The Blunder in the Ballroom

Ethan Jacobs

© Copyright 2019 by Ethan Jacobs


Photo of large conference.

A few months ago, I nearly emptied out my bank account on travel to and registration for a two-day conference in New York for freelance writers, authors, and journalists. Crazy though such a high-risk purchase may sound, to me, it was a calculated gamble. Having lost track of the number of unsuccessful pitches I had submitted to editors that I was sure would love my work, I figured that if there was something crazy enough to work that I hadn't tried, it was an intercontinental flight to New York to spend two days with the editors I had been unable to convince and a ballroom full of writers who had had better luck. Though a one-on-one encounter with an elusive editor would end in agonizing disaster, what I was able to take away from the conference more than made up for it.

Given my age, the fact that I emptied out my bank account a few months ago should surprise no one--millennials are notoriously impetuous and broke. But while I could have let loose on a quarter-life crisis splurge on a one-way ticket somewhere to “find myself,” I opted for something far less glamorous. I spent my money on a two-day conference for writers, authors, and journalists in New York. In my defense, I didn’t do it on a whim, it was a calculated gamble.

For a while now, I’ve been passionate about writing. In a world that often confuses and intrigues me in equal parts, writing has given me an outlet to seek understanding and find my own voice. In the year leading up to the conference, I had written countless long-form pieces on topics as disparate as why teens love taking unnecessary risks and what made the 1970s such a horrific decade for abuse in the Catholic Church, all in the interest of scratching an itch of curiosity that other mediums couldn’t quite reach.

Yet, for all my zeal, there was one major hurdle I couldn’t quite clear: getting published. Having tried a number of different approaches to pitching and being fairly persistent in my follow-ups with editors, I figured that if there was one thing I hadn’t tried that was crazy enough to work, it was an intercontinental flight to spend two days with the very editors I’d been unable to persuade via email, as well as a cadre of writers who’d had more success.

My work began in earnest months before the conference started. I knew that taking full advantage of the opportunity would require me to do a bit of homework beforehand. A few days after pulling the trigger on the conference’s two-day registration fee and the airfare that would boomerang me from Bogotá to JFK via Mexico City, I tracked down a comprehensive conference schedule.

On paper, I knew I was looking at a rundown of events and workshops for adult writers looking to take the next step in their careers, but I could have been forgiven for mistaking the print-out for an activities list at a children’s summer camp.

There are military dossiers whose meticulousness pale in comparison to the attention to detail that was put into this conference’s schedule. I devised a plan of attack.

In a spreadsheet, I logged the name of every person that would be giving a speaking presentation, hosting a workshop, entertaining pitches from freelance writers, or with whom I had even the slightest chance of rubbing shoulders. I’m sure if I dig deep enough into my notes, I can tell you the preferred flavor of gum of the hotel concierge at the Marriott where the conference was held. I was voracious in finding out as much as I could about everyone that would be there. In the weeks leading up to the conference, it wasn’t uncommon to find me up at 2am, my apartment pitch-black, save for the pale glow of my laptop screen, sleuthing through the catacombs of Linkedin like a noir film private eye.
I made notes about everything, from who’d written what, and for whom, to which J-Schools and writer’s retreats had been most popular among attendees. If someone published a post or produced a podcast, I devoured it. If a presenter had given a talk--or seven--I watched. I tracked the career arcs of more complete strangers than a conspiracy theorist--spooling meters of digital yarn around push pins representing people I might not even meet.

Gradually, I got a feel for who was who and began to prioritize the sessions I wanted to attend based on who would be there. I tried to envision my first encounter with the people I’d researched, double-dutching between “I know who you are” and “I promise, I’m not a stalker,” but the mere simulation of chatting up more accomplished industry peers knotted my stomach.
Enlisting the aid of a smorgasbord of self-help books on networking, small talk, and making the most of chance encounters, I started to compile a list of pointers I could use as a crutch during the conference if needed. I scribbled down goals--what I hoped to get out of the two days and the direction in which I hoped to head professionally afterward--crossed them out, and wrote down new ones. I rifled through Skillshare courses on personal branding and toiled away at an elevator pitch that would boil my quirky writing interests down into something more simple syrup and less Robitussin.

In thinking about how I wanted to present myself to people I was so eager to impress, a troubling thought occurred to me: What if they actually became interested? Having invested so much time preparing so that I could sweep these guys off their feet with my grandiose writing ambitions, I realized I was quickly becoming the proverbial dog that chased the car, unsure what I’d do once I finally caught it.

I glanced back at my inchoate list of goals and realized that simply getting published without learning anything about the industry or improving on my craft wouldn’t do me much good. Imagine how underwhelming Star Wars would have been if Luke just blew up the death star without learning how to use the Force. I scanned the list of conference-goers I’d researched so diligently, having dutifully sorted them into groups with names like “Have to Meet; Kind of Want to Meet; and Meh” corresponding to how precious I thought one-on-one time with them would be. Wanting to make the most of that time, should it come about, I decided to draft a rough list of questions specific to the person to whom they’d be directed, all the while avoiding anything even remotely approximating the “Who do you know?” kind of question that could render me more groupie than aspiring writer.

My plan wasn’t to ask for favors or be introduced to big wigs that could usher me past the velvet rope behind which throngs of writers, myself included, queue up in hopes of getting into the posh nightclub of publication. What I wanted was to absorb as much information as possible from people that had been in my shoes. Meaningful conversations, I reasoned, could turn into meaningful relationships with people that could relate to what I wanted to achieve long-term. That would be way more valuable than a one-off byline.

Research done, priorities set, and questions prepared, I set out for New York, still anxious about making the most of the two days at the conference, but somewhat more confident given the legwork I’d done.

Day one of the conference was a bit of a blur. I spent the better part of it being herded from one room to the next, taking notes in breakout sessions as fast as my wrist would allow, and introducing myself to a handful of fellow attendees, some of whom I was meeting for the first time, others whose backstory I already knew, despite my attempts to pretend otherwise. It felt like I was at a Freshman Orientation whose initiates were all 50-something-year-old white women.

Being an attendee at a conference whose demographic breakdown eerily mirrored that of my mom’s book club had its benefits, though. As a 28-year-old black guy who lives in an exotic-sounding place that few other attendees would have been able to locate on a map, I didn’t have much trouble striking up conversation. Questions about my life and work in Colombia begat broader conversations about the other places I’d lived and worked. That, in turn, proved a handy segue into my interests and the elevator pitch I’d been dreading. My opening up about who I was made others feel more comfortable about doing the same, which gave me an opening to ask follow-up questions that were often along the lines of the ones I’d prepared.

Getting to chat with the “Have to Meet” contingent of attendees proved a bit trickier. If I passed by one of them in the hallway in between sessions, I’d clam up like a junior high school girl approaching her crush. When we did talk, I always seemed to stumble out of the blocks, not sure whether to start by mentioning articles of theirs I’d read or pretend as though I had no idea who they were.

I decided to distance myself (sort of) by sitting in on their workshops rather than going up to them directly. This way, I could be just another person in the crowd. I could soak up everything they had to share and have it look like it was being said at me, even though it felt like it was being said directly to me. Better still, if I wanted to ask a question, I’d look more like a casual audience member you might see during the Q&A portion of an Oprah recording and less like Terry Gross in a Fresh Air interview.

I took my seat toward the back of the room and sat quietly as the panelists worked their way through a presentation peppered with personal anecdotes used to show how they’d gotten to where they are today. The session, “Breaking the Rules and Boosting Your Income,” was designed to make attendees more open-minded about how to earn money from freelance writing and journalism. With underscored points like, “Everyone has superpowers that can be monetized,” the whole thing would have been very on-brand for a Tony Robbins seminar, minus the high-fives and house music.

The time for questions from the audience came as the session began to wind down. There was plenty that I would have loved to have followed up on, but I needed to stick to the plan. I wanted to ask something pointed that would show I’d done my research, but that was also relevant to what had been discussed. By the same token, I knew I couldn’t be too eager to ask the question itself. A fervid hand raise in response to the panelists’ call for questions would make me look like the fourth grade know-it-all desperately seeking recognition from their teacher.

I opted instead for a diffident half-raised index finger as if to say that my question was going to be an inconvenience to the respondent and everyone else in the room.

You gave a TED talk where you referenced Langston Hughes’ poem ‘A Dream Deferred,’ as a metaphor for what happens when you table passion projects that you’re working on, but you just spent the past hour advocating for other, more lucrative work options that may not be in line with our passions. How does a freelancer justify sticking with passion projects that don’t pay?”
The person to whom I’d directed the question nodded politely but seemed unphased. “You have to be able to separate your current project from your main mission,” he remarked. “The nature of being a freelancer is that you’ve sometimes gotta take on projects simply because they pay the bills. You should never lose sight of what you’re passionate about, though.”

Before I was fully able to absorb what had been said, another panelist chimed in. “Make sure you’re setting aside enough time for your moonshot projects,” he advised. “The projects that pay the bills are like drops in the bucket, but the big ticket stuff that seems like a long shot comes from your passion projects.”

I thought back to the months at a time I’d spent pouring over mountains of research papers and peer-reviewed articles as well as the longform pieces they’d helped me write, all ultimately suffering the same fate: unpublished and unread, collecting digital dust in their respective google drive folders like an island of misfit word docs. I never thought about the potential money I could make from anything I wrote because I never wrote anything to make money; I did it because I was interested and wanted to understand a subject better. I realized that they weren’t telling me not to quit my day job, they were telling me to invest free time in passion projects until I could afford to.

I spent the rest of the day floating between the remaining sessions, physically present but mentally stranded in the earlier seminar. The narrative of the gutsy maverick that “gave it all up” or “traded in their 9-5” is such a trope in the canon of success story literature that we hardly ever hear about the people who had to bide their time before realizing their dreams. Also, my year and change of having dedicated myself to writing with little to show for it was like a layover in a slightly below average airport compared to the career purgatory others in my shoes had no doubt found themselves in at one point or another.

As the final session concluded, I made my way out to the lobby, where others had begun to gather for happy hour. Though the day hadn’t been particularly tense, any remnants of formality from stately speeches and stuffy seminars dissolved in the alcohol. People I’d been anxious about approaching at the beginning of the day suddenly no longer scared me. The fanboying sycophant had been replaced by someone who just wanted to chat--it didn’t really matter about what.

Day two began in a vast ballroom where attendees had taken their seats ahead of the conference’s second keynote address. Truthfully, I hadn’t really thought much about it. It certainly wasn’t at the top of my list of talks I needed to attend, nor was its speaker, a highly-successful novelist, someone I’d placed in my “Have to meet” folder. But often you go to these things, thinking you’ll take nothing from them, and wind up getting more out of them than you thought possible.

The speech was ruthlessly efficient in the way only a best-selling author can be. “Five Pillars of Freelance Success,” broken down into bite-sized best practices garnished with a handful of personal anecdotes for good measure. The advice was technical and practical in equal measure. Like any address directed to a room full of aspiring (fill in the blank), it had its obligatory inspirational moments, but was balanced by a healthy dose of realism. “If you want to succeed, you’re going to have to be really persistent,” she warned. “Recognize your specialty and never forget why you’re doing what you’re doing.” It wasn’t quite the “Oh The Places You’ll Go” high school valedictory address, but it definitely checked a lot of the same boxes.

But among the boilerplate bullet points was something special. “Being a successful freelancer requires flexibility,” she began. “Everyone in here has goals, and it’s great to know your destination, but don’t be afraid to use the whole map.” The words shimmered with the mystique and sagacity of an oracle’s prophecy. Everything I’d done over the past few months came rushing back in one forceful Proustian flood. I thought about my destinations--the ones I’d reached and the ones I hadn’t. About what it had taken just to get to New York: physically, using every inch of the map; financially, using every cent I had in my checking account; and mentally, using every ounce of energy remaining at the end of each workday to prepare just for the chance to make a meaningful impression. And as impressive as that was, I realized that so much of the map in my quest to become a better writer was still uncharted. What I’d done up to that point was a great start, but that’s all it was: a start.

The author concluded her address, fielded a few questions, and chatted for a bit with the attendees that approached her afterward. After looking over my notes one last time, I collected my things and exited the ballroom, heading off to the day’s breakout sessions.

If day one had been a Freshman orientation, day two was a condensed syllabus week. With the experience of a day’s-worth of speeches, workshops, and schmoozing under my belt, I didn’t feel the need to attend sessions for novelty’s sake. If a talk looked interesting, I made a note to check it out. By the same token, I promised myself that if it ended up being boring, I wouldn’t force myself to stick around in hopes that it would reveal something Earth-shattering like the credits of an Avengers movie.

I roamed from one workshop to another like a wayward sheep, grazing on information until my gut told me it was time to move on. Though a handful of my peers seemed to share my nomadic zeal, I noticed that many others were foregoing the bulk of the day’s agenda altogether. Holed up in whatever vacant conference room corner or high-backed armchair they could lay claim to, they mouthed what appeared to be rehearsed pitches while skimming over notes in between sips of lukewarm Earl Gray. I scanned the day’s agenda again and immediately remembered what was going on:

Here was the reason people had come from as far as Mexico and Australia for a conference whose duration wasn’t much more than their total travel time. For three hours, attendees would get a chance--a nine-minute tête-à-tête--to sell magazine editors and publishing house reps the very best of what they’d been working on over the past year. As a non-member of the organization sponsoring the conference, I wasn’t allowed to participate. For all intents and purposes, I was a minor, let into the club only to watch the band play, with implied X’s stamped on my hands to make sure I wasn’t given access to anything forbidden. For everyone else, the first day had been mere foreplay; today was the main event.

As the witching hour drew nearer, I was transfixed by the shift in conference atmosphere. Having signed up to volunteer during the attendee/editor check-in, I had a front row seat to the pre-speed dating spectacle brewing in front of the ballroom double doors. The crowd of writers grew larger by the minute, buzzing with excitement like a throng of Black Friday shoppers outside a Best Buy as each lanyard-clad publisher was escorted past them to their respective tables. Though I put on my best poker face, I was just as giddy as they were. I hadn’t mentioned it to anyone, but one of the magazine editors in attendance was at the very top of my conference A-List. I’d read six of her feature-length articles, familiarized myself with the awards she’d received, and even made a footnote or two about her work experience prior to becoming an editor. But I wasn’t going to get to talk to her, at least not outright. Orchestrating an opening was going to take some doing.

As the last of the editors were ushered to their tables, a senior member quieted the crowd of writers. “Is it anyone’s first time at client connections?” she asked, sounding more like a flight attendant addressing exit row passengers than someone whose writing had probably appeared in a seatback magazine. “Don’t be nervous,” she continued, “they’re all excited to meet with you.” She quickly briefed the attendees on the structure of the pitch session, rattled off a few do’s and don'ts and wrapped the spiel in a spirited “NOW WHO’S READY TO GET PAID?!” ribbon as she pushed open the ballroom doors. I half expected the writers to burst through the entrance then and there like a football team barrelling through a taut banner at a pep rally. To my surprise, though, they filed in at a pace whose contained excitement was much more reminiscent of a child who had just been scolded by a lifeguard for running.

Over the next hour, that cycle repeated itself every nine minutes. At one door, a mob of business casual freelancers would assemble anxiously. At another those from the previous session would file out, clutching business cards from editors and publishers like American Idol contestants who’d just been given tickets to Hollywood.

A break in the action finally came around 3:30 and I seized the opportunity to spy on my target. Though I couldn’t see her, I knew where she was seated thanks to a map at the registration table. I’d watched each of the attendees from the previous session file out and, seeing that she hadn’t been among them, knew I’d be able to find her at her table.

With two other senior volunteers guarding the entrance and exit to make sure that unauthorized people like me didn’t go in and pester the guests during their break, I began to scheme. If I just walked in without a reason for doing so, I’d raise suspicion and likely be denied. Instead, I went with something a bit less conspicuous. Grabbing a nearly empty coffee cup I’d used earlier, I got up from the volunteers table, walked up to a slender, middle-aged blonde stationed at one of the doors, and muttered “coffee,” shaking the cup just forcefully enough for her to hear that it was nearly empty. She sized me up with the skepticism of a liquor store cashier examining a fake ID before reluctantly stepping aside.

Making my way to the refreshment table at the rear of the ballroom, I avoided making eye contact with the editor as I passed. It made little difference--she was consumed by work emails. At the rear of the ballroom I peaked over my shoulder as I refilled my cup, simultaneously checking if the lady at the door was watching me and trying to gauge how busy the editor seemed. I stalled for time, pouring milk to the brim of the cup, stirring slowly, and sipping cautiously, like an unsatisfied mixologist.

The faint chime of a bell at the front of the room let me know that the next session would start soon. I walked back the way I’d come, pulling out my phone and manufacturing a series of fake swipes and home screen taps to make myself look busy. A quick glance up revealed I was neither being monitored nor competing with the editor’s phone for attention.

I loved your article about Florida,” I blurted out, grabbing her attention with an involuntary voice crack. “Thanks,” she replied with a bemused smile. “Are you my next meeting?” She’d given me an opening to lie, take a seat across her, and launch into a now refined pitch about who I was, what I’d written, and why my stories were perfect for her magazine. With any luck, I might even pry a business card and an invitation to email her a draft before the blonde kiboshed my ruse. Instead, I froze up. “No, I’m just volunteering. I really like your magazine though,” I stammered. She thanked me again, no less confused than when the conversation started and returned to her emails. The fanboying sycophant had made his triumphant return.

I turned on my heels, sheepishly seeking the exit doors and a rock to crawl under. As I walked out, I looked up just long enough to lock eyes with the blonde, who’d seen the whole thing and was now staring back with more pity than indignation. I spent the remainder of my shift and the lone breakout session that followed it replaying the missed chance from a thousand different vantage points. Though I tried to take notes and remain engaged, all I could think about was how badly I’d blown it. In a last-ditch effort, I abandoned my final breakout session early, hoping to catch the editor in the elevator or lingering in the lobby to chat with a fellow colleague. But when I returned to the scene of the crime, my deepest fears were confirmed: her table was vacant, she was gone.

Shoulders slumped, head hung, and sad Charlie Brown piano melodies on loop in my head, I took refuge at an abandoned sponsor’s table away from where attendees had begun to gather for closing ceremonies. Trying to make sense of it all, I pulled out a large white legal pad I’d been using to take notes and began to journal. Reviewing notes I’d taken from my two days there, I jotted down a few thoughts--smiling about how warmly I’d been received and how much I’d learned in so little time. When I got to the obvious pain point--The Blunder in the Ballroom--I paused. I thought about what had happened--what I’d done and left undone--and laughed to myself, realizing that Eminem had probably written the intro to “Lose Yourself” with people like me in mind:

Look... if you had one shot, or one opportunity to seize everything you ever wanted, in one moment, would you capture it, or just let it slip?

I had let it slip, there was no arguing that. But something in that moment made me parse those lyrics.

Everything you ever wanted” was a bit much. Sure, it was something I hoped for, but I’d only recently begun to work towards it. I thought about how often people fail, the words from the speech I’d heard that morning projecting from the ether like Mufasa’s celestial appeal to Simba: “If you want to succeed, you’re going to have to be really persistent.” I was the last person that needed reminding about how often rejection rears its head for freelance writers. The difference between my case and Eminem’s was that, it wasn’t one shot for me, it was just a shot. There would be others, I thought to myself, many of which I’d probably fail as well. But with any luck, I’d walk out of those the same way I was walking out of the conference: having learned.

My two days in New York didn’t result in any immediate business, nor did it yield me the contact of some über-elusive editor whose bat phone I could dial when I wanted to see my name in print. Nothing worthwhile is ever that easy, and even if it was, having the publishing equivalent of a sugar mama wouldn’t force me to become the writer I someday hope to be. That requires a lot more work, a lot more persistence, and a lot more learning. Unfortunately, it also requires a lot more failure--realizing that the path you thought you could take to reach a goal may not actually get you there. We hardly ever hear about the people that had to bide their time before realizing their dreams, but if there’s anything I learned from New York, it’s that if you know your destination, it’s ok to use the whole map.

Ethan Jacobs is a freelance writer and editor who has worked with clients ranging from burgeoning start-ups to massive multinational corporations. His previous roles have taken him to Kuala Lumpur, Malaysia as a sustainability consultant; South Korea and Brazil as a language instructor; and Colombia, where he currently lives, as an editor and content creator. He is also the creator of Rabbit Holes, a website that publishes long-form articles that take an academic stance in exploring the psychological and sociological explanations behind current events around the globe.   

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