04:36) Growing Up in Poverty (06:26) Activism, Addiction, and Hitting Rock Bottom (10:30) Finding Creativity in Silence (12:58) Why Wisdom Is More Than Age (15:13) Presence, Ego, and Time (17:12) Bringing Meditation Into Daily Life (18:04) Love Beyond a Feeling (22:00) Making Peace With Impermanence (23:56) Becoming Yung Pueblo (26:30) How His Writing Found an Audience (28:00) Journey and the Work of Personal Growth (29:52) Cultivating Inner Peace (31:56) How Technology Pulls Us From the Present (33:01) Finding Hope in Today’s World (37:22) Finding a Meditation Practice That Fits (38:46) Embracing Change and Letting Go of Labels Learn more about MEA at ⁠https://www.meawisdom.com/ #YungPueblo #DiegoPerez #MidlifeChrysalis #ChipConley #Wisdom #MidlifeWisdom #EmbracingChange #InnerPeace #Meditation #Mindfulness #PersonalGrowth #LettingGo #SelfAwareness #Impermanence #Journey

  2. 3d ago

    Better Questions, Better Hires: Chip Conley’s Top 10

    You hired the perfect candidate. Then you met the real person. A great interview performance doesn’t always mean a great hire. In this Wisdom Wednesday episode, MEA founder Chip Conley joins Derek Gehl to share 10 favorite interview questions from 40 years of hiring. These questions get past polished answers to reveal how someone thinks, learns, and treats others. Discover: The unexpected question that reveals how people see themselves.Why a failure can tell you more than a success.What someone’s reaction to setbacks reveals about their character.How to challenge candidates without making them feel ambushed.Simple questions that turn everyday small talk into meaningful conversations. Watch the full episode and borrow a question that could Timestamps: (00:00) Introduction (00:55) Better Interview Questions (02:55) Self-Awareness (05:32) Learning from Failure (07:20) Leadership Philosophy (09:54) Bringing Out the Best (10:13) Handling Setbacks (10:58) Open Mindedness (12:21) Challenging Popular Beliefs (13:48) Asking with Empathy (16:06) Appreciative Inquiry (17:46) Better Everyday Questions (18:31) Avoiding Future Regret Learn more about MEA at ⁠https://www.meawisdom.com/ #ChipConley #MidlifeChrysalis #WisdomWednesday #InterviewQuestions #Hiring #Leadership #EmotionalIntelligence #SelfAwareness #GrowthMindset #AppreciativeInquiry #LeadershipWisdom #HiringTips #InterviewTips #BetterQuestions #MeaningfulConversations

  3. 5d ago

    The Kids Have Left. Who Are You Now? | Gretchen Rubin

    When a role has shaped your life for years, stepping back from it can leave you wondering who you are without it. In this episode of The Midlife Chrysalis, bestselling author Gretchen Rubin joins Chip Conley to explore happiness, identity, and finding yourself again after a big transition like the empty nest. Gretchen shares: Three ways to rebuild your identity as your role changesA simple exercise to reconnect with what you actually likeWhy happiness advice needs to fit youHow to decide when to accept yourself and when to push through discomfort Watch the full episode for practical ways to rediscover what matters to you and choose what comes next. Timestamps: (01:33) Meet Gretchen Rubin (02:04) Connecting with Your Five Senses (04:48) Learning to Be Present (09:02) Why Happiness Looks Different for Everyone (12:10) Finding Your Happiness Habits (13:24) Making Time for Everyday Joy (16:19) Why Mishaps Make the Best Memories (17:50) The Secrets of Adulthood (23:22) Navigating the Empty Nest (25:45) Relationships After Children Leave (28:43) Rediscovering Your Identity (32:18) How Others Misperceive Us (35:13) Understanding the Four Tendencies (37:22) Accepting Yourself and Expecting More (39:41) When to Push Beyond Your Comfort Zone (41:25) What Will You Regret Not Doing? Learn more about MEA at ⁠https://www.meawisdom.com/ #GretchenRubin #ChipConley #TheMidlifeChrysalis #Happiness #EmptyNest #Midlife #PersonalGrowth #SelfDiscovery #HealthyHabits #LifeInFiveSenses #TheFourTendencies #TheHappinessProject #SelfAcceptance #SecretsOfAdulthood #Identity

  4. Nov 6

    Your Turn: How to Create a Midlife You Love with Allison Aubrey

    You’ve spent years building a career, caring for others, and doing what’s expected. Midlife is your chance to ask: Who am I now, and what do I want next? NPR health and science journalist Allison Aubrey joins Chip Conley to explore how to create a midlife you love. Drawing on her book, Your Turn, she shares practical ways to find more joy, care for your health, and decide what comes next. You’ll learn: How to reinvent yourself without starting overWhy slowing down helps you hear what you really wantHow to rethink retirement around what you enjoyHow the Brain Care Score can guide healthier habitsWhy finding purpose doesn’t require a big life change Watch the full conversation for a fresh look at midlife and the possibilities ahead. Timestamps: (06:44) Meet Allison Aubrey (08:30) Food as Medicine (09:36) The Value of Midlife Wisdom (11:19) Creating a Midlife You Love (14:04) The Kentucky Derby Midlife Metaphor (19:07) Reinventing Yourself Through Play (24:34) Finding the Courage to Change (26:47) Allison’s Career Transition (30:00) Menopause and Changing Priorities (33:15) Rethinking Retirement (37:36) The Brain Care Score (42:46) Finding Purpose in Everyday Life (47:37) Rediscovering Your Joyful Self Learn more about MEA at ⁠https://www.meawisdom.com/ #Midlife #AllisonAubrey #ChipConley #YourTurn #MidlifeChrysalis #MidlifeReinvention #LifeAfter50 #HealthyAging #FindingPurpose #SelfDiscovery #BrainHealth #Menopause #RethinkingRetirement #PersonalGrowth #MidlifeTransitions

  5. Nov 4

    AI Can Save You Time. Is It Costing You Your Creativity?

    AI can save you hours. But are you handing over more than your workload? In this Wisdom Wednesday episode of the Midlife Chrysalis podcast, Chip Conley and Derek Gehl explore how to use AI without losing your voice, creativity, or judgment. Together, they discuss: How they use AI to save time on research and everyday workWhy polished writing can lose the personality that makes it yoursHow outsourcing your thinking can mean missing opportunities to learnWhat makes your skills and experience valuable in the AI eraA simple experiment to decide which tasks to keep doing yourself Watch the full episode to discover where AI can help and where your human experience matters most. Timestamps: (00:00) Introduction (01:12) Will AI Change Everything? (04:19) Use AI Without Letting It Think for You (06:28) How Chip Uses AI to Save Time (10:24) Is AI Making Us Less Creative? (12:43) Why Human Content Still Matters (14:19) What AI Misses About Human Wisdom (16:01) Finding Your Place in an AI World (19:44) Why Human Connection Will Matter More (20:49) What You Should Never Outsource to AI Learn more about MEA at ⁠https://www.meawisdom.com/ #AI #ArtificialIntelligence #HumanConnection #FutureOfWork #CriticalThinking #HumanCreativity #AIProductivity #Midlife #ChipConley #WisdomWednesday #HumanWisdom #Authenticity #CareerReinvention #LifelongLearning #MidlifeChrysalis

  6. Nov 2

    You Have a Book in You. Here’s How to Finally Write It | Kelly Notaras

    That book you’ve been meaning to write isn’t going to write itself. And according to publishing expert Kelly Notaras, you don’t need a perfect plan, a polished first chapter, or even a publisher to get started. Kelly, founder of KN Literary Arts and author of The Book You Were Born to Write, has helped nearly 3,000 authors bring their ideas to the page. In this conversation, she shares what decades in publishing have taught her about writing, creativity, and getting a book into the world. In this episode, Kelly shares: Why midlife can be a powerful time to finally write the book you’ve been carryingThe three things publishers are looking for from authors todayWhy self publishing is no longer Plan B and can actually open doors to traditional publishingHow perfectionism keeps writers stuck and why the first draft needs to be messyWhy finding the right time, space, and people to write with can transform your creative process If there’s a book you keep telling yourself you’ll write someday, this conversation is a great place to start. Watch the full episode and discover how to stop waiting and start writing. Timestamps: (03:54) Kelly’s Journey Into Publishing (06:45) Leaving Traditional Publishing (10:42) Working With 3,000 Authors (13:44) What Publishers Look for Today (19:31) Traditional vs. Self-Publishing (23:25) The Best Way to Self-Publish (24:34) Why Midlife Is the Perfect Time to Write (29:00) How to Create Your Best Writing (32:30) Inside a Writing Retreat (36:08) Turning Life Experience Into a Book (39:11) The Most Important Lesson Kelly Learned (39:49) Don’t Just Do Something, Sit There Learn more about MEA at ⁠https://www.meawisdom.com/ #WritingABook #MidlifeWriting #BookWriting #WritingTips #AspiringAuthors #SelfPublishing #PublishingTips #CreativeWriting #WritingInMidlife #BookPublishing #KellyNotaras #KNLiteraryArts #MidlifeCreativity #FirstDraft #MidlifeChrysalis

  7. Oct 30

    Stop Chasing Happiness: Find Joy in the Life You Have | Mark Coleman & Lori Schwanbeck

    You can spend years chasing happiness and miss the life happening right in front of you. In this episode of The Midlife Chrysalis, Chip Conley joins mindfulness teachers Mark Coleman and Lori Schwanbeck to explore how to feel more present, connected, and fully alive in midlife. Together, they explore: How changing what you pay attention to can change your experience of lifeWhy nature makes mindfulness easier and teaches us to let goHow gratitude helps you appreciate your life, even when things are hardWhy midlife’s losses and transitions can open the door to new possibilitiesHow to quiet your inner critic and recognize your own worth Watch the full episode for simple ways to step out of your head, reconnect with the world around you, and find more joy in the life you have. Timestamps: (06:27) Meet Mark and Lori (07:23) Lori’s Path to Mindfulness (10:34) From Punk Rock to Meditation (13:03) Finding Peace in the Present (15:42) How to Reframe Your Thoughts (17:40) Mindfulness in a Distracted World (19:53) Why Nature Helps Us Slow Down (23:36) Making Meditation Easier Outdoors (26:10) Why Midlife Sparks Inner Change (29:53) Facing Mortality and Loss (33:51) Psychedelics and New Possibilities (37:13) Gratitude and Nature in Baja (39:43) Making Gratitude a Daily Practice (41:34) Gratitude Versus Gratification (43:06) Remembering to Fully Live (45:27) Making Peace with Your Inner Critic Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeChrysalis #ChipConley #MarkColeman #LoriSchwanbeck #Mindfulness #Midlife #MidlifeTransition #NatureMeditation #Gratitude #MindfulLiving #LettingGo #SelfCompassion #InnerCritic #PersonalGrowth #FindingJoy

  8. Oct 28

    Dreading the Holidays? Create Traditions You Actually Enjoy

    The kids have moved out. Family gatherings feel complicated. Suddenly, the holidays you used to love leave you wondering where you belong. In this Wisdom Wednesday episode, MEA founder Chip Conley joins host Derek Gehl to explore why holidays change in midlife and how new traditions can bring back a sense of connection. Discover how to: Build celebrations around people you genuinely want to spend time with.Embrace Friendsgiving without the guilt of breaking with tradition.Find friendship and a fresh start through a holiday retreat.Plan a meaningful gathering without taking on all the work. Watch now for inspiration to make this holiday season feel more connected, more joyful, and more your own. Timestamps: (00:00) Introduction (01:44) How Holidays Change in Midlife (02:14) Loneliness and Chosen Family (06:14) Choosing Friendsgiving Over Family Drama (07:20) Creating a New Year’s Tradition (08:46) Holiday Retreats in Santa Fe and Baja (11:05) Finding Connection During the Holidays (12:03) Choosing Your Friendsgiving Guests (12:41) Planning Ahead for the Holidays (14:25) Making Holiday Gatherings Easier (15:30) Upcoming Thanksgiving Workshops Learn more about MEA at ⁠https://www.meawisdom.com/ #Midlife #Holidays #Friendsgiving #ChosenFamily #HolidayLoneliness #NewTraditions #ChipConley #MidlifeChrysalis #HolidayStress #Connection #Thanksgiving #FamilyDynamics #HolidayRetreats #MeaningfulHolidays #MEA

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4.9
out of 5
82 Ratings

About

The Midlife Chrysalis is a one-hour podcast hosted by Chip Conley, bestselling author of Learning to Love Midlife and founder of MEA (Modern Elder Academy). Chip and his high-profile guests – including Maria Shriver, Hoda Kotb, Elizabeth Gilbert, Michael Franti, and more – dive into raw, vulnerable conversations about the profound transitions they’ve experienced in midlife. Listeners get a rare look at how even the most successful individuals have to navigate life’s pivotal changes – and gain practical wisdom they can apply in their own lives for a more fulfilling and purposeful next chapter.

Information

  • Creator
    Chip Conley
  • Years Active
    2025 - 2026
  • Episodes
    186
  • Rating
    Explicit
  • Copyright
    © Chip Conley
  • Show Website
    The Midlife Chrysalis

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