The Smart Money Would Not Have Been on Me

Or, how naïve ignorance got me where I am today.

A NOTE TO MY REGULAR READERS: This post is not me shining a scathing light on some new, nefarious corruption scheme. It’s not a delightfully snarky takedown of a deceitful dictator or even a lighthearted look at my own mortality (yes, there is such a thing). Today’s post features an essay I wrote for an anthology (someone else’s!) that never happened. It’s the story of how I became a writer and has nothing to do with the insane-clown-posse-world we live in today. Or in a way, maybe it does. Regardless, I came across it and it got me all nostalgic, so I’m sharing. If it isn’t your cuppa tea, feel free to move on. I will resume regular Covidy commentary this week.

All the White Wrong Moves

The lobby of the towering waterfront high-rise was teeming with police when I showed up for work. It was the day before my 23rd birthday, not that it mattered.

“Weird,” I muttered to myself, making my way to the elevator bank. The sixteenth floor was another sea of badges and blue. This was Florida in 1992; nine-eleven hadn’t happened yet and active shooter situations weren’t making headlines every other day, so my mind didn’t at once go to terrorist attacks or mass executions. The ad agency where I worked as a copywriter was in a bank building (and the bank was a client), so it was probably just another holdup.

I made my way to the company kitchen for some burnt coffee-flavored water.

“What’s going on?” I asked the small group gathered there.

“We lost Winn-Dixie,” one of the graphic designers explained. Winn-Dixie was our biggest, most important client. “They’re laying off half the staff.”

“Poor bastards,” I thought but thankfully did not say aloud. (In my defense—which will absolutely be the name of a future book—I’d been hired away from a better paying sales job and my salary was barely above peanuts. Why would they lay me off? I practically worked for free.)

When my boss Zoe Ann called me into her office to tearfully inform me that I was in fact one of the aforementioned poor bastards, I was actually stunned. She gave me a box to collect my things. I didn’t have any things.

“So do I just, like, leave?” I asked her. She nodded and told me HR would be in touch.

I took the box to my office, stole a stapler and some sticky notes, and drove home in a daze. It was ten o’clock in the morning on a Thursday. I had nowhere to go and nothing to do.

I waited until the day after my birthday to call my parents with the delightful news. Since I was about to have no way to pay my rent or make my car payment, I figured they should know I may soon be living back at home.

“What do I do noooooow?” I sobbed into the phone.

“You file for unemployment,” my dad roared back. “It’s your money! They took it out of your check every goddamned week. You’re entitled to it.” (It turns out Dad was wrong about where that money came from, but might is right and Dad was always the loudest and therefore, unimpeachable.)

In 1992, “filing for unemployment” didn’t mean logging into a website, clicking a few boxes, and collecting a check. Oh, no. It meant driving to the sketchiest part of town, standing in an endless line with the literal unwashed masses, being interrogated by a clichéd, mirthless robot (they’re clichéd for a reason) who would demand documented proof of your relentless job search and your registration with every employment agency in town. Every single week.

After my second visit, I realized that collecting unemployment was a full-time job that frankly didn’t pay all that well, so I started job-hunting in earnest. I didn’t have to look for long. As is often the case, the worst thing that had ever happened to me turned out to be one of the best.

“We’re running with a skeleton crew over here,” Zoe Ann explained on the phone. “Are you interested in doing some freelance writing?” When she told me the agency was willing to pay me five hundred dollars for a bank brochure I could write in a few hours, I may have lost consciousness for a second or two. Did they even realize that my salary as a copywriter at the very same agency had been sixteen thousand dollars? A year? That meant my take home pay had been in the not-very-affluent neighborhood of two hundred bucks for an entire week’s work.

I could crank out four brochures a day, seven days a week! I was going to be rich!

Even as my portfolio grew, minimum balances and monthly service fees were hardly titillating topics. I yearned to write about exciting things like relationships and pop culture and psychology and sex. Leaning on what I had learned in a freelance writing class I’d taken in college, I began submitting my finished, unsolicited work to the top national women’s magazines. You don’t do this, of course—you pitch carefully fleshed-out ideas and only after you’ve studied each publication’s editorial calendar and know every topic they’ve covered since the beginning of time—but they forgot to teach us that at Florida State University.

I don’t even remember the subject of the uninvited article I sent to Vogue (yes, that Vogue), but I can recite verbatim the call I got from the editor I’d sent it to.

“I love your writing style,” she told me. “But I can’t use your submission.”

“Oh, well, it was nice of you to call,” I stammered.

She wasn’t finished.

“I’ve actually given my two weeks’ notice at Vogue. I’m going to be the Fashion and Beauty Features Editor at Seventeen and I’ll be hiring a writer. I can’t pay to fly you to New York” —as if!—“but if you can get yourself up here, I’d love to interview you.” 

My teenage Florida bedroom walls had been plastered floor to ceiling with pages ripped from Seventeen magazine. Seventeen magazine had taught me What Makes Me Go for the Wrong Boys (quiz on p. 72) and why I should never pop my own pimples or curl my eyelashes after I’d already applied mascara, even though I occasionally still do both. I’d found the prom dress of my dreams—a lace covered strapless Gunne Sax number in the perfect shade of dusty rose—in Seventeen magazine. And now I was going to be standing in the actual, physical space where that very magic was routinely made. I’d never get the job and I was okay with that. The fact that I even qualified for an interview was a fantasy more farfetched than any this girl who’d grown up in Daytona Beach, Florida, had ever dared to entertain.

The actual dress, which was All That circa 1985.

My parents offered to pay for my plane ticket, so I went to Stein Mart and blew the last of my meager savings on a clearance rack Donna Karan suit and matching lace top. The pleated palazzo pants were a smidge too big, but you couldn’t really tell if I kept the shoulder-padded jacket buttoned.

Did I mention that this designer disaster was solid white? And that Seventeen was in New York? As in, the city? Just making sure.

LEFT: My wonderful aunt met me in the city and snapped this photo the day of the interview (the jacket was still hanging up because I didn’t want to wrinkle it, and you are correct that I am pretending to peruse my “portfolio” of bank brochures I’m not cringing, you’re cringing). RIGHT: My youngest daughter—who now lives in NYC—wearing the very top (not one like it) and recreating this photo three decades later, and yes I save everything.

The editor’s name was Jennifer, and she was the most gorgeous, glamorous creature I’d ever seen in real life. She had a Kate Moss body and wore a skintight black—of course black—floor-length, sleeveless knit dress and my mind couldn’t wrap itself around the fact that Jennifer and I were both the same breed of animal or that people actually went to work looking and dressing like that. I’d read about “glowy skin” plenty of times but Jennifer’s skin actually glowed. Women in Florida didn’t look or dress or glow like Jennifer did. When she offered me the job, right there during my interview with my dull complexion and sporting that milky mishap, I said yes. Without asking what the salary was or worrying about where I would live or how I would get myself and my things and my four cats don’t judge to New York in fourteen days or how the dark and smelly subway system worked anyway.

Yes, Jennifer, I’ll take the job. A thousand times yes.

Two weeks later, I was living in New York City and working at Seventeen. To say I was out of my league would be like saying porcupines don’t make the best cuddle buddies. Seventeen was staffed by real-life debutantes and daughters of renowned New York Times journalists. Most of them wore designer everything and had flawless highlights and advanced Ivy League degrees. I was the white clearance rack suit-wearing child of a high school dropout with box-dyed hair and a BA from the University of North Florida. (I’d transferred from Florida State senior year, even though I’d continue to say vaguely I’d ‘gone to FSU’ because obviously it was the much more prestigious university.) These women—hell, most of us were nearly still girls—shopped at Bendels and got regular blowouts and had shares in the Hamptons. At the time, the majority of my “wardrobe” came from The Limited, I’d never had a salon manicure in my life, and I could barely afford my first rent. Even though Seventeen paid me more than twice what I’d made at the ad agency, New York was expensive. Forking over for a second summer place to use on weekends was an unimaginable luxury that did not fit into my budget.

The advertising agency had been an old boy’s club, a setup I figured was pretty standard. My direct supervisor had been a woman, but the entire c-suite was made up of men. They occupied a separate floor above us “creatives,” where they sat in high-back leather wing chairs behind massive mahogany desks. (We sat on squeaky rolling chairs at laminate workstations, although we both shared breathtaking views of the St. Johns River.) The seventeenth floor reeked of cigar and cigarette smoke—people puffed in their offices back then—and power and money.

Conversely, other than two male editors and the art director, the editorial staff at Seventeen was comprised entirely of women. The masthead read like a sorority roster, with Midge, Nancy, and Catherine claiming the tippy-top slots. My boss’s boss’s boss was a woman. It was dizzying.

The masthead from the very first issue of Seventeen that featured my name, which my sister—the most thoughtful human on the planet—framed for me.

I’d minored in French in college and done a semester-long language immersion program at the Sorbonne. “Language immersion” means they do not, for example, tell you that “Ouvrez vos livres et fermez vos bouches means ‘open your books and shut your mouths’;” they simply shout it at you every morning when you get to class and you’re left to figure it out.

Women’s magazines were a lot like that.

“Whose skirt is that?” I heard one gazelle ask another in the elevator one day. Relative to say, women in general, my colleagues weren’t slender; they were skeletal.  

“Ralph’s,” the second replied.

Wait. What? She’s wearing some guy Ralph’s skirt? (Today that might not seem such an oddity, but in the 1990s, gender was a lot less confusing.)

“Really? I totally thought it was Guess.”

Ooooooh.

Right.

Of course.

They meant the designer.

(It’s pronounced LAURen, incidentally, not LaurEN, despite what your provincial Florida friends think.)

Mental note: Do not reply “mine, why?” when someone asks you whose skirt you’re wearing.

For the record, nobody ever asked me whose skirt I was wearing. Not even once.

Not entirely inaccurate.

It could have been a disaster. It should have been a disaster. And if I’d known in advance that I was going to be Kristy McNichol trying to fit in with an army of Tatum O’Neals, I might still be in Florida writing bank brochures. But ignorance is bliss, and I was downright ecstatic.

I loved my job. I loved working with smart, creative women. I loved everything about fashion and beauty and spending my days up to my elbows in both. I loved replying, “I’m a writer” when people asked me what I did for a living. I loved imagining my old classmates back home saying, “Did you hear Jenna moved to New York City? She works at Seventeen magazine!” I loved calling it The City, as if there were but one and I got to inhabit it.

[Side note: When I moved to LA years later and people would ask me if I was in The Industry—as if there were but one—it bugged the shit out of me. Go figure.]

I’ll be honest, the perks of working in publishing didn’t suck. Cosmetics companies from MAC to La Mer would courier their entire collections to me to sample (and yes, keep) several times a year. Celebrity stylists like Oribe and Oscar Blandi would cut, color, and style my hair for free whenever I wanted. I had middle-row seats to all of the NYFW shows. For once, my size-ten feet—the embarrassing bane of my teen years when the two most popular pastimes, bowling and roller skating, involved footwear that displayed your size right on the back—actually came in handy, as ten just happened to be the sample size designer shoe companies sent over for shoots (and incredibly, didn’t even want back). While I had little else in common with the waifish, willowy models Seventeen routinely featured, it turned out most of them, like me, had paws the size of snow shovels.

Holidays in those hallowed halls were an embarrassment of riches, with cashmere bathrobes and Baccarat photo frames and Tiffany paperweights piling up in my office for weeks. Never mind that it was my job to write about the generous senders’ potions and pumps and ponytail holders. I guess it never hurt to get on a writer’s good side.

When Jennifer informed me she was moving magazines again, I was terrified they’d replace her with one of the sadistic she-devils our industry was famous for circulating. My fears were not baseless.

Her name was Sally (an outright lie because more than thirty years later I’m still terrified of her). Unlike most of my other coworkers, Sally wasn’t stylish or attractive. Nor was she a very good writer or editor. Rumor had it she’d been fired from a long string of magazines and I could not, in fact, figure out why anyone would hire her at all. I don’t feel bad saying any of this because never in my life had I met a woman as arrogant, insolent, or downright unpleasant as Sally. I still haven’t.

On her second day as my boss, Sally marched into my office holding a pile of papers.

“Where are we supposed to put these?” she demanded.

My desk was a good ten feet from the doorway, and I could only see the back of the stack.

“What are they?” I asked.

“Never mind. I’ll ask someone who knows what the fuck they’re doing.”

In a blur of mousy brown hair, she was gone.

I cried a lot when Sally was my boss. Thankfully, she didn’t last long at Seventeen.

This time, the publishing gods sent me a pintsized powerhouse named Liz. Only a few years older than me, Liz was a master wordsmith and a warm and inspiring mentor. She loved alliteration, a perfectly-placed pun, and razor-sharp wordplay, and we would sit in her office long after everyone else had gone home trying to outdo each other with our linguistic brilliance. Liz was funny and wise and everything that was good about women’s magazines and to this day I can’t write about a festive frock or a particularly pointy pencil without thinking of her. Tragically, Liz lost her battle with colon cancer in 2018, an unimaginable loss and a heart-wrenching reminder of life’s fickleness and fragility.

Oh, man. Liz would have loved that sentence.

Maybe it was because I worked hard at my craft and genuinely cared about the content I was creating. Maybe it was because I was funny, or because I wasn’t the worst writer in the world, or because I really didn’t give a shit if my colleagues thought they were better than me. As far as I could tell, my inarguable fish-out-of-waterness was never an issue at Seventeen, or at Mademoiselle when I was hired there, or at Shape after that, or at any of the dozens of publications I wrote for over the next few decades. It didn’t come up when I wrote my first book or my fifteenth; never once did a publisher ask what my dad did for a living or where I’d gone to college, or even if I’d gone at all. It posed no problem when I was invited to give my first TED talk in California or my second in Budapest. Or maybe it was an issue—maybe there were clusters of upper-crusters turning up their surgically perfect noses behind my back every single time—and I was just too clueless to notice. I actually wouldn’t mind if that were true.

Always be yourself. Unless you can be a meerkat. Then definitely be a meerkat.

I’ve spoken about writing and my career path at countless high schools and colleges and do publishing consulting on the side. Amazingly, aspiring scribes often want to know how to break into magazines. Even now, still, today.

Call me old-fashioned (or just plain old), but I get it. There’s something undeniably special about print; it has a gravity and a permanence the internet doesn’t and never will. If you make a mistake and it gets through several layers of copyediting anyway before going to print, it lives in the world that way forever. Pressing open a publication’s pages and gently tearing out your piece—they’re actually called tears when it rhymes with bears—to save for posterity feels profound in a way hitting the print button simply doesn’t.

Publishing is nothing at all like it used to be. Today anyone can publish a book or a substack. Anyone can say, “I’m a writer.” Magazines I once wrote for like Self and Glamour and Marie Claire have gone fully digital. Sometimes I feel nostalgic about it all, but mostly I’m grateful for the lessons the erstwhile industry taught me: namely, that ignorance can be your best friend, that often there’s no one precise path that leads to where you want to go, and that you’ll do yourself your life’s greatest favor if you can embrace the idea that what anyone else thinks about you is really none of your business. 

The anthology that is very much happening and soon (I’m talking books will be in the house in six weeks squeeeeeeeeeeee)!