AI Summary
5 min readEdward Sullivan, a veteran executive coach who runs Velocity Coaching, has spent years working with founders and CEOs at companies like DoorDash, Sweetgreen, and Geico. But the pattern he sees most often among his clients is not a failure to achieve goals—it is the emptiness that follows success. People get everything they wanted and then ask, “Is that all there is?” That question is the center of the conversation between Sullivan and host Chip Conley on this episode of The Midlife Chrysalis.
The Post-Success Dip and the “What Now” Question
Sullivan describes a phenomenon he calls “post-party depression.” After his own book Leading with Heart came out to strong reviews, speaking engagements, and Harvard Business Review articles, the excitement stopped. “It just went back to silence and back to normal life,” he says. The dopamine hits vanished. A stranger at a conference had warned him: “Get ready for the dip.” Sullivan dismissed it. Then it hit him six months later.
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What you'll learn
- 1 (00:00) **Opening: The Paradox of Success** - Edward Sullivan introduces the core theme: achieving everything you wanted can leave you feeling empty.
- 2 (01:52) **What Makes a Great Coach** - Sullivan defines the core attributes of effective coaching, emphasizing curiosity and honesty over giving answers.
- 3 (05:50) **The Post-COVID Coaching Landscape** - The biggest challenges facing leaders today, from AI anxiety to extreme work cultures.
- 4 (07:10) **Tuning the Instrument** - The foundational principle for any leader: self-care before team-care before culture.
- 5 (08:32) **The Intergenerational Tension** - Why age-diverse companies struggle and how to bridge the gap between young founders and older executives.
- 6 (12:53) **Advice for the Younger CEO** - How to effectively integrate an older, senior hire into a young organization.
- 7 (14:02) **Advice for the Older Worker** - How to enter a young company without alienating the team.
+ Full timestamped outline available in the app
Guests on this episode
Show Notes
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
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