Episode 100

April 29, 2026

Chip Conley

Why Success Stops Making You Happy After 40

Why Success Stops Making You Happy After 40

You checked all the boxes… so why does something still feel off?

In this episode, Chip Conley and Derek Gehl explore what happens when success stops feeling like success, and why so many people hit this wall in midlife. And what you can do when you get there

Here’s what you’ll learn:

  • The 3 questions that reveal your true direction
  • Why achievement alone doesn’t lead to fulfillment
  • The hidden trap of defining success through work
  • Why relationships matter more than you think
  • How to start redefining success in a way that actually feels good

It’s a bold, thought-provoking conversation about slowing down, letting go, and trusting what unfolds next.

Watch now and consider: when was the last time you gave yourself space like this?

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