309: How to Lead With Wild Courage

Finding Brave

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 InstagramJenny Wood on FacebookJenny Wood on Threads

Jenny Wood on XWild 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 JurasekCheck out Kathy’s conversation with Jordan Friedman in Episode 308: Powerful Stress Management Approaches Designed for Times Like These

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FINDING BRAVE PODCAST AD FOR KATHY AND JORDAN’S CENTRAL PARK RETREAT DATE - JUNE 13, 2025

Join us June 13th, 2025 for a LIVE, calming in-person retreat in NYC’s iconic Central Park - hosted by Kathy Caprino and Jordan Friedman

Connect with Your Inner Calm on June 13th with Kathy and Jordan, in NYC’s iconic Central Park

I’m thrilled to announce an event that’s truly special coming up on June 13th, designed for folks who would like a stress-reducing, calm and enlivening retreat experience in NYC’s Central Park!

For the first time, I'm teaming up with my dear friend and top stress management expert, Jordan Friedman (who I’ve had the honor of interviewing on my podcast twice now) to offer a live retreat and tour experience on June 13th in the heart of New York City's iconic Central Park.

We’ll start with an 2 and ½ -hour walking tour guided by Jordan (who is also a fabulous licensed New York City tour guide) of some of the most beautiful and relaxing spots in the park, followed by an energizing and supportive Q&A session, where Jordan and I will help you directly address and navigate some of the biggest stressors you’re facing today — in your life, career, and family.

We cannot wait to spend this special and meaningful time with you, surrounded by the nature, beauty, and deep calm of the urban oasis of Central Park.

Spots are limited, so check out the details and register today at thestresscoach.com/central-park-retreat.

Jordan and I would love to offer you this special experience on June 13th!

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I bring all of that experience to our work together, helping you build a new chapter that aligns with who you really are and what you’re ready to create.

Check out kathycaprino.com/careerbreakthru and I hope you’ll register now. I’d love to support you this month and beyond!!

And don’t forget to leverage Kathy Caprino AI - my new digital career coaching tool - for instant access to answers and guidance about your most pressing career and leadership growth challenges.

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Order Kathy’s book The Most Powerful You today!

If you enjoy the book, we’d so appreciate your giving the book a positive rating and review on Amazon! And check out Kathy’s digital companion course The Most Powerful You, to help you close the 7 most damaging power gaps in the most effective way possible.

Kathy’s Power Gaps Survey, Support To Build Your LinkedIn Profile To Great Success & Other Free Resources

Kathy’s TEDx Talk, Time To Brave Up & Free Career Path Self-Assessment

Kathy’s Amazing Career Project video training course & 6 Dominant Action Styles Quiz

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Key Quotes from today’s episode:

“The same theme kept coming up when people felt stuck [and] that theme was fear: fear of failure, fear of uncertainty, and fear of judgment [from] others.” — @itsjennywood [0:08:28]

“You don't need permission from somebody else to do these things, to take these bold actions.” — @itsjennywood [0:28:23]

“That same bravery, that same wild courage that pushed me to make that ask, is the same wild courage that pushes me to make other asks or requests or bold moves, and then sometimes they work out!” — @itsjennywood [0:31:33]

“It's better to learn from your mistakes than to waste time predicting the consequences of every possible decision or outcome. So, think fast and fearless, and if you're on the fence, do it.” — @itsjennywood [0:32:29]

“I have found that when I have been the most successful, it's [been] because I was willing to be on the edge of discomfort.” — @itsjennywood [0:32:53]

“There's this disconnect between what's real and what we feel, and that's why I say ‘we have to give permission to ourselves to be selfish, to be reckless, to be bossy.’” — @itsjennywood [0:39:02]

Watch our Finding Brave episodes on YouTube!

Don’t forget – you can experience each Finding Brave episode in both audio and video formats! Check out new and recent episodes on my YouTube channel at YouTube.com/kathycaprino. And please leave us a comment and a thumbs up if you like the show!