Jenny Wood spent 18 years at Google climbing the ranks from entry-level to executive, most recently running a large operations team that helps drive billions in revenue per year. She also created one of Google’s largest career programs ever, loved by tens of thousands of employees worldwide. Now, as a speaker and author, she shatters conventional wisdom about personal and professional advancement.
What’s the big idea?
Conventional career wisdom has warped important traits into bad words. Shameless, manipulative, selfish—these are only a few of the maligned terms that describe indispensable qualities of ambitious people. Many talented people stay stuck because they are scared, but pushing through fear can invigorate a career.
Below, Jenny shares five key insights from her new book, Wild Courage: Go After What You Want and Get It. Listen to the audio version—read by Jenny herself—in the Next Big Idea App.
1. Get uncomfortable.
It’s 2011, and I’m riding the crowded, dirty C train home from work when, 20 feet away, stands this gorgeous guy. Blue eyes, thick wavy hair, the works. But there are no social norms around talking to people on the subway. You just don’t. I made a deal with myself: if he gets off at my stop (72nd Street), I’ll say hi. If not, c’est la vie.
He gets off at 59th Street.
That should have been the end of the story. But something inside me shifts. A wave of wild courage washes over me, and I leap through the closing subway doors. I chase him down, tap him on the shoulder, and say, “You’re wearing gloves, so I can’t tell if you’re wearing a wedding ring, but if you’re not married, you were on my subway, and I think you’re cute. Can I give you my business card?”
As he says nothing, I convince myself this was a bad idea.
Then…finally, he takes my card.
That moment of wild courage changed my life. That stranger became my husband. Jon and I have been married 11 years and have two kids. The New York Times wrote about our story and it went viral—because people want permission to have wild courage.
So many brilliant people stay stuck, following outdated advice like:
- “Don’t rock the boat”
- “Your work will speak for itself.”
- “Wait your turn.”
I used to believe in those things, too. In my time at Google, I conjured up plenty of fear:
- Fear that I wouldn’t impress my boss in our weekly one-on-one.
- Fear that I would say something stupid in that big meeting full of VIPs.
- Fear that no one would ever forget that presentation I flubbed.
I was “cool and collected” on the outside, but a lot more was going on inside. Fear will always be my companion. I have succeeded largely by pushing through fear to achieve my heartfelt ambitions. All ambitions hide on the other side of fear.
And that’s exactly what led me to question everything I’ve been taught about success. What if the traits you need to get ahead are the opposite of what you’ve been told? Wild Courage is not just another professional development book—it’s a rebellion against conventional career wisdom.
Wild courage is about embracing the traits that make people uncomfortable—the very ones that actually lead to professional and personal breakthroughs. Those traits are:
1. Weird
2. Selfish
3. Shameless
4. Obsessed
5. Nosy
6. Manipulative
7. Brutal
8. Reckless
9. Bossy
These traits helped me climb to senior leadership at Google. But more importantly, they helped me get seen, get heard, and get ahead. I want to help YOU do the same.
2. Get shameless.
Shamelessness is a survival skill. For a brief period early in our marriage, Jon and I stayed on my Grandma Lila’s pullout couch while apartment hunting.
Before I go any further, you should know that my grandma is no ordinary grandmother. She retired as CEO of a financial services firm at age 92. At four-foot-ten and 90 pounds, she was unstoppable. She had no shame about going after what she wanted.
Well, Jon comes home from work one day and, over dinner, reveals that he’s been part of a major layoff. I’m crushed. But as I look across the table, Grandma Lila has a gleam in her eye.
“No is just an opening offer,” she says. While most people would be too embarrassed to challenge a layoff, Grandma didn’t care about looking desperate or inappropriate. “Don’t sign the paperwork.”
“Shamelessness is a survival skill.”
Jon and I exchange glances, trying to figure out how to delicately communicate what we are thinking. Finally, Jon sighs and says, “I don’t think it works that way. A layoff is a one-sided thing. They say, ‘You don’t work here anymore.’ I say, ‘OK.'”
But Grandma Lila persists. “Sure, taking no for an answer would be more comfortable, but the discomfort will pass. Get your ego out of the way and find a compromise. What’s the worst that could happen? They’ve already let you go.”
Finally, Jon relents. He calls his company the next day and halfheartedly proposes staying on at 10 percent time and pay while job hunting. To his surprise, they accept.
I’m not sharing this story as an influence tactic per se. Candidly, I think Jon got lucky that they said yes. The point is Grandma Lila’s lesson: don’t let fear shape your decisions.
Personal and professional growth demands having the courage to stand behind your efforts and abilities, even when others might judge you. Being shameless isn’t about being inappropriate. It’s about having the courage to advocate for yourself when others would stay quiet. When your career and livelihood are on the line, shame is a luxury you can’t afford.
Here is a practical tool: the shameless Monday email. Every Monday, send your manager a brief email with two things you are proud of from last week and two priorities for this week. Be specific (use numbers if you can) and deliberately use the word “proud.” You worked hard, so own it! For example: “I’m proud we launched the new feature five days ahead of schedule” is much stronger than “Made progress on the project.” This builds your visibility while documenting your wins.
3. Get manipulative (in a good way).
“Manipulative” sounds like a dirty word. But what if we could reclaim it? Think about a lump of clay. When an artist manipulates it, they create something beautiful and innovative. Great leaders do the same thing. They shape opportunities, build creative teams, and influence through empathy and connection.
When I wanted to meet Vanessa Van Edwards, the famous author, I didn’t just hope for luck. I strategically changed my flight to create what seemed like a serendipitous airport meeting. Was it manipulative? Perhaps. But it led to a valuable mentorship and friendship that benefited us both. For what it’s worth, I fessed up about the flight change once Vanessa and I got to know each other better. A seeker of influence herself, she found it hilarious.
Influence is not about tricking people. It’s about understanding what others want and need. Three Duke professors demonstrated this brilliantly in their study of what they called “the IKEA effect.” They divided people into two groups: one received a pre-assembled IKEA box, and the other had to build it themselves. When asked to price their box for resale, those who assembled their own box valued it 63 percent higher. They had a higher sense of the item’s value because people need to weigh in to buy in. Being part of the creation, they valued the work more.
“Influence is not about tricking people.It’s about understanding what others want and need.”
When used ethically, being manipulative means having the courage to win people over by understanding their needs and motivations. It’s about warming the room with positive energy and connecting with others on a human level. Nobody cares how much you know until they know how much you care.
Here is a practical tool: woo with “you.” The next time you write an email to someone senior or important, count how many sentences start with “I.” Then, rewrite it focusing on your recipient. Instead of, “I loved working with you on the success of this project,” try, “You made this project successful.” Make the recipient the hero, and you both win. This simple shift engages their attention and changes their attitude.
4. Get selfish.
The best leaders are selfish about their priorities, productivity, and focus. When is the last time you saw someone praised in a performance review for being selfish? Of course not. We’ve been conditioned to see selfishness as a character flaw: The person who shoves everyone else out of the way to get ahead.
But after nearly two decades as a tech executive, I saw the opposite problem: exceptionally talented people staying stuck because they were too selfless. They were the ones who never rose to leadership positions because they:
- Let others take credit for their smart ideas.
- Said yes to every favor asked of them.
- Put everyone else’s priorities ahead of their own.
When you give everyone else a leg up at your expense, you will get trampled. Savor the word “selfish.” It helps you spot that insidious guilt around doing things for yourself:
- Skipping a meeting to get focused work done.
- Declining to stay late for work that will have the same urgency tomorrow.
- Having your spouse handle both kids on a flight so you can prepare for your presentation.
When someone asks, “Hey, do you have 30 minutes to look over this proposal?” or “Can you hop on a quick call?” your instinct might be to say, “Sure, no problem.” But yes—problem! Every time you say yes to someone else’s priorities, you say no to your own. Being agreeable invites more responsibility but not more authority.
Being selfish isn’t about disregarding others, it’s about having the courage to stand up for what you want. After all, if you don’t advocate for yourself, who will?
“You can’t lead others if you’re constantly depleted from saying yes to everyone else’s priorities.”
The most effective leaders understand this balance. They’re selfish about their time and energy precisely so they can be more generous with their impact. You can’t lead others if you’re constantly depleted from saying yes to everyone else’s priorities.
Here is a practical tool: say yes to the big, no to the small. Learn to spot NAP work, meaning “Not Actually Promotable.” Being the 18th person to reply “Happy Birthday!” on a thread? NAP. Attending meetings you don’t need to? NAP. Planning the company picnic. NAP. Instead, focus your energy on what moves the business forward: increasing revenue, shortening time to market, and improving customer satisfaction. These are the tasks that get you promoted. Leaders praise can-do attitudes but don’t promote can-doers who do nothing big. Don’t nap at work.
5. Get ahead by pushing past your fear.
How often do you not do something because you fear what might happen? How often do you not ask for the promotion? How often do you not take a risk, like giving the cute person on the subway your number?
When we don’t take action, chances are it’s because of fear:
- Fear of uncertainty.
- Fear of failure.
- Fear of judgment.
- Fear we might be called shameless, manipulative, selfish, or one of the other nine traits.
When fear is the blocker, that’s incredible news, because we can push through fear. Muster the wild courage to chase what you want, and you’ll discover a vital truth: whether you succeed or fail at any one thing, you will never feel as purposeful, powerful, and alive as when you’re pushing through fear toward the wonder and joy on the other side. Everything you’ve ever wanted is waiting for you on the other side of fear.
To listen to the audio version read by author Jenny Wood, download the Next Big Idea App today:
