I officially changed my Instagram handle from @adventurer to @helenaholloway the summer after my freshman year.
There were two reasons I did this. First of all, my brand had evolved beyond going to bougie locations and taking my readers along for the ride. Now, I talked more about my so-called inner world — navigating a grown-up relationship for the first time, supporting a partner who was just as ambitious as I was, dealing with envy and impostor syndrome as I tried to become a writer. It was all fake, of course, but even so, I was no longer just an adventurer. I was Helena Holloway.
Second of all, I was starting to think beyond Instagram. Writing stories for social media was working out even better than I’d hoped. By June, my account was nearing 750k followers. I couldn’t even imagine seven hundred and fifty thousand people in a room! Yet I couldn’t shake that childhood dream of becoming a published author. The more famous I got online, the more achievable this dream became. I’d idly thought about leveraging my Instagram fame into something more tangible. Why shouldn’t I go for it? Captions were temporary and small. Books were forever.
Thank goodness I’d had the sense to create a dummy account called @helenaholloway on Instagram. I wasn’t so fortunate with Twitter — I joined a little too late and ended up having to settle for @helenaholoway, with just one L. I hate misspelling my own name in the handle, and the worst part is that the original @helenaholloway account is inactive! I’m still waiting for a reply back from Twitter about this. Their customer service is truly abysmal.
Once I officially became @helenaholloway, I focused on finding the right literary agent. I needed someone who understood my whole vision, who wouldn’t force me to undergo any creative compromise. I didn’t want to make any book besides the one that was in my head. I wanted my readers to watch me fall in love, break hearts, get married. I wanted them to grow old with me, or at least the idealized version I presented them. I wanted to create the story of a lifetime, to redefine how humans engaged with autobiography. To win the Nobel Prize, even. And if an agent didn’t want precisely that, well, I didn’t want to work with them.
This meant getting rejection letters at first: loads and loads of rejection letters.
Dear Helena — Thanks for reaching out, but I don’t think that this is the project for me, since I’m not exactly sure what form it would take. I also suggest trying to place some writing with publications before embarking on a book. Best of luck in placing this with a more enthusiastic agent.
Dear Writer — no thanks.
Dear Helena — While this looks interesting, I’m not sure it’s the right fit with us. We wish you luck in your journey.
Hello — We are not certain we could be effective in placing your work. We invite you to submit more in the future.
Helena — This did not pique our interest. Do you have anything else we can consider? Please send.
It was degrading, to say the least. I mean, how could one not be interested in my story? I had almost eight hundred thousand people who would disagree, thank you very much.
Fortunately, I didn’t really want any of these people to be my agent. I’d been sending out queries as practice for pitching the agent I actually wanted to work with: Wren Falcon of Falcon Ibis Literary Agency. Young and brash, with a keen understanding of social media’s power in modern culture, Wren had worked with a number of high-profile Internet clients, from beauty vloggers to political commentators to social activists. Most recently, he’d published female pickup artist-slash-blogger Marnie Tucker’s first book, I Hope They Do Fireball Shots in Hell. Chronicling Marnie’s hilarious, debaucherous romp through nightclubs, exotic locales, seedy motels, and backseats of fancy cars, the 403-page volume had become an instant cult classic across demographics. Feminists loved her for flipping the narrative and sticking it to the patriarchy. Teenage boys loved her for her sexual forthrightness. I loved her for her business plan: give away entertaining stories about your life for free on the Internet, and then leverage that audience to get a book deal.
My only hang-up about Wren was that he published personalities, not writers. If I went with him, would my voice still be taken seriously as part of the literary canon? I wanted to be cool and smart, trendy and legitimate. And I only had one shot to get it right.
In the end, I convinced myself that society was the problem, not me. I’d already disrupted the way people used Instagram; next, I would write a book that changed the way people thought about social media and fine art. Internet personalities had as much capacity for sublime human expression as people who wrote books or dissertations or light verse for The New Yorker. And I would single-handedly get the world to see that. Once I was done, people would view influencers as intellectuals and artists in their own right.
As much as I loved my life on the West Coast, I simply couldn’t stand how chilly San Francisco got from June to August. Mark Twain had been spot-on when he’d said that the coldest winter he’d ever spent was a summer in San Francisco. The temperature rarely rose above sixty-five degrees Fahrenheit!
I wanted dresses and beach trips and long, meandering walks after dusk, not grey skies and fog and Northern Californians who thought that black puffer jackets and Herschel backpacks were the height of fashion. So it was from my old bedroom in Falls Grove that I did the bulk of my research on Wren.
It was weird being home for the summer. My mom had been promoted to partner at her firm and had to work much longer hours. My dad had gone back to work; he was now the executive assistant to a lawyer named Marcus. Instead of lively conversations and freshly-cooked meals, I woke up to sunlight and silence. I enjoyed the privacy, but it was a little jarring to discover that I was no longer my parents’ number-one priority. I would’ve taken advantage of having the house to myself, except I also had no friends in Pennsylvania. So I turned my focus to getting a meeting with Wren.
Securing such a meeting was much harder than I thought it would be. Wren’s contact info was nowhere to be found on Falcon Ibis’s website. When I finally discovered a number for his office in the dregs of Google, his secretary politely gave me an email address and told me that I could send my query to Wren there. I agonized over my wording and spent the last weeks of June waiting for a response that never came.
I was due back at Stanford in a few weeks. Desperate times called for desperate measures. I called up the Falcon Ibis Literary Agency a second time — and this time, I lied.
“Hi, Jessica,” I said in my best grown-up phone voice, remembering the secretary’s name. “This is Christina Duffy, Helena Holloway’s agent. I’m going to have to move my meeting with Wren on the twenty-third from 11 AM to 2 PM.”
“You said Helena Holloway? I’m sorry, I can’t find your original meeting on Wren’s schedule.” The poor thing sounded so confused. If only she’d known that it wasn’t her fault.
“I don’t have time for this,” I said calmly, channeling my inner Anna Wintour. “2 PM on the twenty-third is the only time my client can make it. She’ll see you then.”
I hung up before she could reply. My heart was thumping so fiercely that I could physically see the bodice of my daffodil-colored sundress moving up and down. I wiped my sweaty palms on the circle skirt, pulled my Macbook onto my lap, and created a new Gmail account.
This is Christina Duffy again, writing to confirm an appointment between Helena Holloway and Wren Falcon at 2 PM EST on July 23. Can you confirm that the address is <redacted>?
Additionally, please let me know as soon as possible if conflicts pop up. My client will be flying in from the West Coast for this meeting.
Two hours later:
Apologies for the earlier mix-up on the phone! I have Helena Holloway down for a meeting with Wren at 2 PM EST on July 23. The address you sent is correct. Please have your client meet Wren at his office on the thirty-seventh floor.
I’d always suspected that I was a good bullshitter — after all, I’d been fabricating my entire online existence — but it wasn’t until I had this email sitting in an inbox I’d created a mere hour ago that I knew it for sure.
My plan had actually … worked! I almost couldn’t believe it myself. Thanks to the power of my words alone, I now had an in with one of the hottest literary agents in the world.
The Falcon Ibis Literary Agency was in midtown Manhattan, and New York City was a mere two-hour train ride away. My mom worked in the Financial District and probably could’ve helped me out, but I didn’t want to explain what I was doing to anyone. The situation was too precarious. I had the distinct feeling that I’d jinx the whole thing if I talked about it too much. Instead, I charged the ticket and hotel room to my parents’ credit card, telling them that I was going to see a friend for the weekend. They didn’t press me for details, and I didn’t offer any.
The office building itself was a huge rectangular prism the color of a vintage Coke glass, holding forty-five stories of offices and God knows how many business secrets. I paused by the side entrance to trade my dirty white sneakers for a pair of nude pumps — a trick I’d learned from my high-powered mother — and tried not to look too much like a wide-eyed bumpkin to the people passing by. San Francisco was gorgeous, but the Big Apple it was not. Everything here was a whole new level.
It’s okay, I told myself. If you play this right, you’ll be coming back here again and again.
My heels click-clacked on the lobby’s marble floor as I made a beeline for the elevator, an ultra-modern contraption that skipped numbers by fives until it got close to the requested floor. It was almost 1:50 PM, and my meeting was at two. I wanted to be at least five minutes early, to signal that I was prompt and responsible. First impressions couldn’t be undone.
I inhaled sharply as the doors opened onto a floor that was all blonde wood and glass. The first thing I saw was a huge metal W and a huge metal L, nearly reaching from floor to ceiling, mounted to the wall. Scattered around the letters were prints of books by authors represented by the agency. The overall effect was chaotic but coherent — just like my Instagram feed! I smiled to myself, certain that I’d made the right choice.
“Hello,” I chirped to the receptionist, a guy in a yellow cardigan and red lipstick who couldn’t have been more than a few years older than me. My voice was steady and sincere. “I’m Helena Holloway. I have a two o’clock with Wren.”
“Welcome!” He gave me a warm smile as he typed a few things into his Macbook. “Wren’s office is down the hall, to the right. You’re a little early, but he should be ready to see you now.”
“Great!” Permission granted, I flounced past the reception desk into a hallway that looked like a study in the human workplace. The wall opposite each sliding door was a huge window with an unobstructed view of the city. The other three walls were made of thick glass. Colorful curtains hung at the corners, waiting to be drawn, but it seemed like no one really gave a fuck about privacy. As I walked down the corridor, I caught glimpses of people typing away at their computers, furiously editing manuscripts, laughing with colleagues about something in the corner. I didn’t know how anyone could concentrate in such an environment, but I appreciated the aesthetic. I got the vibe that Falcon Ibis was a place where people could have fun while doing serious work.
On the right-hand side at the end of the hallway was a corner office twice the size of all the others I’d seen. Forest-green curtains lined the perimeter of the glass. The overall effect was that of a small stage. Wren Falcon, read the plaque by the door.
I checked my phone — 1:59 PM — and gently rapped on the glass.
Five seconds passed, then ten. I knocked again, louder this time.
Come on …
Still nothing. I frowned. It was now two o’clock sharp. Was it impolite to knock three times?
A few more seconds crawled by. I decided to go back to the reception area and ask what was going on. I’d just taken a few steps when I heard the door behind me sliding open.
“Hello?” said a reedy male voice.
The full skirt of my dress swished around as I came face-to-face with a man whose face looked just like it did in his Twitter profile picture, down to the neatly trimmed beard, pointed nose, and intense brown eyes. It was uncanny, like seeing a painting come to life. What I hadn’t expected, however, was that he’d be shorter than me. Standing at his full height, Wren Falcon couldn’t have been a hair over five foot two.
“Can I help you?” he asked.
“I’m Helena Holloway,” I said. “I’m here for our two o’clock appointment.”
Wren looked at me like I had rabbit ears sprouting from the top of my head. “I don’t know anybody named Helena.”
The hallway seemed to freeze. Think, Helena, think. This was the moment of truth. Everything I’d done, everything I’d prepared for, dreamed about, agonized over came down to this. I wouldn’t get a second chance. How could I handle the situation so that I came out on top?
Icily, almost innocently, I looked straight into this man’s eyes. “Are you this unprepared for all of your meetings, Wren?” A beat. “Or just mine?”
Looking back on it now, I have no idea what prompted me to say that. This particular alpha move still amazes me to this day. Maybe an angel had been watching over me, or maybe the shooting star I’d made that long-ago wish upon was finally coming through.
The intense look in Wren’s eyes receded, replaced by surprise. “I apologize,” he said quickly. “I got a new assistant last month; she must’ve forgotten to copy the meeting over to my calendar. Please, come on in.”
Wren’s office was casual, almost childlike, with its bright colors and warm lighting. There was a bright blue rug on the floor. Two large beanbag chairs, one orange and one yellow, had been plopped in front of his dark wood desk, which held a thin desktop monitor and a small, open notebook filled with rows and rows of neat handwriting. I felt slightly overdressed in my tea-length dress with blue roses all over it, but being overdressed was totally on-brand.
A few feet to the right of the desk was a display case filled with books he’d helped publish: Sh*t My Dog Says. Make America Gay Again. I Hope They Serve Fireball in Hell.
My heart sped up as my eyes landed on the last title. The cover featured Marnie Tucker winking at the reader, her arm around a man whose face had been scribbled out. Your face here! yellow text proclaimed over the marks.
I am in New York City. I am in a meeting with Wren Falcon, Marnie Tucker’s agent. Marnie Tucker has millions of readers. I am meeting with Marnie Tucker’s agent. He could be my agent.
“Apologies about this again,” Wren started as I sank down into the yellow beanbag with as much poise as I could muster. The seat was firmer than I’d thought; instead of him looking down at me, we were eye-to-eye. The bright light from the window behind him made Wren appear almost silhouetted. “I don’t have any information about our meeting. Would you mind, ah, giving me the rundown?”
“Sure.” If only he knew that I was there because of a lie! I gave him the one-minute elevator pitch I’d perfected with Oliver, which went something like this: nineteen-year-old Instagram memoirist, Stanford University, redefining art, seven hundred fifty thousand engaged followers. Sometimes, it really paid to have a founder as a best friend.
Wren listened intently before pulling my Instagram up on his computer. He clicked over a few posts, chuckling to himself as he read the latest one, where I’d made Oliver buy me an entire bag of ice at the gas station after I’d jammed my finger while attempting to catch a ball. (This was a true story; I had no hand-eye coordination whatsoever.) I could tell that Wren was impressed; he was making the same faces that Nevaeh had when I’d first shown her my profile.
He kept scrolling, and reading, and scrolling. I sat back and tried to hide the fact that I was taking deep breaths. If he’s looking, it means that he likes it. He’s going to offer you a contract on the spot. Just relax. Don’t overthink it.
Finally, Wren turned back to me. “You’re a fantastic writer,” he started. “Much better than most of my existing clients, honestly. However” — his eyebrows furrowed as he said this — “I’m afraid that I can’t sign you based on your followers alone.”
“What do you mean?” I asked. “Why not?” I didn’t mean to sound bratty, but come on! He’d just said that I was a better writer than most of his existing clients!
“Great writing is only half the battle,” he said gently. “This is going to sound crass, but here, writing is a business. Falcon Ibis needs to sell books, and I’m not positive if thousands of Instagram followers will translate to thousands of buyers.”
“Hundreds of thousands,” I said.
“Right. The point is, I need more assurance that we’ll be able to sell what you write. An audience on a random app doesn’t give me that assurance. Your large social media following is a plus, but it’s not enough of a reason to buy a book. You’ll need coverage in the news. Outlets reporting on you. Real press.”
Unprompted, my mind recalled eating alone in elementary school. Crying in my dark room on my birthday. The empty house that I now spent ninety percent of my time in. My stomach seized up again, but when I spoke, my voice was as steady as ever.
“Got it,” I said, flashing him the smile I usually reserved for pictures. “So if I get my name in the media, you’ll sign me?”
Wren cleared his throat, but I could see that he was fighting back a smile. “If you can translate your Instagram into articles about you — in big-name, respected media platforms — I’ll sign you.”
“Challenge accepted.” I held out my hand.
He shook it with a laugh. “Between you and me, I hope you do come back,” he said. “I have a feeling that you’d do well with us.”
Oh, it was on. I did a full twirl as I exited the building, no longer giving a single fuck about what people on the street thought. My skirt billowed out around me as I spun. I may not have gotten a contract, but in a way, I had something even better: a new milestone.
I would have to prove myself again, but this time, I was ready for it. Baby, let the games begin.