What’s Stopping You From Taking the Risk That Could Change Everything?

The Chase Jarvis LIVE Show

Chase Jarvis

Celebrity, Art, Career, Creativity, Money, Entrepreneurship, Self-improvement, Education, Careers, Writing, Interview, Investment, Influencer, Business, Photography

4.8 • 641 Ratings

🗓️ 26 March 2025

⏱️ 57 minutes

🔗️ Recording | iTunes | RSS

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Summary

In this episode, Jenny Wood shares how to overcome fear and take bold action.

Jenny spent 18 years rising from entry-level to executive at Google, where she founded one of the company’s largest career programs. Now, she’s the author of Wild Courage, a book that flips the script on success by reclaiming nine so-called “negative” traits—like being reckless, nosy, or shameless—and showing how they can fuel massive growth.

We get into what it really takes to break through fear, bounce back from rejection, and build the kind of courage that moves your life and career forward. Jenny holds nothing back—sharing wins, stumbles, and the surprising moment she chased her now-husband off a subway car.

Some highlights we explore:

The email rejection that made her lose sleep—and what she did next
Why separating “truths from tales” is a life-changing tool for fear
How to reframe being “shameless” as a leadership superpower
What it means to be obsessed... in the healthiest, most productive way

Enjoy!

Transcript

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0:00.0	Was there 18 years? Breadwinner for my family. Fancy executive salary. Very, very comfortable.
0:05.1	Never thought I would leave. But I was terrified to leave Google. Terrified. And so I would tell myself
0:10.9	all sorts of tales, right? Tales like, we're going to have to downsize. We're going to starve.
0:15.6	I will never be able to get hired again if the book flops because I'm 45 and, you know, no one's going to hire a 45 year
0:21.7	every single thing I just said is stuff that plagued me for a year. But they're all tales. So what are
0:28.2	the truths of this situation? I would likely make less money. I was leaving to write a book.
0:33.9	We had a lot in savings. My relationship to money is one thing, but, you know, there's other
0:38.3	values in life, like time with my family, being high net freedom. So once I was able to
0:43.1	separate the truths, which are verifiable facts, and when you can separate the truths from your
0:47.4	tales, that is what helps you push past the fear. This episode is brought to you by my Latest Book, Never Play It Safe.
0:59.3	Right now, if you do not have a copy of my latest book, I want you to listen to what Gary Vaynerchuk said about my latest book.
1:06.9	Building a life you love doesn't happen on accident.
1:09.9	It's a process.
1:12.4	Few people know this process like Chase Jarvis does and never play it safe is the roadmap. Or what Sophia Amaruso said.
1:19.9	This book is a powerful compass for embracing risk and creativity in all the aspects of your life.
1:26.2	Chase shows us how to step out of our comfort zones
1:28.3	and become who we were meant to be.
1:31.9	Here's a cool fact.
1:33.1	All of the best stuff in life is on the other side of your comfort zone.
1:38.3	And never play it safe is a blueprint.
1:40.8	That's how I designed it.
1:41.6	It's a blueprint to get you there reliably over and over
	...

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