The Lifestyle Investor - Investing, Passive Income, Wealth

248: How to Lead With Wild Courage (Even If You’re Afraid) with Jenny Wood

Jul 24, 2025
Jenny Wood, author of 'Wild Courage' and a former Google executive, shares her journey from corporate success to personal fulfillment. She challenges the notion that negative traits like selfishness and manipulation are weaknesses, framing them instead as tools for influence and growth. Jenny reveals nine unconventional traits that embody Wild Courage and discusses the importance of mindset shifts in overcoming fear. Her insights offer a fresh perspective on leadership, showing how embracing audacity can unlock opportunities and lead to a more fulfilling life.
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ANECDOTE

Subway Chase Sparks Wild Courage

  • Jenny Wood shared a story about chasing a man off a New York subway as a moment of wild courage.
  • This impulsive act led to marriage and sparked her habit of boldly pursuing what she wants.
INSIGHT

Courage Is Learned Not Innate

  • Wild courage is a learned skill, not an innate trait or absence of fear.
  • Anyone can develop it by feeling fear and taking action despite it.
ADVICE

Manage Higher and Diagonally

  • Develop relationships with your boss's boss and their peers for influence and career growth.
  • Mentors talk to you; sponsors advocate for you behind the scenes during promotions and decisions.
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