The Midlife Chrysalis

What happens when you achieve the success you've worked for... and it still doesn't feel like enough?

In this episode of The Midlife Chrysalis, Chip Conley sits down with executive coach and Velocity Coaching founder Edward Sullivan to explore one of the most overlooked challenges of midlife: figuring out what comes after success.

Drawing on years of coaching founders, CEOs, and high achievers, Edward shares why so many people feel restless after reaching major goals, how AI is reshaping work and leadership, and what it really takes to build a meaningful life in the second half of adulthood.

Key insights include:
Why success often creates unexpected emptiness
How AI is changing leadership and work
The role curiosity plays in personal growth
Why self-care is a leadership skill
A powerful question that can help shape your next decade

If you're navigating midlife, rethinking your priorities, or wondering what comes after achievement, this conversation offers practical wisdom for building a more meaningful future.

Watch now and discover what might be waiting on the other side of success.

Timestamps:
(01:14) Meet Edward Sullivan
(02:34) What Makes a Great Coach?
(04:54) AI Anxiety and Burnout
(06:44) Tuning the Instrument
(08:37) Coaching Young Founders
(09:42) Wisdom and Age Diversity
(12:49) Building Intergenerational Teams
(17:16) Curiosity Before Advice
(20:11) Midlife and the Happiness Curve
(22:37) Right-Sizing Expectations
(24:32) Why Success Can Feel Empty
(28:56) The Power of Small Experiments
(32:17) Designing a Meaningful Life
(35:43) Advice for New Coaches
(37:57) The Business of Coaching
(40:16) Finding Your Coaching Niche
(41:32) A Lesson Learned the Hard Way
(43:41) What Now Workshop
(44:18) Building a Career Crescendo
(45:38) Closing Thoughts

Learn more about MEA at ⁠https://www.meawisdom.com/
Workshop with MEA in March 2027: https://www.meawisdom.com/workshop/what-now-finding-passion-and-purpose-after-a-big-success-march-2027/

#LifeAfterSuccess #WhatNow #PurposeAndMeaning #ExecutiveCoaching #LeadershipDevelopment #CareerTransition #PersonalGrowth #MidlifeTransition #SuccessfulButUnfulfilled #SelfDiscovery #MeaningfulLife #ModernElder #ChipConley #EdwardSullivan #VelocityCoaching

Your job title tells people what you do. The problem you care about tells them who you are.

Arun Gupta, CEO of NobleReach and co-author of The Mission Generation, joins Chip Conley for a thoughtful conversation about finding purpose, staying curious, and creating a meaningful career at every stage of life.

Some of the ideas they explore:
Why following your energy can lead you somewhere a career plan never could
How becoming a beginner again can bring fresh energy to midlife
Why learning, earning, and giving back can happen throughout our lives
What younger generations can teach us about work and purpose
Why our most human strengths matter even more in the age of AI

From leaving a 20-year career in venture capital to stepping into the vulnerability of teaching and public service, Arun shares why the next chapter doesn’t need to be mapped out before you begin it.

Watch the full episode of The Midlife Chrysalis.

Timestamps:
(03:39) Arun Gupta’s Mission-Driven Journey
(09:05) From India to Venture Capital
(12:50) Why Careers Don’t Follow a Straight Path
(16:28) What Gen Z Is Teaching Us
(20:33) Rethinking Learn, Earn, and Return
(22:33) Finding New Purpose Later in Life
(25:07) What Makes a Great Mentor
(29:24) Learning Across Generations
(33:23) AI and the Future of Work
(36:17) Building Human Capital in the AI Age
(39:25) Arun’s Midlife Career Reinvention
(43:46) What Problem Do You Care About?
(47:24) Doing Good and Doing Well
(49:00) Rebuilding Trust Through Interdependence

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

#ArunGupta #ChipConley #MidlifeChrysalis #TheMissionGeneration #NobleReach #CareerReinvention #PurposeDrivenCareer #MidlifeCareer #FutureOfWork #IntergenerationalMentorship #LifelongLearning #AIAndWork #CareerPurpose #MeaningfulWork #SecondAct

What if the thing that makes you different has been there all along, you just haven’t named it yet?

In this Wisdom Wednesday, Chip Conley and Derek Gehl explore how to “excavate your essence” and uncover the unique gift that can guide your work, choices, and life.

You’ll discover:
How Airbnb uncovered “Belong Anywhere” by looking beyond what the company does to why it matters
A simple five-question exercise for getting beneath the obvious answers
How Chip discovered his gift as a “social alchemist” and used it to better understand his path
Why other people and the right environment can help you see what’s difficult to uncover alone

Your essence isn’t something you need to invent. It’s something you can uncover.

Watch now and ask yourself: What gift can I offer?

Timestamps:
(00:00) Welcome to Wisdom Wednesday
(01:45) How to Excavate Your Essence
(02:04) What Makes You Different?
(04:04) The Five Questions Exercise
(04:59) How Airbnb Found Its Essence
(06:28) What Gift Can You Offer?
(08:00) Discovering Your Unique Gift
(10:38) Let Your Essence Guide You
(12:09) Why You Can’t Do This Alone
(14:31) Make Space for an Epiphany
(14:54) Try the Essence Exercise

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

#ChipConley #MidlifeChrysalis #WisdomWednesday #ExcavateYourEssence #FindYourGift #MidlifePurpose #SelfDiscovery #ModernElderAcademy #MEA #PersonalGrowth #MidlifeWisdom #FindYourEssence #UniqueGifts #PeterDrucker #SocialAlchemist

How do you find common ground with someone you profoundly disagree with?

At a time when political, religious, and cultural divisions seem deeper than ever, peacebuilder Shamil Idriss, CEO of Search for Common Ground, shares what decades of bringing people together have taught him about trust, conflict, and human connection.

In this conversation with Chip Conley, Shamil explores:
Why being heard and respected matters more than being agreed with
How building trust before a crisis can bridge even deep divides
Why curiosity is more powerful than judgment
How taking just one meaningful action can restore hope
Why today’s breakdown may ultimately lead to breakthrough

From global conflicts to disagreements in our own communities, Shamil offers a hopeful reminder that our futures are interconnected, and that each of us can help build common ground.

Watch now to discover how connection can begin, even when we disagree.

Timestamps:
(03:50) Meet Shamil Idriss
(04:55) The Beginning of Peacebuilding Journey
(08:48) Inside the UN Alliance of Civilizations
(11:02) Why Our Futures Are Connected
(15:07) How to Build Common Ground
(19:40) What Can We Do Together?
(21:39) How Trust Is Built Across Differences
(24:07) Being Heard Matters More Than Agreement
(26:19) Curiosity Instead of Judgment
(29:10) Why Peacebuilding Is Harder Today
(32:00) The Power of Doing One Thing
(36:48) How to Hold On to Hope
(40:38) A Lifetime of Lessons

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

#ShamilIdriss #SearchForCommonGround #Peacebuilding #CommonGround #PoliticalPolarization #ConflictResolution #BridgingDivides #BuildingTrust #CulturalCuriosity #HumanConnection #Dialogue #MidlifeWisdom #Ubuntu #SocialCohesion #ChipConley

Midlife isn't the beginning of the end. For more than 50 years, Dr. Ken Dychtwald, psychologist, bestselling author, and founder of Age Wave, has studied what it really means to grow older.

In this conversation, he explains why midlife isn't the beginning of the end, but the start of one of life's most meaningful transformations.

In this episode, you'll discover:
Why midlife is a time of growth, not decline
The powerful idea of "middle essence" and how it changes the way we think about aging
Why retirement may be one of today's biggest myths
How purpose becomes even more important as we get older
The simple advice Ken believes can help anyone build a richer, more meaningful life

If you're navigating midlife or wondering what's possible in the years ahead, this conversation will change the way you think about aging.

Enjoyed this episode? Subscribe, leave a review, and share it with someone who needs this message.

Timestamps:
(03:39) Ken Dychtwald's Early Journey
(08:31) The Exercise That Changed His Career
(10:42) Predicting the Age Wave
(14:55) Why Ageism Persists
(16:34) Midlife Is a Chrysalis
(18:05) The Case for "Middle Essence"
(20:55) Why Society Doesn't Support Midlife
(25:41) Ken's Midlife Lessons
(29:56) Why He Never Retired
(31:00) The Untapped Purpose of Older Adults
(33:10) The Two Books Everyone Should Read
(34:54) Advice for Chip Conley
(36:38) Why Deep Questions Matter
(37:22) The Future of Midlife
(40:01) Think Bigger Than Yourself
(42:18) Love, Mentors, and Lifelong Relationships

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

#KenDychtwald #MidlifeTransformation #MiddleEssence #SecondHalfOfLife #PurposeAfter50 #AgeWave #Retirement #Ageism #PsychologyOfAging #HumanPotential #PersonalReinvention #ChipConley #Elderhood #Midlife #Purpose