Episode 43

December 17, 2025

Chip Conley

Inside the Messy Middle: What Actually Drives Transformation in Midlife

Inside the Messy Middle: What Actually Drives Transformation in Midlife

Feeling stuck in midlife? You might be in your chrysalis, not a crisis.

In this Wisdom Wednesday episode, Chip Conley breaks down why midlife often feels confusing and heavy, and why that “messy middle” is actually the beginning of real transformation.

Chip shares:

  • The three stages of every transition and where most people get stuck
  • What really happens inside the messy middle
  • Why men and women experience midlife so differently
  • How transitional intelligence (TQ) helps you move forward with clarity

If you’re wondering whether something is wrong, or whether you’re simply evolving, this episode offers the reassurance and perspective you need. If you enjoyed this, follow the show, leave a rating, and join us next week for more Wisdom Wednesday insights.

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