That Time I Sucked at Being an Assistant
Summer 2019 marks my—deep breath—20th anniversary of moving to New York City which in turn marks the 20th anniversary of my first job in magazines . . .
So, to commemorate the occasion, I’m re-entering the blogosphere with a stone-cold truth about my first job as assistant-to-the-editor-in-chief of CosmoGIRL!. Full disclosure? This post took me almost two months to write and changed directions approximately 12 times. The self-editing process certainly made me appreciate all the editors I’ve resisted over the years (but more on that in another post). For now, I wanted to capture the reality of what happened AFTER I made my big move to NYC and nabbed the exact job I coveted. For an introverted-extrovert who purposely avoided major social experiences (no thank you, sleep-away camp) and cried tears of anxiety the whole 4-hour drive to college—moving to NYC jobless and basically friendless never fazed me. It was what I was supposed to do—no, it’s what I was meant to do—and it never occurred to me that I should second guess or doubt that instinct. I leapt forward without a net—bold, confident and fearless. I wish I’d bottled up that “I WILL take over the world” attitude because many times since then, I’ve had to dig deep to retrieve even a fraction of that valiant and audacious girl . . . she’s there but it takes a bit of coaxing to get her going and over her fear of screwing up. Ironic since during the first few months as an assistant (okay fine, EVERY month in the job)—I did screw up . . . A LOT . . .and it wasn’t pretty.
Yes, perhaps it was “imposter syndrome” or jangled nerves or inexperience but my strong desire to succeed didn’t make up for the fact that I was out of my element. I had no concept of syncing a calendar or tactfully interrupting a meeting (even with permission). I fielded phone calls from big wigs in media and sometimes would drop newsworthy names like, oh, you know, Monica Lewinsky, as if she was marketing spam. Due to a series of miscommunications stemming from before my tenor as assistant, my boss was three months behind on her American Express card. It was my mess to straighten out—and chaos ensued. Imagine the fun of a 5am wake-up call (on a Saturday!!!) upon a hotel reservation getting declined—during a business trip . . .
While the AmEx was my problem but not my fault, I initiated my own share of mistakes . . . like forgetting to reschedule a big meeting with the top editors that set everyone back on a huge deadline—causing them to work a weekend—creating a domino effect where they all took a turn laying into me. I did what any green, newbie assistant would do—denied my wrong doings, took zero responsibility and fled to McDonalds to eat my feelings, ugly cry and pray HR wasn’t cleaning out my desk as I polished off my Big Mac.
Another thing? I wrongfully assumed that because the youngest editor-in-chief in history hired ME as her assistant that it meant that I too was a big deal. Why else would she have chosen me out of all the other chic and experienced applicants? Alas, it was quickly apparent that I was not CosmoGIRL!’s other “it girl”—though my ‘tude often suggested otherwise. Before CosmoGIRL!, I’d been a measly intern for eight whole weeks at Rolling Stone . . . yet I had the gall to say things like, “Well, at Rolling Stone, WE did things this way . . .” WE??? I barely had building access!
I believed I tried my hardest and did my best—yet when I thought praise was imminent, I’d get scolded over something I didn’t see coming (and deserved to be scolded for, I know that now). That disconnect, however, tripped me up, tied my tongue and shook my confidence to the core. Moving to New York City and nabbing my “dream” job happened so fast, I didn’t have time to freak out. I didn’t even have time for it to swell my head. It simply never occurred to me that I wasn’t cut out for this particular job—or worse yet, wasn’t cut out for the magazine industry until I started losing sleep, wondering if my boss regretted hiring me, was embarrassed I represented her or wished she’d gone with the thinner and more experienced girls that I knew for a fact were after my job,
I worried that I’d never move up from assistant-land unless I woke up a size two, learned to correctly pronounce the names of designers (note to self: Miu Miu is not “Moo Moo”) and “polished” my overall sense of being—and style. Yet, I somehow managed to pitch AND get assigned not one but TWO features for the big summer music issue. I was sure this meant my status at the magazine was on the upswing until another assistant—one who started months AFTER me—received the very first promotion of our small, inaugural staff.
What? I was writing TWO features. Not sidebars, not quarter page copy—FULL PAGE FEATURES (yes, plural!!!)
Everyone clapped and cheered as the “Good Assistant” (that’s how I perceived her—and yes, I was “Bad Assistant”) was bestowed the title of associate editor. She soaked in a shower of congratulations while packing up and moving to a new desk in the “big league” section of the office.
What did I do? Well, at the time, I lost my damn mind. Looking back? I actually received my first real lesson in success and tough love (they go hand in hand). But in the moment, jealousy infiltrated my body. Anxiety pulsed from my head down to my toes. I couldn't concentrate or stop agonizing over what this meant. I was positive her success simply signaled—and confirmed—my doom. I was such a brat that I couldn’t even utter “congratulations” or muster a high five to “Good Assistant.” Instead, I shot death stares as she waltzed into closed-door meetings and pitched groundbreaking content. I languished in assistant-land, making car service arrangements and sorting out overdue expense reports—only entering closed-door meetings to set up a conference line or take coffee orders. I decided she was my arch-nemesis for no other reason than she was projecting everything I could not.
But, not long after, something started to click. My two features were well received. I didn’t run into the bathroom to hyperventilate every time I had 12 hours to create a slideshow that my boss needed yesterday. I could foresee and avoid problems—little things like telling the car service I needed them out front two hours before an event instead of minutes or printing out the next day’s calendar before I left for the night. By no means was I perfect (20 years later and that damn AmEx is probably still delinquent) but my expectation of things to fall into place without putting in the effort started to dwindle . . . I finally accepted that “Good Assistant” didn’t “luck” into her promotion because her boss didn’t have an overdue expense account to trip her up.
And there was another thing—while “Good Assistant’s” promotion was a wake-up call and a game changer for me—she was ready for it. I had to accept that even with opportunities like my dual bylines, I wasn’t quite ready for the heightened exposure and pressure she now had to navigate. “Good Assistant” also didn’t wear her insecurities on her sleeve like I did. Sure, maybe on the inside she felt out of her league, but “Good Assistant” projected confidence like an industry veteran. I stuck my foot in my mouth and blamed my frequent and uncontrollable tears on “allergies.” She already knew the subtle art of humility almost two decades before I even came close. “Good Assistant” got promoted by not only being a team player but also “playing the game” well. Me? I acted out like a little kid whose turn got wrongfully “skipped” . . . And, it took me a long time to understand that “Good Assistant’s” promotion didn’t mean my turn was “skipped” permanently.
Hence why the biggest lesson I learned then is that success doesn’t come in limited quantities; you don’t need to fight for it like a limited-edition handbag. There’s enough to go around for everyone as long as you don’t allow success’ evil cousin, jealousy, to stand in your way. Jealousy clouds judgement— though by recognizing it’s taking over your brain you can then take a step back and have a deep self-talk. Ask yourself what you REALLY want to achieve, how you’ll feel once you attain it and what about someone’s else’s success bothers you the most. Pinpoint exactly what you’re jealous of so you can get clear on where you’re stifled. Write down all your goals and list all the steps needed to achieve them—on your terms. That’s your roadmap for your own unique journey—a route where you won’t need to worry over who did it first, who did it already or who did it better.
Now, twenty years and a million professional experiences later and I can assure you that I’m not perfect. As Nick Jonas says, “It's my right to be hellish, I still get jealous.” But it’s only fair to admit that my turn for a promotion actually came not too long after “Good Assistant’s” when an associate level job opened in the entertainment department. I didn’t even think to apply for it and never thought it was mine for the taking—but my boss saw it differently. Yes, I was still green and not completely ready, but I’m forever grateful that she recognized that the opportunity was not only rare but also completely necessary if I were to ever have a shot at pursuing a pop culture driven career path.
Or maybe she was just sick of my inability to get her AmEx paid off . ..
Now, I have a lot more to say about getting acclimated to my surprise promotion in a coming post but here are my closing takeaways on success, competition and jealousy:
Everyone gets their “turn”—you must be patient and trust it’s coming. You may not get it when you think you’re ready OR when you least expect it . . .but whenever you’re tapped—trust that your time has come. Go for it, don’t say no or worry what anyone else thinks.
Every job and every task—no matter how menial you may believe it to be—is training for your next step up. Managing someone else’s calendar taught me how to keep up with my own. Sorting through the mess of the AmEx taught me how to project manage. Answering someone else’s phone and needing to “sweet talk” power players taught me how to butter up publicists and book celebrities . . . I could go on but treat every task as “training”—no matter how futile they might feel.
“Good Assistant” and I finally had a moment. . . okay fine, I sucked it up and congratulated her MONTHS after the fact because, you know, baby steps! But seriously, even today I still look to her as light years ahead of me—and I couldn’t be prouder of her success OR more thankful for the kick in the ass her success can STILL give me!