Wild Courage Book Summary: How to Overcome Fear and Get What You Want (Jenny Wood’s Key Takeaways)

By Hemanta Sundaray

PostedJune 22, 2025

Have you ever wanted something—a promotion, a date, a new life path—but hesitated? A quiet voice of doubt held you back, whispering "what if?" What if you fail? What if people judge you? What if you make a fool of yourself?

Former Google executive Jenny Wood argues that bridging the gap between what you want and what you get requires one thing: wild courage.

In her bestselling book, Wild Courage: Go After What You Want and Get It, Wood provides a practical, no-nonsense guide to smashing through fear and embracing your ambition. This post provides a summary of the core ideas from Wild Courage, based on an incredible talk Jenny Wood gave at Google.

What is Wild Courage? A Lesson from the NYC Subway

Jenny Wood’s entire life changed on a crowded subway train. She spotted a handsome man, but her mind instantly filled with doubts. "What if he's a convicted felon? What if he's married? What if a hundred people stare at me?" These questions, she realized, were masks for the three universal fears that hold us all back:

• Fear of Uncertainty
• Fear of Failure
• Fear of Judgment

She almost let the moment pass. But as the man got off at his stop, a wave of "wild courage" pushed her out of her seat. She chased him down and gave him her business card. That man, John, became her husband.

This story perfectly captures the essence of her book. As the New York Times article about their meeting was titled "Serendipity 1, Spreadsheet 0," Jenny maintains a different view. She believes serendipity isn't found, it's made. Wild courage is the habit of making your own luck by taking action despite your fear.

The 9 "Negative" Traits of Bold and Successful Leaders

At the heart of Wild Courage is a revolutionary idea: the very labels you fear are the keys to your success. Wood identifies nine traits that often form an "invisible cage that keep you small." We worry people will call us these things if we're too bold.

But what if we reclaimed them? When used in a sane and savvy way, these traits can supercharge your career. The nine traits of wild courage are:

• Weird
• Selfish
• Shameless
• Obsessed
• Nosy
• Manipulative
• Brutal
• Reckless
• Bossy

A Deep Dive into 3 Actionable Wild Courage Traits

In her talk, Jenny Wood offered a closer look at three of these traits, providing stories and practical tools. This section serves as a mini Wild Courage review, showcasing the book's actionable wisdom.

1. Bossy: The Courage to Lead Through Listening

When we hear "bossy," we imagine someone barking orders. Wood redefines it as the courage to steer others to success through collaboration.

She learned this the hard way. Early in a senior leadership role and riddled with imposter syndrome, she created a 30-slide deck outlining a full strategy for her new team before their first meeting. She walked in, presented her plan, and the energy in the room died. Her team felt insulted. "Why wouldn't you call on our expertise before deciding on the strategy?" they asked.

Mortified, she scrapped the plan and spent the day co-creating a new one with them. The lesson?

This is backed by a psychological principle called the IKEA Effect: we value things more when we have a hand in building them. A truly "bossy" leader doesn't have all the answers; they have the courage to listen and build the plan with their team.

2. Brutal: The Courage to Protect Your Priorities

Being brutal isn't about being unkind. It's about being ruthless in protecting your time, energy, and what truly matters. It's the courage to draw firm lines and say "no."

Wood shares a gut-wrenching story about being on a work trip in New York when her five-year-old daughter, Noah, had an accident at her in-laws' house. Noah’s hair got caught in a kitchen mixer, tearing a patch from her scalp. On the phone, her daughter was sobbing, begging her to come.

Jenny hesitated. She looked at her packed calendar—meetings with her team, her manager, colleagues who flew in from India. She rationalized that Noah would be fine and decided to stick to her work agenda. Two days later, she saw her daughter in person and the reality hit her. The missing patch of hair was so much worse than she had imagined.

"All I had to do was say no to my work agenda and say yes to my daughter," she reflects. "I failed to muster the wild courage to enforce my boundaries."

The lesson is a question we all must ask: How do you vote with your calendar? Sometimes, the bravest thing you can do is be brutal with your schedule to say yes to what is truly important.

3. Obsessed: The Courage to Set Your Own Standard

Forget the negative image of obsession. Wood reframes it as a deep, enthusiastic drive to push, perform, and persist. An obsession with excellence fuels your effort and career. Here are four practical tools she shared to channel this trait:

• The Monday Minifesto: Don't just report on tasks. Send a brief weekly email to your manager outlining two things you were proud of last week and two you're excited about for the coming week. This showcases your value and helps your manager advocate for you.
• Pull It and Bullet: When writing an important email, pull 50% of the text and rewrite it in bullets. This forces clear, succinct communication, making it easy for busy stakeholders to grasp your point and increasing your influence.
• Tame the Octopus: To avoid rambling in meetings, take a pause before you speak. Identify three key points, state them upfront ("My thoughts fall into three areas: priorities, tools, and alignment"), briefly explain each, and then summarize them again at the end. This makes you sound poised, confident, and clear.
• Woo with You: When trying to persuade someone, shift the focus from "I" to "you." Review your emails and flip sentences to start with "You" instead of "I." For example, instead of "I want to follow up on our meeting," try "You mentioned an interest in..." This honors the other person and builds stronger alliances.

Your First Step Towards Wild Courage

How often do you let fear shape your decisions? Wood closes with a story about her Grandma Lyla, a CEO until age 92, whose motto was:

When Jenny's husband was laid off, Grandma Lyla told him to get his ego out of the way and find a compromise. He went back to his VP, offered to work 10% of the time for 10% pay while he job hunted, and they accepted. He got to keep his job title while searching, and the company got to keep his expertise.

This is the spirit of Wild Courage. It’s about not taking no for an answer, especially from the fear inside your own head.

Whether you start by sending a Monday Minifesto or simply striking up a conversation with a stranger on a train, the message is clear: everything you've ever wanted is waiting for you on the other side of fear.

What's one small act of wild courage you will take this week?