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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/
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