This as-told-to story is based on a conversation with Jenny Wood, a former Google executive who is the author of the newsletter Big Small Things and forthcoming book Wild Courage: Go After What You Want and Get It. At Google, Wood led a large operations team that helped drive billions of dollars in revenue per year and started a passion project within the company called Own Your Career, which grew into one of the largest career development programs in Google’s history. Wood lives in Boulder, Colorado with her two young children and her husband, Jon.
Image Credit: Tim Gillies. Jenny Wood.
I moved to New York in 2008, and I was on a mission to meet my husband. I was so excited to move from Denver to New York because there are a lot more people in New York, and I figured I was widening my prospects. At one point — and my sister talked about this in her speech at my wedding — I went on five dates in 24 hours.
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I was so driven and operational in my approach that I kept a spreadsheet tracking these first dates. The columns were: name, age, height, date of first contact, summary of our online conversation and if the date was set. On a scale of one to three, is he funny? What’s my excitement level? I was not messing around. But also, I was sad because I hadn’t found anybody, and I was 30. I’d probably been dating with too much left-brained tenacity — I tend to think with my head and not my heart.
Image Credit: Courtesy of Jenny Wood. A replica of the spreadsheet Wood used to track dates.
“My life changed on the crowded, stinky, dirty C line of the New York City subway.”
My life changed on the crowded, stinky, dirty C line of the New York City subway. It was January 11, 2011. I remember because it was my mom’s birthday. There was a blizzard, and I was riding the subway home from work after a rehearsal at Google. (I was in an a capella group called Scalability).
I’m sitting on the subway; it’s a packed train, and about 20 feet away from me stands this attractive guy. Gorgeous blue eyes. Perfectly coiffed five o’clock shadow. The whole works. Even though I wanted to approach him, I talked myself out of it. What if he’s a convicted felon? What if he’s married? What if I make a fool of myself on this packed train while 100 people watch? Later, I realized these are three classic fears that hold so many people back: fear of uncertainty, fear of failure and fear of judgment.
I sit and do nothing as the subway passes stop after stop. I’m a bold and confident Google leader on the outside but timid and scared on the inside. Yet I’m still drawn to him, and I make a deal with myself: If he gets off at my stop, 72nd Street, then I’ll talk to him. If not, then c’est la vie.
At 59th Street, he picks up his bag and exits the train. I slump down in my seat, thinking, Oh, this is so frustrating, but that’s the universe telling me it wasn’t meant to be. At that moment, this wave of wild courage washes over me and pushes me out of my subway seat and toward those closing subway doors. No, screw the universe. I run off that train and think, I’m going to make my own damn “meant to be.”
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“With zero plan, I tap him on the shoulder as he exits the stairs of Columbus Circle.”
I chase after him, all disheveled in my winter coat, and take my hat off — my hair is a mess. With zero plan, I tap him on the shoulder as he exits the stairs of Columbus Circle, and I say, “Excuse me, I’m sorry to bother you.” “That’s okay. You seem nice,” he says. And I 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 thought you were cute. Any chance I could give you my business card?”
It seems like it takes forever for him to respond, but he takes the card.
We went on our first date at Dive 75 on 75th and Columbus on the Upper West Side. I knew immediately that I wanted to marry this guy. We sat in these heavy leather chairs with arms that created some distance, so when he went to the bar to get us beers, I pulled the chairs closer. That’s how giddy I was. My heart was pounding.
We dated for three years, got married and now have two kids, who are 7 and 9.
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“Feeling that wave of wild courage on the subway changed my life.”
Feeling that wave of wild courage on the subway changed my life. It inspired me to grow to be an executive at Google, to build a career program at Google that was used by tens of thousands of people in almost 100 countries and to write my forthcoming book Wild Courage: Go After What You Want and Get It. That wild courage tapped into my right brain, not my left brain. It inspired me to go with my gut, throw caution to the wind and take a calculated risk that set my entire life up for success.
Image Credit: Courtesy of Penguin Random House
From that moment, I made a mental switch, and so much started happening. I started asking for what I wanted at work. I got promoted. I grew from entry-level to executive, eventually helping drive billions of dollars in annual revenue for Google. People were impressed with my rise and would come to me for mentorship. Sometimes, mentees would ask how I rose to my leadership position at Google, so I started a program called Own Your Career — a no-nonsense approach to getting ahead professionally.
Mind you, I’d never worked a day in HR or people operations. For years, I was essentially the COO of various divisions of Google. I’ve done everything that Fortune 500 execs do. I’ve hired and fired people, reorged large divisions, shut down business units in one part of the world and built them up in another and delivered double-digit revenue growth — but I’d never given official career advice. That was not what Google paid me to do. Nonetheless, I wrote down tips and assembled a training, expecting a dozen people to show up. The program blew up, becoming one of Google’s largest career programs in the company’s 26-year history.
I realized I loved coaching people to be better than they think they can be. Fast-forward a few years, and the wild courage habit continued to serve me: I convinced a top literary agent to sign me. I set out to help not just tech employees but millions of people worldwide. So, I wrote the book proposal that would become Wild Courage. Wild courage is about how to get what you want in life, whether it’s a relationship, goal or promotion. A big part of it focuses on the nine traits you need to embrace to get there. The chapter titles are “Weird,” “Selfish,” “Shameless,” “Obsessed,” “Nosy,” “Manipulative,” “Brutal,” “Reckless” and “Bossy.” It’s about reclaiming these labels that create the bars of an invisible cage that keeps you small.
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“Don’t let fear shape your decisions.”
I reclaimed those traits on the subway that day, and I stopped living in fear: the fear of someone labeling me one of these traits, as well as the fear of uncertainty and failure.
Don’t let fear shape your decisions. How often do you avoid something because you’re scared of what might happen? How often do you put off asking a client for what you need? How often do you not ask your partner for what you want? How often do you not give your phone number to an attractive person on the subway? I want people to realize that it’s not a lack of money, skill or connections that get in your way — it’s you. And that’s good news because it means you have agency and control over your actions. When you can push past fear, you can accomplish so much.
You will never feel as purposeful, powerful or alive as when you’re pushing past that fear to success on the other side — because everything you’ve wanted lives on the other side of fear, and it’s right there waiting for you.
Preorder Wild Courage: Go After What You Want and Get It here.
Sign up for Wood’s weekly newsletter here.
