One of the best compliments I ever got was from my friend Kristin Wong: “When I met you, I didn’t feel like I had to downplay the things I was ambitious about.”
If you looked at Kristin’s career, you’d never guess that she felt any discomfort around her own ambition — she’s a writer and journalist whose work has been published in places like The New York Times, ELLE and The Cut. She works as a writer and researcher at Hidden Brain Media, one of the most popular and prestigious podcasts on the planet (yes, those are my words, but they’re not an exaggeration). And receiving her newsletter is always a delight, (you can sign up here).
But Kristin is also my friend. And from that perspective, I’ve seen firsthand how success, no matter how impressive, doesn’t make you immune to self-doubt. So today, I’m excited to invite Kristin to Too Ambitious to share her own story of her relationship to ambition.
When I was 18, there was nothing I wanted more than a green Volkswagen Beetle. It was a car that represented everything I wanted to be: cute, quirky, hip. Yeah, maybe kind of weird — but mostly hip.
I did not, however, have new car money. I was still a high school student. A high school student who worked part-time at a greeting card shop where I earned $5.75 an hour. I was lucky if I could afford gas, much less buy a brand new, trendy German vehicle.
On my lunch breaks, I’d sit in the stock room with a peanut butter sandwich and a calculator, crunching the numbers to see how many more hours I would need to work to afford this car. I tried to think outside the box. Could I get a second job? Win the lottery? Was there a lucrative crime ring I could somehow infiltrate? The numbers never added up. “I don’t think it’s going to happen,” my mother said when she picked me up from work one day. “I know, but I have to try,” I told her. She laughed and said okay. I could tell we were both surprised by my stubbornness.
Everyone defines ambition a little bit differently, but this memory is how I’ve always thought of it. Ambition, to me, is when you want something enough that you’re willing to work hard for it — even when the outcome seems impossible. Even when the stakes are high, the cards are stacked against you, and there’s a good chance you’ll fail, you give yourself the opportunity to try.
Ambition also makes people deeply uncomfortable. Which is why, for better or worse, I’ve learned to keep my ambition to myself.
In November 2010, I was a fresh Los Angeles transplant eager to meet new people. So when a friend invited me to Thanksgiving, I said yes. As I hovered over the buffet table, my friend’s mom shuffled in next to me and asked why I had moved to L.A. I told her the truth: I wanted to be a writer. “Oh yeah? What do you want to write?” she asked. “I’d like to try my hand at screenwriting,” I said. After all, I was in Hollywood, why not give it a shot? She dumped a spoonful of mashed potatoes on her plate and replied, “Well, that’s ambitious.” Her response was drier than the cornbread stuffing. She walked away, and I nibbled on a biscuit, pretending not to feel naive and ashamed. I comforted myself with the fact that, despite the snark, she was right. I was ambitious. The sky is also blue.
The next day, walking down the streets of West Hollywood with a bag of groceries in hand, I found myself stewing on her words. I should have been enjoying the new city around me, bustling with writers and artists. Instead, I was replaying her comments in my head until it sounded more and more ridiculous, like a bratty cartoon character. ~WeLL tHaT’s aMbTtiOus~
She wasn’t the only person who took up space in my head. There was also the friend who offered unsolicited cynicism when I told him I was moving across the country. And the colleague who told me I’d come back to Texas with my tail between my legs.
Soon enough, my brain was buzzing with the words of anyone who ever doubted me. Walking back home, I thought, “I’ll do anything I can to make it here.” I had only been in Los Angeles for two months, and my ambition had morphed into something entirely different. It was no longer an act of generosity to myself — it was a way of proving other people wrong.
I spent the next year doing exactly that: applying to jobs I wasn’t crazy about, joining writing groups that didn’t feel right, forcing myself to network with folks who looked and behaved like the cast of Entourage. Eventually, I started freelancing as a scriptwriter while I worked for an entertainment news show during the day. Was it my dream to write snarky one-liners about Rihanna’s love life? No, but I was doing the thing that people said was too ambitious. You’re lucky to get any kind of job in Los Angeles, much less a writing job. It’s what I told myself every morning I dreaded waking up to go to work.
But on a Friday afternoon in spring, I had my Devil Wears Prada moment. The small entertainment company where I worked decided they wanted to launch a reality TV series. The show would follow the work and lives of the glitzy, celebrity-obsessed founders while the rest of us would play quirky supporting characters. A crew came to film us working, and the founders were encouraged to fight about something — who knows what — as a way of giving the episode a narrative arc. During this staged fight, the director wanted a reaction shot. He asked me to look toward the camera. “Let’s get a shot of you looking worried and confused,” he said. In retrospect, this should have been easy. But when I sat up, raised my eyebrows, and made my best dumb Chris Pratt face, everyone groaned. Not only was my reality TV debut unconvincing, it audibly repulsed the entire room. I tried to laugh it off and pretend that a little piece of myself hadn’t just died inside. But I wondered, What the hell am I doing here? It was like waking up on a car ride in the middle of nowhere.
How did I get here, and where was I going? I didn’t feel ambitious — I felt obsessive.
My career was no longer about reaching my own goals. I wasn’t even sure what those goals were anymore.
I was forcing myself to do something I didn’t want to do because of what other people might think.
I wish I could say I quit on the spot and found my dream job the next day. That would be a really satisfying story. And when I went home that weekend, I did start searching for something else. But more than a new job, I wanted to get reacquainted with myself, and that doesn’t usually happen in a single moment.
At least for me, reclaiming my ambition has been an ongoing process. It looks like creating boundaries — not saying yes to stuff just because I feel like I have to say yes to stuff. It looks like spending time with people who support me, and also understand me. It looks like getting more comfortable with speaking up and being honest with others. On the surface, these things might not seem to have anything to do with ambition, but if ambition is a way of taking yourself seriously, you have to know yourself to begin with.
People are so often afraid to say what they really want to do with their lives. And who can blame them? When you say out loud what you really want to do, it’s either too much or not enough for people. (Shoutout to my friend’s skeptical mom.) And that doubt makes you doubt yourself, too, until you don’t even know what it is you want anymore.
This is why I’ve learned to keep my ambition to myself. It’s no longer something I talk about with anyone and everyone.
Last weekend, I met up with a friend for brunch. It had been a couple of years, and she asked what my goals were. I found myself lying. “Oh you know, nothing big,” I said. “I guess I don’t really have any goals.” Of course, I knew damn well I did. I thought about all the stuff I wanted to do at my new job. And the dream publication I’d been pitching for months. And the new project I want to start at my community library. I couldn’t bring myself to say any of it.
It's my ambition, and I guess I want to keep it that way.
Kristin Wong is a journalist and freelance writer who has written for The New York Times, The Cut, Glamour magazine, and ELLE. She is a writer and researcher at Hidden Brain Media, where she contributes to the Hidden Brain radio show and podcast. You can find more of her writing here and follow her on social @thewildwong.
Image: d3sign/Moment via GettyImages
Do you have a story to tell about how asking for more has played out in your own life — for better or for worse? Let us know in the comments.
And remember to join us for more conversations like this one by subscribing to “Too Ambitious”.
You can also check out the conversation Kristin and I had about this piece and the ways we continue to grapple with our ambitions here