Stop playing it safe—embrace the bold, unexpected traits that actually get you ahead.

Success doesn’t come to those who wait—it comes to those who take it. For years, you’ve been told to be humble, play nice, and wait your turn. Jenny Wood says that’s exactly why so many talented people stay stuck. As a former Google executive turned author of Wild Courage: Go After What You Want and Get It, she’s here to expose the real traits that drive success—ones that might make you uncomfortable. Forget the polite career playbook, being selfish, obsessed, even a little manipulative (the right way) can actually be your biggest advantage. Jenny gets radically candid with Kim and Amy on why risk-taking beats waiting for permission, why saying “no” is a career superpower, and how to self-promote without sounding like a jerk. If you’re sick of playing it safe and watching others pass you by, this episode is your permission slip to take bigger swings and get what you want.

Get all of the show notes at RadicalCandor.com/podcast.

Episode Links:

• Wild Courage by Jenny Wood
• The Story of “How About Never” | The New Yorker
• Newsletter | Jenny Wood
• Watch on YouTube

Connect:

• Website
• Instagram
• TikTok
• LinkedIn
• Facebook
• YouTube

Chapters:

(00:00:00) Introduction
Kim and Amy welcome Jenny Wood, author of Wild Courage: Go After What You Want and Get It.

(00:1:02) The Nine Traits That Will Get You Ahead
Nine controversial traits that are actually career superpowers.

(00:4:26) The Subway Story That Changed Everything
Jenny shares a story on ignoring self-doubt and taking action.

(00:10:16) Calculated Risks vs. Playing It Safe
Why taking smart risks is essential for personal and professional success.

(00:13:04) The Google Factor: How It Shaped Wild Courage
How Google built confidence, encouraged risks, and sparked creativity.

(00:17:09) Owning Your Weird
Advice for staying authentic in workplaces that don’t naturally foster it.

(00:21:38) Identifying Your Power Assets
Identifying your power assets to make self-promotion feel natural.

(00:25:22) Managing Up, Higher, and Diagonally
A tactical guide to workplace influence through strategic senior connections.

(00:31:54) Overcoming Bias in the Workplace
Strategies to counter workplace biases in recognition and self-promotion.

(00:36:56) Why Saying No is a Superpower
How learning to say no without guilt protects your time and energy. 

(00:42:40) Get in Front of the Right People
The importance of standing out and getting noticed by leadership.

(00:44:57) Pull It and Bullet It
The “Pull It and Bullet It” method for impactful, time-saving emails.

(00:48:05) Where to Find Jenny Wood
Where to get Wild Courage and find Jenny for keynotes and workshops.

(00:49:41) Conclusion