The Lifestyle Investor - Investing, Passive Income, Wealth

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


Listen Later

What if the very traits you've been taught to hide—like being selfish, nosy, or even manipulative—are actually your greatest unfair advantage?

That’s the bold idea Jenny Wood explores in Wild Courage—a framework she developed after nearly two decades at Google, where she rose through the ranks, led billion-dollar business units, and launched initiatives that reached over 50,000 employees across 100+ countries.

Eventually, success on paper wasn’t enough. Jenny felt burned out and boxed in—stuck between achievement and alignment. That turning point led her to redefine what real courage looks like in business and life.

In this episode, she unpacks the 9 traits society often labels as “too much” or “too aggressive”—and shows how to reclaim them as strategic tools for influence, opportunity, and a life you actually want. Whether you’re looking to land the promotion, launch your business, or stop playing small, this conversation will challenge everything you thought you knew about confidence, leadership, and courage.


In this episode, you’ll learn: 


1.) The wild subway story that changed Jenny’s life—and the mindset shift that helped her take bold action in the face of fear.

2.) Discover the 9 unconventional traits that define Wild Courage—and how they unlock greater influence, freedom, and business growth.

3.) Why “manipulative” might be your most powerful leadership trait—and how to use it to build trust, influence, and high-leverage relationships.

4.) Why replacing your salary may be the wrong goal—and how to build confidence, earn through passive income, and design a life that truly aligns with what matters most.


Show Notes: LifestyleInvestor.com/248


Tax Strategy Masterclass

If you're interested in learning more about Tax Strategy and how YOU can apply 28 of the best, most effective strategies right away, check out our BRAND NEW Tax Strategy Masterclass: www.lifestyleinvestor.com/tax


Strategy Session 

For a limited time, my team is hosting free, personalized consultation calls to learn more about your goals and determine which of our courses or masterminds will get you to the next level. To book your free session, visit LifestyleInvestor.com/consultation


The Lifestyle Investor Insider

Join The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insider


Rate & Review

If you enjoyed today’s episode of The Lifestyle Investor, hit the subscribe button on Apple PodcastsSpotifyor wherever you listen, so future episodes are automatically downloaded directly to your device. You can also help by providing an honest rating & review.


Connect with Justin Donald

  • Facebook
  • YouTube
  • Instagram
  • LinkedIn
  • Twitter



See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

...more
View all episodesView all episodes
Download on the App Store

The Lifestyle Investor - Investing, Passive Income, WealthBy Justin Donald

  • 4.9
  • 4.9
  • 4.9
  • 4.9
  • 4.9

4.9

282 ratings


More shows like The Lifestyle Investor - Investing, Passive Income, Wealth

View all
BiggerPockets Real Estate Podcast by BiggerPockets

BiggerPockets Real Estate Podcast

16,778 Listeners

The Real Estate Guys Radio Show - Real Estate Investing Education for Effective Action by The Real Estate Guys

The Real Estate Guys Radio Show - Real Estate Investing Education for Effective Action

711 Listeners

The Best Ever CRE Show by Joe Fairless

The Best Ever CRE Show

992 Listeners

Get Rich Education by Real Estate Investing with Keith Weinhold

Get Rich Education

601 Listeners

Main Street Business by Mark J Kohler and Mat Sorensen

Main Street Business

583 Listeners

Real Wealth Show: Real Estate Investing Podcast by Kathy Fettke / RealWealth

Real Wealth Show: Real Estate Investing Podcast

412 Listeners

Tax Smart Real Estate Investors Podcast by Hall CPA

Tax Smart Real Estate Investors Podcast

423 Listeners

The WealthAbility Show with Tom Wheelwright, CPA by The Rich Dad Media Network

The WealthAbility Show with Tom Wheelwright, CPA

518 Listeners

Ken McElroy Show by Ken McElroy

Ken McElroy Show

721 Listeners

Real Estate Rookie by BiggerPockets

Real Estate Rookie

1,832 Listeners

PassivePockets: The Passive Real Estate Investing Show by PassivePockets, Jim Pfeifer, and Left Field Investors

PassivePockets: The Passive Real Estate Investing Show

129 Listeners

On The Market by BiggerPockets

On The Market

903 Listeners

Action Academy | Millionaire Mentorship For Your Life & Business by Brian Luebben

Action Academy | Millionaire Mentorship For Your Life & Business

697 Listeners

The BetterLife Podcast by Brandon Turner and Cam Cathcart

The BetterLife Podcast

839 Listeners

The David Greene Show by David Greene

The David Greene Show

698 Listeners