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The Non-Obvious Show · Episode 80

Having Wild Courage To Get What You Want

with Jenny Wood

Episode 80 · June 2, 2026 · 35 min

In This Episode

Explore the unconventional traits of wild courage with Jenny Wood, a NYT best-selling author and founder of Google's Own Your Career program. Discover how embracing weirdness, selfishness, shamelessness, and other traits can propel your career and life forward.

Key Takeaways

  • Wild courage involves embracing traits society often discourages.
  • In-person interactions can reveal authentic personality traits that virtual can't.
  • Being shameless and bossy can be strategic in leadership if used appropriately.
  • Cultural context influences how wild courage traits are perceived.
  • Living with wild courage reduces regrets and maximizes life experiences.

What We Cover

  • 00:00The Courage to Chase Opportunities
  • 02:42Embracing Wild Courage
  • 03:52The Nine Traits of Wild Courage
  • 06:14The Importance of In-Person Connections
  • 07:53Candor and Tough Conversations
  • 10:40Cultural Context of Boldness
  • 12:17Survivorship Bias in Career Advice
  • 16:38Living Without Regrets
  • 19:26Planning a Family Adventure
  • 20:22Teaching Kids About Courage
  • 22:27Gender Dynamics in Career Advice
  • 25:55From Big Ideas to Actionable Tips
  • 27:25Career vs. Life Advice
  • 30:35Simplifying Life and Priorities

About The Guest

Jenny Wood Author of Wild Courage; former Google executive

Jenny Wood is the author of Wild Courage: Go After What You Want and Get It, and founder of Own Your Career. She spent nearly two decades as an executive at Google and now writes and speaks about ambition, confidence and career growth.

itsjennywood.com ↗

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