Episode 76

March 4, 2026

Chip Conley

Letting Go in Midlife: What Has Run Its Course?

Letting Go in Midlife: What Has Run Its Course?

Midlife isn’t about adding more. It’s about letting go.

In this Wisdom Wednesday episode of The Midlife Chrysalis, Chip Conley joins Derek Gehl to explore The Great Midlife Edit, the courage to release what has quietly run its course.

Drawing from his near-death experience and the sale of his company, Chip shares what it really means to “empty your cup” and create space for what’s next.

In this conversation, you’ll learn:

  • Why midlife shifts us from accumulation to editing
  • How to recognize what’s ready to “graduate” from your life
  • The three stages of transition — endings, the messy middle, and new beginnings
  • A powerful question to help you begin your own edit

If something in your life feels heavy, outdated, or complete, this episode is your gentle invitation to let go and begin again.

Listen in, reflect, and share it with someone ready for their next chapter.

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