S18: E15: Embarrassment is the Cost of Entry

S18: E15: Embarrassment is the Cost of Entry

From Old Fashioned On Purpose by Jill Winger

April 20, 2026 · 29 min · Season 18 · Episode 15

About this episode

Jill Winger discusses the challenges and lessons learned from being a beginner at roping at 40, emphasizing that embarrassment is a necessary part of growth.

Learning to rope at 40 has humbled me in all the best and worst ways, because nothing exposes your ego faster than being a beginner in front of people who’ve been doing something their whole lives. In this episode, I’m talking about a phrase I’ve been repeating to myself in the branding pen: embarrassment is the cost of entry. We’ll explore what this phrase means, why so many of us feel threatened by embarrassment, our addictions to competence, the messy stage of growth, and the wonderful rew...

People in this episode

Host: Jill Winger

Topics covered

  • embarrassment
  • beginner's journey
  • personal growth
  • ego
  • competence
  • branding

Keywords

  • roping
  • embarrassment
  • personal development
  • ego
  • competence
  • growth
  • branding

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