The Midlife Chrysalis

Have you ever wondered what your 80 year old self would tell you today?

In this episode, Derek and Chip talk about aging, relationships, purpose, and the life lessons that only become clear with time. Through a powerful exercise imagining a conversation with his future self, Chip shares the insights that have reshaped how he thinks about success, love, health, and what truly matters.

In this episode, you'll discover:
Why talking to your future self can help you make better decisions today.
The surprising relationship lesson that completely changed Chip's perspective on growing older.
How a simple journaling exercise unlocked unexpected insights and self reflection.
Why success, legacy, and achievement become less important than the people you grow with.
How your priorities naturally evolve as you move through the second half of life.

If you're navigating midlife, rethinking your priorities, or simply looking for a fresh perspective on what makes a meaningful life, this conversation is full of wisdom you won't want to miss.

🎧 Watch the full episode and join the conversation.

Timestamps:
(00:00) Welcome
(01:53) Talking to Your Elder Self
(04:17) Lessons From Your Future Self
(06:43) The Importance of Relationships
(10:44) Leaving a Meaningful Legacy
(11:44) Taking Better Care of Your Health
(12:43) How to Do the Elder Self Exercise
(15:33) What the Experience Felt Like
(18:06) Applying the Lessons to Life
(20:09) Building a Lasting Legacy
(21:28) Final Thoughts

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#FutureSelf #FutureSelfExercise #ChipConley #MidlifeChrysalis #MidlifeWisdom #GrowingOlder #LifeLessons #MeaningfulRelationships #PersonalLegacy #SelfReflection #Journaling #Purpose #HealthyAging #PersonalGrowth #SecondHalfOfLife

Burnout, career uncertainty, and midlife stuckness have become increasingly common, but stepping away may be the key to moving forward.

In this episode, Chip Conley sits down with DJ DiDonna, Harvard Business School senior lecturer, entrepreneur, and author of Big Time Off. After reaching burnout while running his dream company, DJ took a four-month sabbatical that transformed his perspective on work, success, and life.

In this conversation, DJ shares:
Why burnout is often a sign that something needs to change
How sabbaticals create space for clarity, growth, and reinvention
The role of travel, pilgrimage, and reflection in personal transformation
Why midlife is the perfect time to reassess your priorities
Practical advice for planning a sabbatical, even if it feels out of reach

If you're feeling stuck, overwhelmed, or ready for a new chapter, this conversation offers a powerful reminder that sometimes the most important step forward is taking a step back.

Listen now and discover the transformative power of time away.

Timestamps:
(01:47) Introduction & DJ’s New Book
(02:53) Burnout That Led to a Sabbatical
(04:42) The Freedom of Having No Structure
(06:18) Why Pilgrimages Transform People
(10:47) What Changed After Four Months Away
(13:08) Sabbaticals Inside Organizations
(16:20) Do Employees Leave After Sabbaticals?
(20:40) How Sabbaticals Improve Retention
(22:20) The Value of Floating Managers
(24:20) Fear, Burnout & Quiet Quitting
(25:51) Why Midlife Needs Sabbaticals
(31:00) Creating Midlife Inflection Points
(32:20) The Three Sabbatical Archetypes
(35:30) How to Take a Successful Sabbatical
(39:40) Planning for Sabbaticals Financially
(41:10) Sabbaticals as Regret Insurance
(42:40) Wisdom Bumper Sticker

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#Sabbatical #MidlifeReset #PersonalGrowth #CareerChange #BurnoutRecovery #Midlife #LifeTransition #SelfDiscovery #WorkLifeBalance #PurposeDrivenLife #PersonalDevelopment #CareerReinvention #TimeOff #ChipConley #MidlifeChrysalis

Can your greatest purpose begin after 50?

In this powerful conversation, Chip Conley sits down with Lynne Twist, bestselling author of The Soul of Money, and her longtime collaborator Sara Vetter to explore purpose, money, mentorship, and the surprising opportunities that come with midlife.

In this episode, you'll learn:
Why midlife can be the start of your most meaningful chapter.
How a life-changing trip to the Amazon transformed their paths.
The mindset shift that can completely change your relationship with money.
Why great partnerships are built on trust, honesty, and shared purpose.
How joy and gratitude can shape a richer, more fulfilling life.

Enjoyed this conversation? Like, subscribe, and share it with a friend.
Then tell us in the comments: Has midlife changed your perspective on purpose, money, or what truly matters?

Timestamps:
(05:12) How Lynn and Sara Became Partners
(12:02) Sara's Life-Changing Experience at 50
(15:02) The Secret to a Lasting Partnership
(18:08) Navigating Conflict with Honesty
(20:45) Why the Pachamama Alliance Matters
(27:11) Ayahuasca, Healing, and the Amazon
(31:52) Why Midlife Can Change Your Life
(37:52) Lynn's Calling at Age 50
(43:45) The Soul of Money Explained
(48:07) How to Transform Your Money Mindset
(53:16) Life Lessons to Live By

Learn more about MEA at ⁠https://www.meawisdom.com/

#LynneTwist #SaraVetter #ChipConley #Midlife #Purpose #TheSoulOfMoney #MoneyMindset #PersonalGrowth #LifeAfter50 #MeaningfulLife #MidlifeTransformation #SelfDiscovery #ConsciousLiving #AgingWell #PachamamaAlliance

Uncertainty is everywhere, from economic shifts and AI disruption to health challenges and major life transitions. The question isn't how to eliminate uncertainty, but how to navigate it with confidence.

In this Wisdom Wednesday episode, Chip Conley and Derek Gehl explore practical ways to stay grounded when life feels unpredictable. Drawing from his experiences as an entrepreneur and his ongoing cancer journey, Chip shares the tools that have helped him face uncertainty with greater resilience, clarity, and purpose.

In this episode, you'll learn:
Why uncertainty is a normal part of life
The connection between anxiety, uncertainty, and powerlessness
How to focus on what you can control
Why intuition and wisdom matter most during difficult times
A simple exercise for reducing stress and making better decisions

Listen now, and if you enjoy the episode, be sure to subscribe, leave a review, and share it with a friend.

Timestamps:
(00:00) Introduction
(01:28) How to Navigate Uncertainty
(04:14) Reducing Uncertainty Through Questions
(06:42) Powerlessness and Agency
(09:24) Lessons from Business Crises
(11:18) Cancer, Denial, and Taking Action
(13:22) Living in the Present Moment
(14:32) Letting Go of Control
(17:41) Key Lessons About Uncertainty
(19:33) The Serenity Prayer and Wisdom
(20:27) Building Confidence in Decisions
(21:40) The Anxiety Balance Sheet Exercise
(23:10) Worst Case vs Best Case Thinking
(24:02) Final Thoughts

Learn more about MEA at ⁠https://www.meawisdom.com/

#Uncertainty #Anxiety #MentalHealth #PersonalGrowth #WisdomWednesday #ChipConley #Resilience #SelfImprovement #LifeLessons #Mindset #EmotionalIntelligence #DecisionMaking #StressManagement #PersonalDevelopment #Midlife

AI is changing the way we work, but the skills that matter most are still deeply human.

In this episode of The Midlife Chrysalis, Chip Conley is joined by Chris Shipley, technology visionary and leadership expert, and Scott Barry Kaufman, psychologist and bestselling author, for a thoughtful conversation about leadership, purpose, and human potential in the age of AI.

Together, they explore why the future belongs to leaders who combine technology with wisdom, curiosity, and genuine human connection.

In this episode, you'll discover:
Why human skills will become even more valuable as AI evolves
How leaders can reduce fear and build trust during times of change
Why wisdom may be your greatest advantage in the future
How different generations can learn from each other
Why having a clear vision for your future self can change your life

Whether you're leading a team, planning your next career move, or simply wondering what the future of work will look like, this conversation offers practical ideas and a hopeful perspective.

Watch now and discover why the future belongs to leaders who never stop growing.

Timestamps:
(00:00) Intro
(00:42) Introducing Chris Shipley & Scott Barry Kaufman
(02:07) Leading For Tomorrow
(05:53) The Future Of Human-Centered Leadership
(07:11) What Would Maslow Think About AI?
(08:56) Leading Through AI Uncertainty
(11:24) Easing AI Anxiety At Work
(14:13) What Makes People Feel They Matter
(16:50) Best Lessons From The Book
(22:39) Midlife In Silicon Valley
(26:52) Becoming An Integrator In Midlife
(28:33) Bridging The Generational Gap
(35:10) Wisdom For Your Younger Self
(39:27) Three Key Takeaways

Learn more about MEA at ⁠https://www.meawisdom.com/

#AILeadership #HumanLeadership #FutureOfLeadership #FutureOfWork #LeadershipSkills #HumanPotential #ScottBarryKaufman #ChrisShipley #ChipConley #AIAnxiety #LeadershipDevelopment #HumanCenteredLeadership #Wisdom #EmotionalIntelligence #MidlifeChrysalis