About this episode

Chip Conley and Edward Sullivan discuss the challenges of finding meaning after achieving success in midlife.

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…

People in this episode

Host: Chip Conley

Guest: Edward Sullivan

Topics covered

• success
• midlife challenges
• personal growth
• AI in leadership
• self-care
• meaningful life

Mentioned in this episode

Organizations: Velocity Coaching

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• From Doing to Being: The Power of Presence | Teddi Dean · September 4, 2026 · 50 min
• Curiosity Is the Secret to a Richer Life · September 2, 2026 · 24 min
• We’re Living Longer. Why Isn’t Society Ready? | David Sinclair · August 31, 2026 · 45 min
• From Achievement to Fulfillment: Building Your Life 3.0 | Seth Streeter · August 28, 2026 · 48 min

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