309: How to Lead With Wild Courage

Too often, the traits we’re taught to tone down are the very ones that can drive our boldest breakthroughs. In this powerful episode, we explore what it truly means to lead and live with wild courage. Dismantling conventional career advice, Jenny Wood champions a more audacious path to success, one built on traits long considered too disruptive or inappropriate to embrace.

Jenny Wood is a New York Times bestselling author, speaker, and former Google executive who built one of the company’s largest career development programs. Her new book, Wild Courage: Go After What You Want and Get It, dives into nine controversial traits, from reckless to bossy, that ambitious professionals can reclaim and reframe to be better leaders and reach their full potential. With a background in research at Harvard Business School and features in Forbes, HBR, and Bloomberg, Jenny brings both insight and irreverence to the table, along with a serious talent for cutting through the noise.

Through stories both personal and professional, Jenny illustrates how fear of failure, uncertainty, and judgment often keeps us playing small. Whether it’s chasing down a stranger on a subway (now her husband), asking a C-suite executive for mentorship, or launching a career-defining program at Google, she shows how reclaiming so-called negative traits like "shameless" or "reckless" can become a source of power and clarity.

This episode is a candid, empowering reminder that growth begins on the edge of discomfort. Jenny shares tools to rewrite the internal stories that hold us back, and reframes boldness as a skill that can be practiced, not just a trait you’re born with.

If you’re ready to stop waiting for permission and start leading with more courage in your career and life, this conversation is a must-listen!

 

Key Highlights From This Episode:

• What inspired Wild Courage and the bold subway moment that changed Jenny’s life. [04:35]
• How fear showed up again and again in Jenny’s coaching with professionals. [07:41]
• Enacting wild courage and why it might be more challenging for certain groups. [11:50]
• The nine controversial traits of wild courage and how to reframe and reclaim them. [12:41]
• How the seeds were planted for wild courage in Jenny’s childhood. [15:21]
• Ways that shame holds us back and tips for de-shaming your language. [19:45]
• A candid look at how overthinking fuels self-judgment and fear. [24:29]
• Tools and internal resources to reframe fear, shame, and self-doubt. [27:15]
• The reckless trait, why Jenny struggles with it, and how she’s learned to embrace it. [32:01]
• Why we need to give ourselves permission to be selfish, reckless, and bossy. [36:53]

 

For More Information:

Jenny Wood

Jenny Wood on LinkedIn

Jenny Wood on Instagram
Jenny Wood on Facebook
Jenny Wood on Threads

Jenny Wood on X
Wild Courage: Go After What You Want and Get It

 

Links Mentioned in Today’s Episode: 

Listen to Episode 271: How to Recognize and Release the Damaging Shame You Hold with David Jurasek
Check out Kathy’s conversation with Jordan Friedman in Episode 308: Powerful Stress Management Approaches Designed for Times Like These

 

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