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The Art of Manliness

How to Turn Vices Into Career-Advancing Virtues

The Art of Manliness

The Art of Manliness

Society & Culture, Education, Philosophy

4.714.5K Ratings

🗓️ 17 June 2025

⏱️ 54 minutes

🧾️ Download transcript

Summary

What if the traits you’ve been taught to suppress your entire career are actually the very qualities that separate those who get what they want from those who stay stuck waiting for recognition that never comes? Today on the show, Jenny Wood argues that most of us are living in what she calls “an invisible cage” created by an overabundance of caution, and that the biggest lie you’ve been told in your career is to keep your head down and let your work speak for itself. Jenny is a former Google executive who developed a career development program used by 56,000 people in nearly 100 countries, and she’s the author of Wild Courage: Go After What You Want and Get It. In our conversation, Jenny explains how traits that have a negative rap can be used for positive ends that will advance your career. We discuss how being shameless, reckless, nosy, manipulative, obsessed, and more can help you overcome your success-hindering fears, take bolder action, and achieve your goals.

Transcript

Click on a timestamp to play from that location

0:00.0

Brett McKay here and welcome to another edition of the Art of Manliness podcast.

0:11.5

What if the traits you've been taught to suppress your entire career

0:14.1

or actually the very qualities that separate those who get what they want

0:17.2

from those who stay stuck waiting for recognition that never comes?

0:21.1

Tate in the show, Jenny Wood argues that most of us are living in what she calls an invisible

0:24.8

cage created by an overabundance of caution, and that the biggest lie you've been told in your

0:29.1

career is to keep your head down and let your work speak for itself.

0:32.9

Ginny is a former Google executive who developed a career development program used by

0:36.2

56,000 people in nearly 100

0:38.1

countries. And she's the author of Wild Courage. Go after what you want and get it. In our conversation,

0:44.4

Ginny explains how traits that have a negative rap can be used for positive ends that will advance your

0:48.3

career. We discuss how being shameless, reckless, nosy, manipulative, obsessed, and more help you overcome your success-hindering

0:56.2

fears, take bolder action, and achieve your goals. After shows over, check out our show notes at

1:01.1

a.com. IS slash wild courage. All right, Jenny Wood, welcome to the show.

1:19.8

Thanks so much for having me, Brett.

1:21.5

So you were a successful Google executive.

1:24.7

While you were there, you also developed a career development program

1:28.1

that helped employees advance their careers by learning how to advocate for themselves,

1:33.4

stand out for the crowd. So you've made a career for yourself by being unapologetically ambitious,

1:38.8

like going after what you want. Have you always been like that? Were you like that as a kid?

1:42.6

Or was there a moment in adulthood where that switch finally flipped? And you're like, all right, I'm going to start turning my ambition into action?

1:49.9

Ooh, there was a moment, Brett. There was a moment. And it was in 2011 on the New York City subway when I was riding the subway home from work and about 20 feet away from me stands this really good looking guy.

...

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