Wild Courage: Go After What You Want and Get It

By Jenny Wood

INSTANT NEW YORK TIMES BESTSELLER

A bold, empowering, and energizing guide to embracing your ambition and chasing after what you want from an executive who spent nearly two decades climbing the ranks at Google.

"Extraordinary." -Kim Scott

"It's about pushing past fear and daring to be yourself." -Dan Pink

What if the traits you need to get ahead are the exact opposite of what you’ve been told?

To be successful you need to be Weird, Selfish, Shameless, Obsessed, Nosy, Manipulative, Brutal, Reckless, and Bossy. And that takes courage.

As a former Google leader and top career coach who chased an attractive stranger off the subway and later married him, Jenny Wood knows her way around courage. In this book, Wood shatters conventional wisdom about achieving your goals. She gives you permission to ditch your fear and chase after what you want, unapologetically.  

Wood reclaims nine traits from their negative shackles and teaches you how to apply them in a savvy and sane way to supercharge your success, whether you’re trying to impress your new boss, snag a stretch promotion, or land a life-changing deal.

Wild Courage will teach you how to be:

Weird: Win as you or lose as “who?”
Selfish: Be your own champion.
Shameless: Kick impostor syndrome to the curb and self-promote with ease.
Obsessed: Push, persist, and perform at your highest level.
Nosy: Get curious to network confidently and learn from others.
Manipulative: Build influence with empathy and manage up like a pro.
Brutal: Draw lines and stick to them. Embrace the power of no.
Reckless: Err on the side of action and take healthy risks.
Bossy: Steer others to success, even if you’re not in charge yet.

Wild Courage coaches you to smash through your fear of discomfort, failure, and the judgement of others, to embrace your boldest self in pursuit of what you want. To be successful, you need to have courage. Wild amounts of it.

• Language: English
• Publisher: Penguin Publishing Group
• Release date: Mar 25, 2025
• ISBN: 9780593717653

Jenny Wood

Jenny Wood is an unstoppable confidence booster dedicated to helping people make their impossible dreams come true. After chasing an attractive stranger off the subway, giving him her number and later marrying him, Wood vowed to always pluck up the courage to go after what she wanted in life. And it’s worked; Wood is a Google Executive, founder of Own Your Career, speaker, writer, mom and pilot. Her writing has been featured in Harvard Business Review, Entrepreneur, Inc. and Forbes. She earned her B.A. in Economics & International Business at Brandeis and was a research associate at Harvard Business School. She lives in Boulder with her husband and their two kids. Wild Courage is her first book.

Book preview

1

Weird

Win as you or lose as who?

Weird

(adj.): of strange or extraordinary character.

Weird redefined: The courage to stand out.

Before catching the right man on the New York City subway, I embarked on a painful, long-drawn-out chase after the wrong one: Brian. Instead of moving on when the wrongness of the match became obvious—to any rational person, anyway—I refused to accept defeat. By the time I stopped twisting my authentic weirdness into his idea of normal, I’d done real damage to myself.

Never again.

There is no normal. We’re all Weird in different ways. I’m bold, outspoken, driven, confident, and a bit loud. I dance down the sidewalk in public while listening to a cappella Broadway show tunes on my headphones. I’ve never been one to play it cool, dim my light, or curb my enthusiasm, and some people find me odd or a bit much.

My attributes have always been strengths or weaknesses, depending on the context and how well I’ve leveraged them. Unfortunately, with Brian, my iron determination quickly became a weakness. From the start, he wanted someone demure and quiet. A wallflower. More accurately, a blond and petite wallflower. Ignoring this disconnect, I pursued him, and eventually, we started dating. Sort of.

I want to be with someone gorgeous but insecure, Brian once told me. Someone who doesn’t realize how pretty she is. How do you respond when someone you’re supposedly dating says that? However, as embarrassing as it is to admit, Brian’s distancing behavior drove me to continue chasing him. The more he pulled back, the more I leaned in, becoming less myself while getting no closer to becoming the person he really wanted.

Short of dyeing my hair blond, I did everything I reasonably could to fit Brian’s specifications: I behaved demurely, spoke quietly, and even dressed differently. When Brian suggested I wear tighter jeans, my heart sank. But I bought the jeans anyway.

It took six full years of flirtation, dating, friends with benefits, and "what even is this?" conversations to hit bottom. While I was squatting in the rubble of my old self, it finally struck me: I would never be Brian’s person. Mustering the courage, I made a clean break. (See Brutal for more on those.) One of the best decisions I’ve made, however late. If you keep squeezing your square peg into a round hole, you’ll get bent out of shape.

Brian has wonderful qualities. To this day, I think of him fondly. My Weird just wasn’t compatible with his. In retrospect, my reluctance to abandon pursuit drove some of his questionable behavior. I needed someone who wanted me as I was. Learning to own my Weird instead of repressing it rescued me from endless heartbreak and set me on the path toward finding the love of my life. Embracing my authentic self also elevated my other personal and professional relationships, improving my life and accelerating my career.

Are you ready to own your Weird?

In defense of being a little weird

After World War II ended, US fighter pilot casualties kept rising. The air force suspected the cockpit design. Pilots were struggling to reach the controls while maneuvering, with disastrous consequences. What was happening? Why didn’t cockpits fit their pilots anymore?

Had the average pilot gotten larger since the 1920s? After all, the American diet had become more abundant. To his surprise, Gilbert S. Daniels, the Harvard-educated lieutenant assigned to solving the problem, discovered that the average pilot didn’t exist in the first place. Cockpits had been designed around average measurements—average height, average arm width, and so on. However, no air force pilot was within 15 percent of the average on all ten body measurements. Like the American family with 2.5 kids, the average pilot around whom cockpits had been designed was a statistical mirage. Every pilot was Weird.

The aircraft controls had never been easy to reach. Accidents happened more frequently because planes had gotten faster and their controls more complicated. With less time and more complexity, that extra half an inch required to hit a button or flip a switch went from annoyance to deadly hazard.

Once Daniels convinced the top brass that every pilot was unique (i.e., Weird), the air force introduced adjustable seats, and the accident rate plummeted.

(There’s still room for improvement today. As a five-feet-four-inch private pilot, I sit on three cockpit cushions to see over the nose of the plane.)

Within your Weird lie your greatest strengths. Unfortunately, parents and teachers try to buff out these quirks. If you have young kids, you probably do the same thing, consciously or not. Teaching kids to fit in is a protective instinct that long ago helped humans survive in small tribes. As adults, we must rediscover our rough edges. To stand out and thrive, hone and highlight every ounce of Weird you’ve got. All that talk in the corporate world about personal branding? Forget hiring a graphic designer to pick cool fonts for your website or a consultant to tweak your LinkedIn profile. Building a personal brand means revealing what makes you distinct.

Carlye Kosiak was one of our best hires at Google. After rising through the ranks, Carlye is now a global product lead. Did I choose to interview her because of the remarkable accomplishments on her résumé? Accomplishments are table stakes at a company like Google. No, I interviewed Carlye because, besides her impressive work history, her résumé indicated an interest in recipe tasting in pursuit of the perfect oatmeal raisin cookie. Carlye had the chops to work at Google, but so did fifty other CVs in my stack. She got the interview because her résumé featured a pop of personality the other résumés lacked. In only ten words, Carlye conveyed Weird (a personal revelation that I wouldn’t have known otherwise), Reckless (taking a risk with the quirky addition that wasn’t strictly necessary), Nosy (curiosity to learn about baking), and Obsessed (pursuing perfection in oatmeal raisin cookies). Talk about efficient communication (Brutal)!

Don’t run off to add hobbies to your résumé just yet. Being Weird isn’t about saying something wacky to catch a hiring manager’s attention. It’s about being yourself and revealing that self appropriately, both in your résumé and everywhere else. While many people list hobbies on résumés, Carlye didn’t write foodie on hers. She revealed something specific, fun, and creative about herself. And that was only part of it. Carlye landed the job because the candidate I met matched the colorful clues in her résumé. It wasn’t a tactic. It was her. Authenticity won the role.

To stand out, let it hang out…within reason. Figuring out who you are—how you think and solve problems, what you enjoy and dislike, the values that matter most—is essential in (a) deciding what to chase in life and (b) actually catching it. Aiming for average always feels safe, but the results are boring and forgettable. Being forgotten is the real danger in any career. Life is too busy and competitive on this crazy planet for well-rounded to make a dent. Get angular.

Put yourself in the other person’s shoes. When someone plays it cool in a job interview or on a first date, you know you’re seeing the mask, not the person. The irony is that we crave reality in others yet project a fantasy about ourselves to others. Especially on social media. Then, we wonder why no one pays attention.

Risk authenticity or ensure anonymity.

New Google employees—Nooglers—discover that exceptional is expected at the company. These big fish find themselves in an even bigger pond where diligence, intelligence, and competence are par for the course. If they don’t make a splash, they sink without a trace.

Think about that intern who worked in your department last summer. They played it safe. Rather than rock the boat, they formatted their résumé according to the guidelines, arrived promptly in the expected business casual attire, and quietly observed every meeting. Where are they now? And what was their name again?

Follow the rules and meet expectations. Pay your taxes and sign on the dotted line. But remember that the unwritten rules we obediently follow to fit in aren’t rules at all. They’re traps, filters to weed out people without the guts to transcend them. Study the careers of notable figures in business, science, politics, or the arts. Breaking with convention is the only rule they consistently follow.

We interpret unconventional behavior as a sign of unusual talent. Jason Feifer, editor in chief of Entrepreneur magazine, pointed me to an eye-opening study by researchers at Harvard identifying the red sneakers effect: we perceive people who dress unusually—wearing red sneakers to a formal event, for example—as higher in status. Because breaking with conventions can theoretically get you in trouble, it follows that someone choosing not to conform must be powerful enough to get away with it.

To be clear, it has to be done with thoughtfulness and intention. Wearing a wrinkled suit that doesn’t fit properly looks accidental. Pairing bright red sneakers with an elegant tux at a black-tie event is obviously a choice. The choices can be meaningful: Nonconforming behaviors, the researchers write, as costly and visible signals, can…lead to positive inferences of status and competence in the eyes of others. In other words, when someone deliberately breaks the unwritten rules of behavior in a given context, we usually assume they’re good enough to get away with it.

It’s called a power move for a reason.

As with every Trait in this book, there are right and wrong ways to approach Weird. For example, wearing a black T-shirt to a Michelin-starred restaurant won’t convince the maître d’ that you’re a rock star. Yes, this is the kind of thing rock stars do, but always together with other subtle, contextual details you’ll never effectively mimic. If nonconformity signals status, clumsy imitation signals the opposite. We know the real thing when we see it. Stick to what you know and who you are: it’s Weird enough.

According to research, authenticity drives work outcomes such as job satisfaction, in-role performance, and work engagement. But being yourself isn’t just a good strategy for getting ahead. It’s good for you. Struggling to meet some imagined template—cool, hip, leadership material—leaves you feeling alienated and sad. Instead, get comfortable with the discomfort of being yourself. Stop suppressing every impulse and instinct. This liberates enormous mental and emotional energy you can invest in going after what you want. For example, my team at Google was once up for an award we really wanted to win. Rather than fill out the submission form with dry details about our project and its business impact, we spent way too much time making a goofy music video. Talk about