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Living on the Upper East Side, I still traveled back to Minneapolis two, sometimes three, times a month to play a show, give a lecture, or host an event. But making money in the Midwest to spend in Manhattan is hustling backward. The exchange rate is against you; it’s like getting paid in pesos to pay rent in yen. I needed to find a way to start earning in New York.
The process of making a living as a musician in the digital era can be pretty opaque to begin with. The music itself is essentially free—to stream or rip or fileshare. So a lot of musicians try to make the physical album a collectible art object: adding a foldout poster and a bronzed, hand-numbered lock of their own hair.
But the deluxe packaging only goes so far; most pop musicians earn a considerable share of their money from ticket sales on the road. And because no city loves a single musician enough to hear her play every night, the musician has to travel, and travel hard. Every tour stop has to be booked far enough away from the last one that the shows don’t compete with one another. Which means each day, a musician has to drive farther than his or her fans would be willing to. If you stop moving, you die. Just like sharks.
We also make money on merch. We slang T-shirts and bandannas and posters and skeleton-key necklaces and tote bags and shoelaces. Successful merchandising relies on the property of transitivity: a band buys blank unisex T-shirts in bulk, sizes XS through XXXL—garments with no inherent sex appeal whatsoever—and then hires a graphic designer to come up with a screen-printable image that conveys the ethos of the recent album, maybe toss the tour dates on the back. And voilà, the shirt is imbued, transitively, with some of the music’s magic—it’s like swiping the kitchen scissors across a magnet to lend them enough power to lift a paper clip off the countertop. Meanwhile the recorded music itself, which is why anyone cares about the band in the first place, has no role in the economic transaction. Sims, joking in the van, used to describe his occupation as “traveling T-shirt salesman.”
In Minneapolis, I do a lot of posing for pictures. I get recognized at gas stations, restaurants, in the checkout line at Target, and once mid-exam by a gynecology resident. When I came to New York, I knew that only a bit of that equity could make the trip with me.
On the subway headed downtown, very rarely I would catch someone looking at me. Usually it was a young woman. She’d scrutinize my features, my hair, then tap at her phone and look back up. Then she would hold the screen toward me: one of my record covers. If we were close enough to say hello, I’d chat and snap a selfie. If not, I’d smile and mouth, Thank you.
But newly settled in New York, I hadn’t released any music recently, so I didn’t have a product to tour, no new merch. I was living off the last tour’s earnings, some royalties, and odd jobs: the occasional one-off club show, maybe a feature on someone else’s record, a paid speech. In Minnesota, I had a network to keep me busy with those odd jobs. But to build a similar network in New York the same way I’d done it at home—selling CDs out of my backpack and passing out flyers at clubs—would take another lifetime.
I went to shows in Harlem, struck up conversation with any purposeful-looking stranger. I handed out my number to anyone who claimed to work in the entertainment industry. I wrote down the Instagram handles of the good performers who played in the subway, thinking maybe I could assemble a band that way, might make an interesting backstory. I weirded out musicians at their own club gigs, trying to convince them that I was a credible professional—which cannot be effectively communicated by yelling I am a credible professional over house music.
Halfway through my lease, I was sleeping in New York, but still essentially commuting to Minneapolis. The groceries were expensive and the apartment was small and dim—I hadn’t even realized it was north-facing until after I’d moved in. To try and get a little light, I set a makeup mirror on the cement ledge outside my kitchen window and angled it to shoot a ray of sun inside. Where that ray hit the wall, I hung a second mirror, hoping to create some sort of overhead laser maze of natural light. I went to bed early, wrote, drank white wine, cooked, adjusted my mirrors. I was going stir-crazy and feeling the money evaporate. But my anxiety wasn’t really about the money; I’ve always been a saver and I had enough in the bank to weather a long run of rainy days. It was about pride, and purpose. If I couldn’t find work in the city, then moving to New York was nothing more than running away from home—a grown-up on a plane with her lunch box and her roller skates.
Working in the music industry is not like hunting, where you set your sights on a large target and take careful aim. It’s more like trapping, where you set a hundred lines with bait and bells, ready to run toward the first sign of action. After half a year in New York, a few bells started to ring. First, I met a guy named Sxip who wrote Jank, which I think is a term he coined for central eastern European circus music. He performed in winter-white suits, playing hand bells and pennywhistles pitched down to sound like a cathedral organ, often in foreign, woozy scales. Amanda Palmer had introduced us casually on Twitter, but both of us happened to stumble into the other’s work unawares—he picked up my chapbook at an indie bookstore on a whim, and I stumbled across one of his free outdoor shows in Harlem. He invited me to appear as a guest performer at a showcase in Brooklyn and I read a poem I’d written called “Tits on the Moon.” He paid me a hundred bucks and I exchanged contact information with a few of the other guest performers.
Then Matthew Santos called. He was a friend from the Midwest coming through New York on tour. He invited me to rap an eight-bar verse at a fancy hotel party. No money, but free drinks, maybe some good networking. I stood in the cramped basement party, casually eating all of the hors d’oeuvres. When I was called to the front of the room, the man at the piano was Jon Batiste, musical director of The Late Show with Stephen Colbert. I was the third rapper to perform. I don’t look like an emcee, particularly in a cowl-neck sweater and a cheekful of appetizers, but that adds an element of surprise that can work to my advantage—a Claire Kent effect. After my verse, a videographer documenting the event rushed up to trade numbers; the booker liked me and took my contact for future shows. Jon Batiste, still playing piano, quietly said “Nice raps” over his shoulder.
Sxip hired me again, this time for a circus gig that flew me to LA. The makeup artist made me look like a porcelain Victorian doll and I performed alongside Sxip in a gilded theater full of mirrors and chandeliers. There was a handsome French-speaking acrobat; two almost-naked dancers doing a routine of impossible lifts that had been designed by Madonna’s choreographer; and a dimpled sword swallower named Heather who slid a neon tube down her throat that glowed right through her windpipe. Sxip was accustomed to the circus bit; he’d toured with the troupe for years, but I kept yelling “Wow!” like an idiot at rehearsals.
Then Lin-Manuel called.
Lin-Manuel Miranda is the musician, actor, and playwright who wrote the musical Hamilton. It is impossible to overstate the extent to which that play permeated New York culture. At the gym, he was on the cover of GQ; on WNYC, the pledge drivers wooed donors with the possibility of winning tickets; online, Michelle Obama said it was one of the best works of art in any genre; on TV, Miranda hosted SNL. But even more incredible was how many times the word Hamilton was said on the street; that word rang out in coffee shops, on the train, in cell phone conversations. In Minneapolis, I’d never seen a piece of art take over the public consciousness in that way. It was one topic of which everyone seemed to be aware and could offer some comment—like weather, or war.
I first heard of Hamilton when I was still living in Minneapolis. The production had been running for less than a year then and, while celebrated, it hadn’t gone supernova. (Or maybe it had, but Minnesota was still waiting for the shockwave to travel overland from Broadway.) Someone told me that one of my songs, a track called “Dixon’s Girl,” had been included in an online playlist curated by Lin-Manuel. So I looked him up on Twitter to say hello, figuring maybe I could roll through to catch the play next time I was in New York. (In retrospect, of course, this is ridiculous. Those tickets were impossible to get at almost any price. But I was an innocent and Lin lived up to his reputation as an easy-going, likable guy with a breezy charm and generous disposition.) He made arrangements for me to see the play, and although I’d been prepared to be impressed—by the singing, the dancing, the catchy compositions—the tragic romance of the storyline blindsided me. I wept into the sleeve of my sweater, trying to hide my tears from my little cousin, who I’d taken as my guest.
I had met with Lin a few times since then, texted on occasion, but we hadn’t spoken on the phone. I picked up his call immediately, my side of the conversation echoing off the walls of my apartment. Lin asked if I’d be game to cover a song for The Hamilton Mixtape. At that point, the other artists publicly confirmed for the project included John Legend, Alicia Keys, and Questlove. The song was called “Congratulations,” he said. It hadn’t been featured in the musical, but he could send sheet music and a link to a live performance by Renée Elise Goldsberry, the actress who’d played Angelica on Broadway. Lin was in a car, running between events. He said he’d send an email with details.
I hung up and did a touchdown dance in my apartment. Pacing, I sent texts to musician friends to assemble my team. Jessy Greene could record violin from her house in LA. Andy Thompson, a composer and multi-instrumentalist, could run point on an arrangement. Lazerbeak was game to help with production. Andy enlisted a couple of other players and Lazerbeak said he’d start digging for sounds to craft a percussion treatment. Over the next couple of months, we could pull together something awesome.
When I got the email from Lin’s team, the song was due in six days.
Within thirty hours, string players were recording parts in their home studios. I flew back to Minneapolis, where Andy Thompson had been working nonstop out of his basement. Lazerbeak came over and opened his laptop on his knees. I tracked vocals standing barefoot on Andy’s carpet. I struggled with the high note, tried again, then again. (How can these Broadway dudes hit this shit while dancing in corsets?) On Andy’s urging I sang louder than I was used to doing; my pitch wandered all over the place as I strained to project. Andy’s voice through my headphones encouraged me to push: That’s great, just gotta get on top of it. The final takes sounded strange to me—my instrument, played by someone else.
We took a break for dinner and I bought Andy’s kids pizza. To our collective surprise (and my concern), one of Andy’s five-year-old sons ate as much as six-foot-two Lazerbeak. I waited, but no one threw up. We wrapped for the night, leaving Andy to mix.
“Congratulations” is sung from the perspective of a woman who has spent many years in love with a man she can’t have. Although she’s moved far away, she still pines for his affection, and is exasperated by his infidelities. It seemed I was destined to sing torch songs to difficult men, even at a 250-year remove. I did a convincing cover.
I submitted the finished product to Lin and his team at Atlantic. Then I got busy with digital housekeeping. The release date was just a couple of months away. When the mixtape dropped, I wanted it to be easy for new fans to find me, listen to my work, and connect with me directly on social platforms. With help from the Doomtree team, and a couple of industry friends, I set to work updating my profiles on the streaming sites. (God, was Spotify still using the photo with long hair? People might not even know that that’s the same person. And why can’t iTunes separate my discography from the work of the other Dessa—a Filipina singer who seems to perform primarily at patriotic events or on sun-soaked beaches? I could only presume that she was similarly exasperated, that her fans were confused to find English-language hip-hop where they’d hoped to find the Philippine national anthem. If I ever meet Dessa, we are doing a shot together, toasting in our respective languages, and then marching on Apple HQ until someone acknowledges that we are different people.)
On the Friday the mixtape dropped, I gave in to the self-obsessed, Gollum-y behaviors that musicians don’t like to admit to. Phone in hand, I clicked Refresh for hours, reading comments, counting likes. As midnight hit in time zone after time zone, the release date swept around the world. Theater kids in dozens of countries pressed Play as soon as their preorders were digitally delivered and then they lost their minds in unison. I received emails from close friends and distant colleagues with Congratulations! as the subject line and Congratulations! as the body of the message. Jaclyn, knowing my propensity to worry about rain on parade days, wrote, “I hope you’re basking.” The Nuyorican side of my family started a text thread to share links, exclamation marks, and emojis and complain that the song was too short.
The mixtape hit number one on the Billboard charts the first week. Soon, “Congratulations” had been streamed over a million times and was listed by several media outlets as one of the standout tracks on the record. (That fact is probably due in part to the fact that the song had been cut from the original production. Fans were excited to hear a new composition from Lin and his collaborators.)
Once or twice, Lazerbeak and I allowed ourselves to ask each other, Could this, like, go gold? Then we’d change the subject immediately; speculation of that sort is indelicate and, historically, an invitation for disappointment. Most indie musicians have a litany of “almosts”: the major label deal that didn’t quite come through; the high-buck movie placement license that dissolved at the last minute, the rainstorm that canceled the whole festival.
In the end, the song didn’t bring as much traffic to my music as I’d hoped. When Lazerbeak and I pulled my sales numbers, the bump was really almost negligible. The additional revenue was so insignificant I joked to Lazerbeak that I was going to celebrate by splurging on a one-way ticket to Cleveland.
But the song did give me a calling card I could use in New York. With the mixtape on my résumé, every professional introduction got easier. I was a credible professional. I managed to secure a month-long artist residency gig at WNYC (with the help from a producer friend back home) and sold out every show. amNewYork publicized the series with a long interview. My neighbor across the hall stopped me on her way out of the building to say, Hey, I saw your picture in the paper! The mixtape wasn’t a magic bullet, but it bought me a few extra seconds of consideration from every decision maker I was hoping to persuade.
There aren’t many big breaks in music. But I’d spent all my years with Doomtree learning how to work the hairline fractures; a little leverage was all I needed.
My career was starting to rise to the same relative heights as X’s. And however complicated my feelings for him, I made a pledge to myself that if I could help him somehow as a musician, I would. He’d pulled me up and along when it would have been easier to help almost anyone else. Now I was making my own way, on my own steam, and might have the chance to return the favor.
If you can make it there, you can make it anywhere—it’s a phrase too cute to be true, a souvenir from an era when smoking was still healthy. (My favorite turn on the expression actually flips it to refer to New Orleans: If you can’t make it here, you can’t make it anywhere.) But hyperbole aside, New York is a big, expensive city, stocked with world-class talent, ambition, and determination. And I had found a foothold, dammit. I might’ve come to New York to escape, but I was more than just a runaway.