9 years ago I had a degree in English and a job selling ballet shoes for barely above minimum wage. I had left Vassar the year before assuming that a job would make its way to me in the way jobs did in the books I grew up reading, in which smart people made livings that were rarely germane to the plot itself. Vassar had a Career Development Office but my vague sense was that it was for people with callings, and I knew I didn’t want to be a doctor (blood!) or a lawyer (paperwork!).
Nor did I bother with unpaid internships in publishing or media; I wanted to be a writer, maybe, but not enough to fetch coffee, and the inequity of being able to afford that made me feel a little grimy. I felt guilty enough that I didn’t owe student loans, and anyway, I liked the dignity of selling shoes. I had liked spending my summers back home at the dancewear store in Las Vegas that hired me when I was sixteen — a dream job for a ballerina who needed gas money — earning an honest living getting my fingers trampled by toddlers in tap shoes.
It was easy to move back home after graduation and get my head on straight before I went back out to seek my fortune. I thought, too, that the people handing out the jobs would be impressed by how my store had given me a set of keys to the place and trusted me to ferry cash to the bank. Surely that was more qualifying than coffee-fetching (someday someone will need to tell me what one actually does at a magazine internship if it’s not coffee-fetching).
Not so much. In 2011, I’d have been better off reading the news than novels set in eras not characterized by global financial collapse. I moved to New York with the money I’d saved and transferred to the dancewear store’s location on the Upper West Side, where the cocktail waitresses who paid for fishnets in stacks of ones gave way to old women with enormous dogs that they brought into the store to wait while they tried on slippers for their adult beginner jazz classes at Steps. I was just one of the army of humanities majors emailing resumes into the void, most better suited than mine for working under a fluorescent light.
I applied for every job under the sun and one after another, they rejected me. Nobody seemed to believe that their job was what I really wanted to do; I remember the woman interviewing me to write copy for an online catalogue of machine parts who asked me if I really thought this was going to be interesting (no, but who would? And Kafka worked at the post office!).
The heavens opened when my sister’s husband mentioned that his company might hire me to write proposals. I knew that at his previous company he’d gotten to fly on some executive’s private jet, so this new one seemed like kind of a step down, but it was Silicon Valley. (That was still a good thing in 2012.)
I was surprised to be hired, and maybe more surprised that I liked it so much that it took me 9 years to leave. 9 years! What happens in 9 years? Six apartments, three boyfriends, one husband. Three presidents. A heartbreak, an eating disorder, an IPO, a pandemic. I learned how to write proposals and run a social media account; I learned strategy and spin. I made some money. I got airline status.
In the photo on my employee badge you can see the faint traces of a sunburn from the hike my dad and I took up Mount Charleston a few weeks before. It had been as humid as it gets in Palo Alto on my first day, and I’d ridden some wretched Peninsula bus to the office. My bangs had puffed up like an American Girl doll and the sleek braid at the back had frayed wildly. Every day for 8 years — until 2020, when no badge was required for me to commute from the side of the kitchen table where I ate breakfast to the side of the kitchen table where I conducted business — I stared at that godforsaken photo and marveled that anybody had thought it prudent to take me seriously.
After months of being rejected as an answerer of phones or an enterer of data, I could hardly imagine that I’d been hired for anything other than my connection to my brother-in-law, never mind the gauntlet I’d been put through. (This was the golden age of Silicon Valley “gotcha” interviews and while nobody asked me how many baseballs fit in a 747, I was told to write, longhand and without reference materials, an essay about one of the company’s products. After, I was sent to lunch with the interviewer, who brought along his hardcover copy of Ulysses. We later became good friends, but that was one indelible first impression.)
I’ve always felt like a bit of a dilettante. I picked up ballet late and was only kind of good at it. I was usually the second string — the understudy — and I often felt that I had been cast because a choreographer who needed a body liked my tenacity or my wit and could choreograph around my inability to do, I don’t know, cartwheels on the left, to name an example from 17 years ago that I remember like it was last week. I was used to accommodations being made for me, and I didn’t see why the job I’d coattailed my way into was any different.
I never quite shook that. Even as my multibillion-dollar, now-public company was handing me things like the Twitter password and managerial responsibility, I was still looking over my shoulder, sure I was one misstep away from being fired. (Deep down I’m still my 22-year-old self; it’s no wonder I still carry my 22-year-old’s insecurities.)
I think it’s still en vogue to call that “impostor syndrome,” but it was reasonable for me to work like I needed to prove myself. I know now that any hire is a bet, especially a kid with raw talent and a strong personality, and it could easily have gone the other way. And I don’t want to be a vest-wearing Silicon Valley wunderbro whose undying faith in himself is religious in fervor.
Two weeks ago I got to perform the rite I’ve long dreamed of: sending my goodbye email. (I don’t know whether this is as storied a tradition elsewhere as it was at my former employer, but I started noodling over subject lines years before I started interviewing for new jobs. I spent a full hour hand-picking recipients for the bcc line.)
It was a real Sally Field moment for me when the responses started rolling in: My first boss called me “an institution.” Not one but two of my teammates did full-body recoils when I told them I was out — though more likely because they knew exactly who was picking up the slack upon my departure. Our COO, whom I have harangued for years with emails about everything I think he should make our company do differently, told me he was grateful for me.
It didn’t jibe with this picture I still have of myself as the sunburned 22-year-old with the Molly-doll bangs, ostentatiously copyediting everything I could get my hands on to prove I had some unique value. I think I thought everyone was tolerating me until they could install someone who actually knew what they were doing in, as if they were my college choreographers settling for a second-tier body and not capitalists with the no-fault ability to fish for something better in a teeming labor pool. I had braced for the nostalgia but not the late-breaking discovery that 9 years ago, I tripped into my calling.
For a moment I backpedaled. These people like me (they really like me!); what am I doing? But I felt like I did at the end of senior year at Vassar: like I was going out on top, and from there, I could see back down to the bottom. My star had begun to fade. My company was the kind of place where you had to constantly reinvent yourself to stay relevant and I did, I lived 9 lives in the 9 years I was there (you should have heard me trying to explain my resume to recruiters when I was locking down my next act), but you can only carve so many matryoshka. I wanted a fresh start in which my baseline was not me, age 22, ruinously insecure yet blithely confident in my own capabilities, a muckety-muck’s kid sister-in-law.
My new baseline has crows’ feet and gravitas. I turned down offers to accept this one and I hardly remember anymore what it was like to sit under the fluorescent lights of an office in Westchester and admit that I couldn’t use Excel. I can nod knowingly back to everything I did these past 9 years, the proposals, the IPO, putting lipstick on this and that boondoggle by calling it a “strategy” and dressing up the failures I performatively take the blame for. I can sort of use Excel.
I’m as nervous to dive into my next job — at a company a tenth the size of my previous one where I’ll be the only person doing what I’m doing — as I was nine years ago. The only difference is that now I know I can fake it ’til I make it, or, more precisely, that I can fake it, indefinitely, just like everyone around me is doing, because all of us were once 22-year-olds who forgot their sunscreen and grew up in a world that wasn’t the one we were promised in books.