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The Path Is Made By Walking episode artwork

Jul 10, 2026 10 min

The Path Is Made By Walking

from Rewriting Reality, With Chase Tolleson Hosted by Chase Tolleson

If you’ve ever reached a goal and felt… nothing, this one will hit close to home. We start with Antonio Machado’s poem about the traveler who makes the path by walking, then use it to shine a light on a problem I see constantly in the coaching and entrepreneur world: people building impressive businesses on someone else’s blueprint, then waking up to realize they’re farther from themselves than ever. We talk about what happens when you’re doing $40k, $50k, $70k months and the fulfilment still doesn’t arrive. Money can create comfort, but it can’t fill a “not enough” hole. Instead, it often stacks up next to the gap, leaving you staring at the distance between who you’ve believed you are and what you’ve managed to build. We dig into why “it’s never enough” is usually a projection, how work can become a personal rat race, and why “highest self” language can turn into a polished way to avoid looking at what hurts. From there we pivot to what actually changes things: clearing guilt, shame, anger, and sadness so faith can become real, practical, and lived. We unpack the difference between useful structure and frameworks that bury your instincts, then land on a simple practice that sounds almost too easy: let it happen. If you’re ready to stop chasing alignment and start walking your own path, press play. Subscribe, share this with a friend who’s stuck on someone else’s “should,” and leave a review with the question you’re wrestling with right now. Ready to Rewrite Reality? Click here

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If you’ve ever reached a goal and felt… nothing, this one will hit close to home. We start with Antonio Machado’s poem about the traveler who makes the path by walking, then use it to shine a light on a problem I see constantly in the coaching and entrepreneur world: people building impressive businesses on someone else’s blueprint, then waking up to realize they’re farther from themselves than ever. We talk about what happens when you’re doing $40k, $50k, $70k months and the fulfilment stil...

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The Path Is Made By Walking

0:00 10:06

Chapters

  1. 0:00 A Poem About Making A Path
  2. 0:20 When Success Pulls You Off Course
  3. 0:51 Money Cannot Fill Not Enoughness
  4. 3:09 The Personal Rat Race We Hide In
  5. 5:54 Faith, Letting Go, And True Alignment
  6. 9:29 Why Frameworks Can Bury Your Life
  7. 9:45 Where To Find The Video Version

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How long is this episode of Rewriting Reality, With Chase Tolleson?

This episode is 10 minutes long.

When was this Rewriting Reality, With Chase Tolleson episode published?

This episode was published on July 10, 2026.

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