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Don't Be Boring, Here's the Fix: Storytelling 101


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Episode 54: "Don't Be Boring, Here's the Fix: Storytelling 101"

Ever watched someone's eyes glaze over the second you started talking? You're not imagining it. And it's fixable.

Episode Description

This year, two interviews landed on Shelly's calendar that felt like a dream to book. Both guests are good people living lives of real service. Both conversations still fell flat, and not because of who they were.

In this solo episode, Shelly unpacks what those two conversations had in common, and holds it up against a very different reaction from early in the show's history, a conversation with an eleven-time New York Times bestselling author that still stands as one of the best interviews on the podcast. The difference wasn't credentials. It was storytelling.

You'll walk away with a new way to think about who owns your story, who doesn't, and the one shift that turns "talking about yourself" into a story people lean into instead of tune out of.

Chapters

00:00 Welcome and Promise

01:22 Two Interviews Fell Flat

03:09 Donald Miller Breakthrough

05:39 Why Stories Hook Us

09:10 Zoom In on Stakes

11:43 Permission vs Craft

15:48 Interviewer Skill Gap

17:09 Three Questions to Open Up

21:21 Takeaways and Closing

Key Topics

  • Why the most accomplished people can still tell a boring story
  • The difference between owning your story and earning permission to tell it
  • What good storytelling borrows from Save the Cat and The Seven Basic Plots
  • Why the interviewer's own skill matters as much as the guest's story

Next Week: Episode 55 — Andy Stumpf, US Navy SEAL (ret.)

Resources & Links

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