I couldn’t tell you what the meeting was about or exactly when it happened — probably a year or so into my first job at a tech startup — but I feel certain I was sitting at a meeting room table and listening to someone go through a slide deck when the thought struck me: Maybe I should get an MBA.
Somewhere, a record scratched. Who had I become? Well, I’d become an ex-writer — a frustrated journalist who hit 30 and felt like her career wasn’t matching her ambition and then pivoted into the MBA- and dude-heavy world of tech startups. Partly because I was worried about not saving for retirement, partly because the job afforded me the opportunity to move to a new city where I wanted to live. Most of all, though, I felt like I’d been stalling professionally. My future in journalism seemed less than bright, and switching industries seemed like the only way to move forward — even if I didn’t know what I was moving toward.
For a while, I went all-in. I became a copywriter, then moved into a strategic marketing role. And so maybe it’s not surprising that when I spent my days being told what to do by powerful people (for the most part, men) who had MBAs themselves, I began to think I should follow the same path.
It felt like a weird thing to consider: Never before had I aimed to start a business or to join a C-suite. (Never before, in fact, had I known what a C-suite was.) But immersed in this new world and bossed around by these new people, I began to doubt whether I’d been doing myself a disservice by not going after the same things for my own career. I might not know what I wanted, but I knew I didn’t want to settle.
“It can be helpful to disentangle two questions: ‘Can I do it?’ and ‘Do I want to?’”
This is a thing about ambition: It takes a lot of personal strength to be surrounded by people who are all reaching for the same brass ring and not think that you should be reaching for it too — regardless of whether you really like brass, or rings.
Lisa Sanchez, a San Francisco–based leadership coach, often comes across this phenomenon in her work. Her advice: At every juncture, think critically about whether the next step matches who you want to be, or whether you’re letting yourself be pulled along by someone (or something) else’s momentum. “Ambition works best when we let it drive us in the direction of our deepest values. It can be so helpful to disentangle two questions: ‘Can I do it?’ and ‘Do I want to?’” Sanchez says. “Just because you can doesn’t mean you have to.”
In the moment, though, it can be difficult to disentangle those two things. Disappointed by the outcome of my writing ambitions, I didn’t ask myself if I wanted to be a tech-world striver. I just started doing it, because that seemed like the right thing, the thing everyone else seemed to want, the thing I should want for myself. It seemed like progress.
In the interview process for my next tech job after that first company, a co-founder asked me where I saw myself in five years. “I’d like to start my own company,” I said, which was something I’d come up with on the spot and had never considered doing.
The co-founder frowned. “Why aren’t you doing that now?” he said.
Immediately, I felt embarrassed, like a slacker who had fallen short of expectations. “I have more to… learn?” I said. It seemed to work: I got the job. I hated the job. After six months, I got laid off from the job — partly because of budget cuts, and partly because, as my then-boss said, I “wasn’t a culture fit.” It was a huge relief. And a time to do some reckoning.
Specifically, time to do some reckoning about how I’d gotten to where I was — about what success looked like to me and how that could, and should, change. “Especially for those who are underrepresented, we’re often contending with messages from society, our inner critics, and individuals in our lives who tell us we can’t achieve a certain definition of success,” Sanchez says. “Our ambition compels us to prove them wrong.” I certainly felt that compulsion; until I got laid off, I was determined to try to win at work — even though I didn’t want the prize.
Unemployment was scary, but I also felt very free. Thanks to a severance payment and a well-timed freelance gig, I finally had a little space to think about what it was that I wanted from my career and my life, not what other people would expect me to want.
When her clients are trying to make decisions, Sanchez says, she typically asks them, “Will it help you become the person you want to be?” The person I wanted to be was not someone climbing a corporate ladder. I wanted to be someone who did a corporate job with competence to support the other things I wanted to do in my life. That meant having health insurance, traveling to spend time with my family, and writing things that I wanted to write without having to worry if the writing would pay the bills.
Some might say I was overqualified for my next job. But it was the perfect role for me. It required a pay cut, but it didn’t require me to give anything beyond what I was comfortable giving: my attention for 40 hours a week, with comfortable lunch breaks. I went home in the evening with a spring in my step and enough mental energy to write and publish a book. A previous boss once suggested that I take a sabbatical to have time to find a partner (an insane idea that, under the circumstances, actually felt like a reasonable suggestion). At this new job, I had time to meet someone and fall in love and get married. When people celebrated “big wins” and clapped each other on the back for “crushing it,” I just sat there and smiled. I knew that I’d never be a big fish in their sea. I’d poured out that cup of ambition. And I had never, ever felt so powerful at work.