Episode 133

July 15, 2026

Chip Conley

What Your Future Self Wants You to Know About Life

What Your Future Self Wants You to Know About Life

Have you ever wondered what your 80 year old self would tell you today?

In this episode, Derek and Chip talk about aging, relationships, purpose, and the life lessons that only become clear with time. Through a powerful exercise imagining a conversation with his future self, Chip shares the insights that have reshaped how he thinks about success, love, health, and what truly matters.

In this episode, you'll discover:

  • Why talking to your future self can help you make better decisions today.
  • The surprising relationship lesson that completely changed Chip's perspective on growing older.
  • How a simple journaling exercise unlocked unexpected insights and self reflection.
  • Why success, legacy, and achievement become less important than the people you grow with.
  • How your priorities naturally evolve as you move through the second half of life.

If you're navigating midlife, rethinking your priorities, or simply looking for a fresh perspective on what makes a meaningful life, this conversation is full of wisdom you won't want to miss.

 🎧 Watch the full episode and join the conversation.

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