Episode 109

May 20, 2026

Chip Conley

Why So Many Successful People Struggle With Retirement

Why So Many Successful People Struggle With Retirement

Why So Many Successful People Struggle With Retirement
What Comes After Ambition but Before Retirement?
The Hidden Midlife Crisis Between Success and Retirement

What happens when you stop chasing success… but you’re not ready to retire?

In this episode of Midlife Chrysalis, Chip Conley and Derek Gehl explore a stage of life many people experience but rarely talk about: feeling caught between ambition and retirement.

Chip shares personal stories about aging parents, purpose, and how his own view of success changed over time. He explains why midlife can become less about proving yourself and more about giving back, mentoring others, and finding deeper meaning.

In this episode:

  • Why traditional success can start feeling empty
  • The difference between ambition and purpose
  • Why retirement doesn’t work for everyone
  • How to discover what really matters in the next chapter of life
  • A simple question that can help you find your calling

If you’re rethinking what success, purpose, and aging really mean, this episode is for you.

Watch now.

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