321: How to Be a Likeable Badass
Finding Brave
What if the very traits you’ve been told to soften, like being collaborative or agreeable, are actually essential to your success, not obstacles to it? In this episode of Finding Brave, we explore why so many professionals, especially women, feel trapped between being liked and being respected, and what it really takes to be both. In this episode, Kathy Caprino speaks with , an organizational psychologist, professor at the University of North Carolina Kenan-Flagler Business School, and bestselling author of . Drawing on her extensive research on status, power, negotiation, and influence,...
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320: Be Yourself at Work: Show Up, Stand Out, and Lead from the Heart
Finding Brave
What does it really mean to be yourself at work without hiding, performing, or shrinking to fit expectations? In this Finding Brave conversation, we explore why authentic presence is not a soft skill or a personal indulgence, but a powerful leadership practice that builds trust, connection, and impact in today’s fast-moving, emotionally complex workplaces. Today’s inspiring guest is , the world’s first Chief Heart Officer at VaynerX, where she partners with CEO Gary Vaynerchuk to shape culture and leadership at scale. A sought-after speaker and the author of , Claude brings a...
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319: A Talent for Giving: Creating a More Generous Society for All
Finding Brave
The world around us has transformed dramatically—but has philanthropy kept up? For our Finding Brave guest today, , American-British investor and humanitarian and the author of the new book , this question isn't academic—it's deeply personal. His philanthropic journey began humbly, volunteering at a soup kitchen as a teenager. Today, he's recognized globally for transformative work addressing homelessness through London's Passage Day Centre and championing emerging artists through the . In the U.S., he serves on the boards of The J. Paul Getty Trust, St. Patrick's Cathedral, and the...
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318: How Organizations Need to Change Their Narrative In Challenging Times
Finding Brave
Everybody wants to believe in something, but the truth is, if you're a leader who shies away from asking tough questions, you're making it harder for people to believe in you. In this Finding Brave episode, we are joined by , known as the Rapid Growth Guy and storytelling expert responsible for five multi-million dollar business success stories. He is the author of and has been featured in Forbes and listed by Global Gurus as one of the Top 30 Sales Professionals. In this conversation, we explore what it truly means to lead through authentic, compelling story, not spin. Matthew unpacks how...
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317: How to Attract Great Investors For Your Products and Business
Finding Brave
Protecting your ideas is a critical step for attracting excellent aligned investors. In this episode of Finding Brave, I sit down with intellectual property expert and attorney , senior partner at , to demystify what it really takes to secure funding and safeguard innovation. Drawing on his extensive experience helping inventors, entrepreneurs, and creative professionals, David shares how a strong IP strategy serves as both protection and proof of your business’s credibility. A registered patent attorney and professor at Temple University, Parsons School of Design, and Radzyner Law School,...
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316: Taking the Brave Leap to Live Your Life Purpose
Finding Brave
Why would someone walk away from a lucrative, 15-year career in software engineering? For , it came down to one thing: learning to prioritize the "spirit mind" over the "material mind.” That perspective shift gave him the inner clarity—and the bravery and courage—to finally move into a life and career of deeper purpose. Jeffrey is a spiritual teacher and energy healer whose work has empowered thousands of people, through ’s Healing Programs and through his own courses, trainings and years of individual and group work with thousands of people around the globe. His mission is to make...
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315: FAWNING: Why the Need to Please Makes Us Lose Ourselves
Finding Brave
On the surface, you may look like the model employee, partner, or friend: always dependable, always agreeable. But beneath the surface, you may be carrying a lifetime of survival strategies that keep you invisible in your own life. This is the story knows both personally and professionally, and it’s the story she helps so many of us begin to rewrite. Dr. Ingrid Clayton is a licensed clinical psychologist with advanced degrees in transpersonal and clinical psychology. She has maintained a thriving private practice for more than fifteen years and writes the popular Psychology Today blog, ,...
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314: You Are Not Your Trauma: How You Can Heal Your Life Experience
Finding Brave
What if the parenting behaviors you dislike most in yourself aren’t really “you”? What if they’re trauma responses your brain learned long ago to survive, and what if you could change them? In this episode of Finding Brave, explores how trauma shapes our parenting and what we can do to change the cycle. Dr. Koslowitz is a trauma expert, child psychologist, and author of the new book . She treats children, adolescents, and families at the , and hosts the Post-Traumatic Parenting and . In this conversation, she explains how trauma responses can surface in family life through yelling,...
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313: 8 Superpowers for Thriving in Constant Change
Finding Brave
Uncertainty has become the defining condition of our time, yet most of us still struggle to find our footing in it. What if you could reframe change itself as a source of strength? Today on Finding Brave, we’re joined by global change advisor, futurist, and author to uncover how to cultivate a “flux mindset” and discover the hidden opportunities within constant change. April, a World Economic Forum Young Global Leader and one of Forbes’ 50 Leading Female Futurists, is a trusted advisor to organizations from Airbnb and Nike to the World Bank. She is the author of , a book that helps...
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312: How Confidence Is The Key and How You Can Get It, Build It and Keep It
Finding Brave
Thank you for listening to our Finding Brave show, ranked in the Top 100 Apple Career Podcasts! “Whether you’re on an athletic team, a sales force, or a symphony orchestra, you better be honest about what you think about yourself. What you think about yourself and what you think about all the things that happen day by day, that’s what constitutes your confidence.” – Dr. Nate Zinsser Confidence is a character trait that has relatively little to do with what happens to you, but rather it’s a function of how you think. Today’s Finding Brave guest reveals how you can change your...
info_outlineToo 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 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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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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READY FOR A HUGE PERSONAL SHIFT TO ACHIEVE MORE SUCCESS, IMPACT, AND FULFILLMENT IN YOUR CAREER THIS YEAR?
Work with Kathy and get hands-on, transformative CAREER & LEADERSHIP GROWTH COACHING SUPPORT today!
Are you ready for a big positive shift in how you’re working and what you’re achieving today in your career? Let’s make that happen for you!
In my 6-session Career & Leadership Breakthrough 1:1 coaching program, I help professionals create and achieve what they want most, which includes more confidence, impact, advancement, financial reward, and fulfillment.
I’ve worked with over 20,000 professionals across 6 continents, and before that, I served as a therapist, and before that, I was a corporate VP, managing multi-million dollar budgets and global initiatives.
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!