Funding My Dreams Through the Craigslist Gig Page

Photo by Foodie Factor on Unsplash.

It’s a story so classic it’s become cliché: bright eyed young’n moves to NYC with nebulous dreams of art fame, but must secure between one and thirty side hustles to do the actual business of living in the place that Joan Didion once called “the shining, perishable dream itself.” By my mid-twenties, I was that insufferable “art monster”—to quote another, newer New York literary goddess—who could no longer “hack” restaurant jobs, and fast becoming the woman who craved a day job that didn’t necessitate talking to strangers (or, indeed, anyone). I started calling myself a “freelancer” the day I picked up an assignment ghostwriting e-book romance novellas, and never turned back.

That first gig, glorious and ridiculous as it was, briefly lead me to believe I had cracked the independent contractor’s code. “This is so easy,” I bragged to my nonexistent coworkers, while I wrote about “pulsing members” from sunlit coffee shops and cafés. As a ghostwriter, I was able to set my own hours, sock away a modest savings, and—with the help of wiser professionals—even thwack my way through the fire swamp that is doing taxes when you’re self-employed. Plus, there was that whole café thing.

“What is it all these freelancers are complaining about on their message boards?” I wondered, with a hubris that now feels mythic in scope. Then my ghostwriting company abruptly downsized its staff with no real warning or explanation. I got to know the sharp shock that is particular to people who don’t have protective contracts, and the animal fear that seeps in when your days become all about seeking work as opposed to doing it.

A few months went by, during which I wrote blog posts for too little money and temped for too many hours, and the art/day-job balance I’d so enjoyed as a novelist all but disappeared. I felt, more and more, like Joanie D at the end of that same earlier-quoted essay: ready to say goodbye to all that. The dream was perishing. 

Then I remembered that one of my more business-savvy friends had once suggested that, when in doubt, an artist could always find quick, easy money via the Craigslist gig page. “But don’t click on anything asking for models,” he cautioned. “That’s not what it sounds like.” The prospect was surprising. I knew people who found apartments and free couches via the internet’s spin on a stoop, but jobs? Both the Personals and the Gig sections were things I associated with murderers, for no logical reason. “Maybe,” I told the savvy friend. Then I went back to applying for contributor jobs at flagging platforms. No dice.

It took an ill-timed break-up and another client’s dropping me to hear the clarion call of sheer desperation. “Craigslist it is,” I whined to my nonexistent co-workers, at the coffee shops where we now went to fill up our water bottles. And then I clicked on the one “gig” that—God bless and no judgment—did not solicit the privilege of rubbing a stranger’s feet. I went into the murk seeking freedom and under-the-table cash. I went onto the internet to prove to myself that I was still capable of ingenuity, that this city couldn’t eat me and my pretty dreams whole.

When I showed up for my first of two committed days at Undisclosed Corporate Interior Design Startup Trade Show, I was given a company polo shirt, a laconic debriefing on “how to work the espresso machine,” and a pile of boxes. “Everything you need is in there. Feel free to set up your bar how you like it,” I was told, while around me a team of five distracted guys—all with the overeager bearing of startup architects—talked about their mission statement over a souped-up sound system blaring EDM.

The Craigslist post had asked me to demonstrate barista experience, and considering my past life as a café constituent, I’d told the powers that be that I had some. So, in my company polo shirt (“for the trade show purposes, let’s say you just always work for us”) I faced down the single-serving Mr. Coffee, furtively hiding the manual from my employers while I read. It was there that I learned the first rule of gigging with impunity: lie, whenever you can get away with it.

I spent two days in that makeshift bar I set up by myself, during which I mastered the art of making lattes with neither sink nor elbow room. I talked to the startup architects, who would pace the floor in between sparse client appointments and ask me the same questions over and over in a way that was similar to bartending but different. Was I an actor? Did I grow up here? Did I have a boyfriend? I watched a video—also on loop, so approximately one hundred times—that told the origins of this particular Undisclosed Corporate Interior Design Startup in quick cuts and inspirational instrumentals. It was another classic tale: two young friends, one big dream.

After two days of standing and caffeinating in my designated corner, my gig was done. “Stay in touch!” the start-up architects said. (Sweetly, I thought.) One thing that neither anonymous freelancery or service life had ever brought me close to was the particular sincerity of a small business that’s just leaving the dock. These men were so giddy, so gracious, so absurdly ambitious in the way they talked about their company’s future. They had bought hundreds of napkins but the wrong kind of coffee. They had erected a basketball hoop and ordered fancy sandwiches that no one ate. They quoted figures with laughable zeroes, dream profits. Are you an actor? I got asked. A model? What is it that brings you here? Fumbling with beans and sweaty in the borrowed shirt, I watched men in pressed, Fifth Avenue suits clack around the space as the startup architects pitched their many products. That was the moment I realized, with a hubris that now feels insane: these guys are monsters, too. They ache to make their lives on their own stubborn terms, just like me.

I left my two-day trade show stint with a rent-covering check for $350, the phone number of the hired photographer, and two leftover Coronas socked in my purse. I did not say goodbye. Later, I sold the free shirt to Buffalo Exchange for $4.

Writing alone in a room all day is a lonely pursuit, and a little forced interaction can be balm. When I accepted an afternoon’s work “coming up with craft cocktails,” for an “informal neighborhood block party,” I briefly knew the best of both worlds: the social purview of the bar, paired with the safe barrier provided by a kitchen door. I told the appropriate internet people that I was a “cocktail wizard” and then I hopped on the train to Sunset Park, a neighborhood I’d never been to before.

“Here’s what we have,” said a friendly but harried mother of three, pointing to a countertop piled with vodka, gin, tequila, bitters and a pitcher full of what looked like pulpy grapefruit juice. “Feel free to get creative.” I shared the kitchen with two women who prepared fragrant desserts and chattered over my head in Spanish, making faces at my tentative way with the shaker. I felt my stomach lurch with panic. My previous bartending job was at a sports bar. Designing edible cocktails with such motley ingredients was a reach, and there was no manual here.

This gig would require me to dive, the way I dove at my best auditions. I took a deep breath and summoned all the dormant knowledge of my service and consumer life, while putting on a reassuring thespian’s smile. The host and many hostesses were kind. I put the juice over ice, frosted it with triple-sec, made a salt rim, tasted it. Some early guest peeled a glass out of my hand before I’d had time to approve. “Perfect!” he said, smiling, and my heart clicked into place. Lesson two of gigging? Don’t get your panties in a bunch; it’s just cocktails.

Very soon after my “when in doubt just add more booze” revelation, I realized I was being paid to attend a party in a stranger’s home. People chatted. I eavesdropped. It was glorious! At one point, I was given a plate of the desserts I’d been smelling all afternoon and I felt the taste of home in my mouth and went melancholy. What do you do? someone asked. I said I was an actor, but I did a lot of other things, too.

I left that gig with $75 in rent-covering cash, a plate of leftovers, and the smell of someone else’s family clinging to my clothes. A little tipsy, too. Lesson three? Always taste-test. It’s more fun.

I wasn’t making enough money to live on, to be clear. At the peak of my Craigslist gigging, I was filling crucial gaps, while reminding the world—and myself—of all I was willing to do to fund my “real” job. I could be a brand ambassador. An envelope stuffer. I could curate lobby playlists for corporate events. I could sing or play tambourine in a wedding band. I could write “content” for pharmaceutical companies, or stand in Times Square in a bowler hat passing out fliers for Cabaret. I could hang posters and water plants and host unfamiliar dogs in my tiny apartment because I was bold and ingenious enough to do what it took, and because—if I was being perfectly honest—I was getting to enjoy my tourism. One evening’s “gig,” via a friend, found me at a book party at the Neue gallery, nearly hobnobbing with 70s Brooklyn literati ($20/hr). Another put me in a wealthy D.C. politico’s kitchen, sweating over oxtail soup ($100 for the night). Gigging itself could be draining, but the artist in me was intrigued: I was seeing more of the world than I ever had as a bartender or a writer. I was getting stories, and cash. I was learning how to focus on what was in front of me in moments when most of my mental energy was otherwise directed toward where my next meal would come from. I was learning, in short, how to work.

Last Didion reference, I swear: also in “Goodbye To All That,” the patron saint of art monster girls describes her own lean years. “At that time, making a living seemed a game to me, with arbitrary but inflexible rules,” she writes. “I had the feeling that if I needed money I could always get it. I could write a syndicated column for teenagers under the name ‘Debbi Lynn’ or I could smuggle gold into India or I could become a $100 call girl, and none of it would matter.” I know this precise feeling: when the prospect of making enough money to fund bohemia isn’t so much taxing as it is romantic. In a relentlessly ambitious industry, city, and age, the very lucky can afford to think of unconventional money-making as yet one more thing that separates the gritty from the passive, the shrewd from the staid, even the quick from the dead. But the longer I spent trolling Craigslist, I saw it wasn’t so much a testament to What I Was Willing To Sacrifice For Art as it was a new approach to work entirely. I liked the hustle for itself; I liked it separate from art. And I was getting addicted.

I was not really a freelancer before; I see that now. One juicy client does not a “freelancer” make. I believe I became a real freelancer that day at the trade show, or that night in the Sunset Park kitchen, or during those afternoons when I realized I no longer knew how to describe what I did for a living. Was I a writer? An actor? I spent my days in unfamiliar rooms, wearing other people’s shirts and handling other people’s silverware. Which is to say I was acting all the time, and making rent in a dizzy, near-miss kind of way that filled me with a sick adrenaline not unlike stage-fright.

The last lesson of gigging? Know when to leave. In the last two months, two longer-term, stabler hustles have stumped across my transom. I accepted both of these writing gigs with the eagerness of a startup architect, and as the weeks passed I stopped beginning my mornings with a cup of pour-over coffee and the Craigslist gig page. I begin to drift back toward a routine that feels (and is) safe. I write from home and the library. I talk to almost no one during the day. “You must be relieved,” a friend said recently. “I couldn’t do that whole running around thing.”

And I considered. Was I relieved? Not forever, maybe. Not for keeps. But sometimes I think about the tiny, private victory of learning to work a stranger’s espresso machine, or figuring out some ingenious way to scrape adhesive tape off the wall of a middle school (two-day hustle, $14/hr). How curious it was to walk into a strange building for work and know that even if it was terrible in there, I could leave forever in twelve to twenty-four hours. Grateful as I am for stability, I think about the extra $25 I cadged for doing a good job icing lemon tarts as a fill-in caterer and wonder if I’m not just better suited to drifting, to walking the wire. Living was the art, wasn’t it? And what an odd junk cabinet of a life I’d begun, for a minute there. So strange and alive.

I checked the gigs page today, because invoices for proper freelance work are often late and I wanted to pay a credit card bill and go to the movies this weekend. No dice: nothing but feet, for days.

Brittany K. Allen is a Brooklyn-based playwright, prosewright and performer. She has work forthcoming or published in Catapult, The Toast, and Green Mountains Review, among other places.

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