My Life as an Unhappy Overachiever

I had quit nine jobs, I wasn’t even thirty, and I cried in the bathroom almost every day.

I was about to give a speech at my alma mater and was nervous (as was the Brown Alumni Relations staff!) because I planned to get raw. In front of a room of two hundred successful women, I was going to share the story of how I became happy at work only after I realized that the idea of who I wanted to be was making me anxious, destructive, and depressed.

I was nervous but also elated as I approached the podium. As I began to command the large hall I’d walked by many times as an anxious, and often sad, undergraduate, I felt free. “If you knew me at Brown, I don’t think you’d have expected I’d be keynoting this dinner,” I opened.

“I have the dubious distinction, of being an ambitious risk taker who also struggles with anxiety and depression. This has forced me to learn some very helpful coping mechanisms, and I want to share some today with you.”

But first, I told them, there were the panic attacks. That time sophomore year I couldn’t get out of bed for a week. Hiding in my dorm room, and then, when I graduated, in my apartments. How I sought geographical cures, moving to different cities, like London, and even farther-away continents, like Africa. How I did a fair amount of drugs—the worst of which, ironically, were by prescription.

I talked about how, as a young woman, I wanted so badly to be liked, and to do everything right. I felt it was expected of me. I had been the kid who cried at sleepaway camp and wouldn’t let my mother and sister leave my first night at college. I only wanted home, and comfort. Instead I dealt with its absence like many young people do: through eating, drinking, and hookups.

I told them how, because I was very ambitious and driven, I went for every big job and opportunity I could. How I kept getting promoted, and I kept being miserable. The work was easy, but the office politics, the hours, the pace, networking, and rules of getting ahead rubbed up against my very temperament. I was living out someone else’s climb up the ladder, and I was fighting a losing battle.

I had quit nine jobs, I wasn’t even thirty, and I cried in the bathroom almost every day.

I talked about the day I realized that who I was and what I was doing every day were completely mismatched.

It was during my final corporate job, when, under the ubiquitous fluorescent lights, I realized I was allergic to them. They give me migraines. And as long as I had to show up and sit under those lights for ten-plus hours a day simply because I was expected to, I could never be happy.

I know now that I was caught in a cycle of achievement, of working hard for someone else’s dreams or expectations, and not my own. It was only when I accepted that I needed a quieter life, needed to reframe success on my own terms, and figure out the tool kit I needed to get there, that I could find joy at work. Becoming “less successful” set me free.

Not exactly your typical go-get-’em women’s leadership speech. I looked around the room and was terrified. Would the under-grads and alumnae think I was a nutjob? I had worked so hard on the speech, and it was the first real keynote I had delivered.

The speech got a standing ovation, and I felt like Oprah.

Growing up, I was sent to the best private schools, and it never occurred to me to do anything less than achieve. Those of us fortunate enough to be raised with expectations of academic or financial success learn that when we achieve, we garner praise and positive attention—even if we’re faking our own enjoyment. Through childhood, adolescence, and into adulthood, we keep achieving, craving the external validation that comes when we get all As or are chosen to captain the team. I was, and am, extremely ambitious. But the more we achieve in order to win the approval of others, the further we get from our own goals—and happiness.

A recent Duke study found that women who graduated in the 1970s were much happier than those graduating now, and had far more self-confidence. The report concluded that the women who graduated in the seventies cared less about what people thought about them, and were able to take risks—such as pursuing a nontraditional career or starting their own business. In fact, women seem to be increasingly less happy, even as they achieve more professionally.

Ambitious and privileged young people on the path to college are raised with a narrative of achievement—a surround-sound, multi- faceted version—that no generation has experienced before. Do the most extracurriculars. Have the perfect internship. Get a great first job. Build your personal brand. Run that marathon. Eat organic. Get perfectly hairless and smooth. Fuck perfectly. Navigate dating. Enter your thirties, find a partner, conceive, and give birth (naturally, of course). With the addition of social media, you’re supposed to share it all, too—as you suffer the FOMO of watching everyone else seemingly sail through life.

I’ve found that it is especially hard to achieve in a traditional career ladder scenario if you are an introvert, and if you need more control over your space, pace, and place of work than others. Let me be clear: this has nothing to do with laziness, or lack of ambition. Your need for a different kind of workday has nothing to do with the level of effort you will put in, or the drive you possess. That’s in-grained in who you are just as much as your need for quiet or alone time. When you work differently, it may even mean you work harder than someone who’s spending plenty of time at the office surfing Gilt.com. I may be a hermit who rarely eats lunch with anyone, but ask anyone who knows me and they will agree: I work hard and I am driven as hell. (They don’t know I’m usually working in bed.)