THE NON-OBVIOUS SHOW · EPISODE 80

Having Wild Courage To Get What You Want

with Jenny Wood

Episode 80 · June 2, 2026 · 35 min

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.

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Episode Summary

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Key Takeaways

01Wild courage involves embracing traits society often discourages.
02In-person interactions can reveal authentic personality traits that virtual can't.
03Being shameless and bossy can be strategic in leadership if used appropriately.
04Cultural context influences how wild courage traits are perceived.
05Living 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 ↗