As I grabbed a soda from the bar after my set, an older man struck up a conversation. I told him I was touring the country by bus, train, and plane, with a guitar and a bag. He said, “I wish I’d done that when I was your age.” A few hours later, at the other show, he asked, “Do you have any records for sale?” I had none, and I was all out of tapes, but if he’d Venmo me 10 dollars, I’d send him a link to download my new album. “Yeah, I’ve heard that one before,” he said.
Someone on a plane will ask: “What’s your name? Maybe I’ve heard of you.” A date says, “You look like a musician,” or, “You kinda give me a Hozier vibe.” Catch up with an acquaintance and they tell you you’re “famous.” It’s hard to know how to respond to well-intentioned remarks like these. Surely, the point of working as a musician isn’t fame or keeping up appearances.
Admittedly, many aspects of the so-called music industry are built on houses of cards. Once-independent venues, booking agencies, websites, and record labels consolidate with corporations or go defunct; those outlets that remain treat superstars not as corporate commodities but auteurs, while viewing independent working musicians with performative skepticism. Other resources remain gatekept from artists slogging in obscurity. Grammy-nominated touring artists sell out countless shows and come home tens of thousands of dollars in debt, revenue disappearing either through the sheer multifaceted complication of producing albums or tours, or into the pockets of corporations and empty suits. Independent label executives brag, in private, about cheating artists out of advances. So artists have to get their money elsewhere: they make TikToks complaining about how stupid and pointless it is to make TikToks; they mint music into NFTs as if doing so will make their work more accessible outside of a moneyed set of digital half-patrons; they post GoFundMes to cover healthcare costs or make rent.
The prevailing wisdom says that, for a young musician, touring is necessary and good, something of an antidote to the rapidly spiraling madness of American life. Perhaps, when artists treat the creative process as inherently mystical and guard the workings of their creative careers with secrecy, it makes sense that nonmusicians would regard these artists as zoo animals. Yet, the longer I’ve been able to work as a musician, the more playing music has become — no matter how rarefied a musician or precarious their position may seem — not exclusive, not the province of privilege, but simply another kind of work. And, as George Eliot writes, “the merely egoistic satisfactions of fame are easily nullified by toothache.”
I grew up in a musical household in Houston. My mom played flute and piccolo. My dad plays casual guitar. I remember dancing to Praetorius in the small living room of my family home; improvising timid harmonies at a singing camp and running, in tears, into the arms of my mother; writing short songs in my head that inadvertently cribbed Beatles guitar solos; tapping drum parts on my thighs in the back of the car. In elementary school, I learned piano songs written for students, with names like “Groovin’”; in middle school, I ping-ponged between studying cerebral 1940s clarinet études and playing half-baked pop song arrangements at pep rallies. At night, I fantasized about playing arenas with my best friends, my crushes forming a coterie of groupies in the front row. At school, I wore my lanyard around my neck.
Once I hit ninth grade, I did little outside of schoolwork besides listening to music and teaching myself guitar. I dreamed of putting out records on respected labels and touring behind them, even though these things seemed unachievable without knowledge, deep pockets, recording equipment, connections, or anyone in my life who could relate to that desire. I bounced between a series of cheap starter guitars, some of which dated back to my dad’s young adulthood. Then I won one in a contest. As my listening diet — and depression — grew, I stumbled upon solo guitarists touring the world and putting out records: Steve Gunn, Daniel Bachman, Nathan Salsburg, Michael Chapman, Jack Rose. There were a few common threads: they generally studied their instrument on their own, without receiving formal training in a given idiom; they didn’t rely on gimmicks to write songs; they didn’t put on airs or costumes; and they often played instrumental music. Around the same time, I dove deep into bands like Unwound, Fugazi, and the Minutemen, and reveled in the ethical principles that informed their tours and music. Putting these together, I had a roadmap. It was a revelation. For the first time, I felt like I could do it too.
In a high school band, I desecrated alt-rock songs. I began playing solo concerts of other people’s music. For my first show, I told the venue I’d play for free. I played a series of coffee-shop tip gigs with no one listening. My modest goals grew to playing concerts at venues that updated their event calendars. At tremendously sad Houston dive bars, I shared local bills so baffling they removed one’s capacity for pity. At least once, a headliner called me the “high school opener.” In a stroke of unluck, my first tour looped from Dallas to Houston roughly two weeks after Hurricane Harvey made landfall. My tourmates and I gritted our teeth through three horrific gigs whose audiences totaled to two handfuls. One night I was smooth-talking a barista into giving me a free sandwich, because “I don’t drink coffee” (true); the next I was struggling to avoid cursing out a coffee shop for not paying us after hours of playing. The next summer, I spent nearly a month on the road in an SUV crammed between acoustic instruments and travel necessities. My tourmates and I traveled for two weeks up the East Coast, followed by a poorly routed mad dash back to Texas via Massachusetts and the Midwest. I messaged friends each time I confirmed a concert. Our shows vacillated between low turnout and packed houses, our quarters between couches, floors, soggy tents, and the occasional bed.
I knew little of what I was doing. But with each performance, I felt more of the quiet conviction that I was doing something right. I hardly tallied my income and expenses; I was foolish, and it felt beside the point. I wasn’t making a living yet. Perhaps this is obvious to you. Nor did I think it odd when my friends would squeeze in remote work from the road (which I do myself), or tour around sick days, vacations, odd jobs, and unemployment. For years, the most money I’d made off of one proper concert was 50 dollars. I felt rich.
Over the past seven and a half years, I’ve played about 215 shows in the United States and Europe, from the most secret spaces of the underground to the most famous festivals in the world. Unlike most artists in such a position, I’ve booked almost every one of those shows on my own. I’ve mainly toured in support of five albums of instrumental guitar music — music that veers between being immediate and abstract, condensed and sprawling — sometimes solo, sometimes in duos, sometimes leading a band if the money is there. By and large, my collaborators are close friends. My shows are not expensive to produce. I am my own almost everything.
I approach performances a bit differently from most. I don’t use setlists during my concerts. I improvise in the interstitial spaces of my music and occasionally play entirely improvised sets. I generally don’t process my guitar with pedals, and often borrow amps or instruments. Musicians, understandably, often try to control these variables. More often than not, I embrace them. It’s a marked contrast from those musicians whose concerts manage preplanned sonic elements with precision; whose main instrument is a computer; who work directly within the traditional infrastructures of classical, folk, or jazz musics; or whose songs have words, or who sing at all.
If I play a solo acoustic set — in which case I ask to use one microphone for my guitar and another microphone to talk — my music has about as little mediation as possible between what I do and what the audience hears. In spite of its directness, it can be difficult to categorize. I try to take advantage of this. On my most recent tour, I shared bills with an Americana singer, an acclaimed ambient musician, an intergenerational and interracial free jazz group, and a kora player. Country, noise, traditional, laptops.
I’ve been lucky that record labels and music writers have been able to make my music make sense for others. Small record labels, often run by one person, have released limited-edition LPs. These, rather than T-shirts or tote bags, are my main currency on the road, each record a tangible marker to accompany an intangible experience. By the time I’m selling them, I’ve played a show and talked with its promoter for months — sometimes years — to book it.
Right now, to book a show in the United States, I’ll introduce myself over email to a music venue or concert promoter, suggest a date, and share links to my latest album and some press coverage, plus a couple of quick paragraphs describing my music and myself as if I didn’t write them. The goal is to make it as easy as possible for the person on the other side to say yes, even if they have no idea who you are or what you do, and even if it means toggling between first and third person: I was wondering if you’d like to have Eli Winter (that’s me) …
I usually send a few such emails per city. Sometimes I send a few messages over the social-media lazy Susan. I follow up, check back, circle back, nudge. I attempt to track this in a spreadsheet, but there are just enough tabs, all information-dense enough, that my eyes glaze over. In Europe, I’ve been able to work with agents — who do this work for a commission — but thus far their work has been limited to a few countries, leaving me to search for many gigs on my own. Sometimes, after months of work on a single string of dates, I throw my hands up. To even get to this point has taken me seven years of playing shows and the help of several friends. At best, it’s rewarding. At worst, it’s skipping stones on a dry riverbed.
Even after a tour is booked, you have to keep pitching yourself. You try to convince strangers that your music is worthwhile, and that you need food to eat, and will they please give you 10 dollars for a tape so you can buy a cheap sandwich in an expensive city. Or you ask another set of strangers to let you play their two-bit cafe for tips on a Thursday, and also you’re doing this over Instagram DMs. Sending promotional copies of your music to spreadsheets full of strangers, hoping a handful of writers might listen and one write about it. Getting up at 4:45 a.m. to catch five trains in 12 hours and arriving three hours before you’re supposed to — or arriving so late that you show up to your own gig two hours after it started. Getting from show to show without losing your phone, going broke, or getting hit by a bus. Protecting your instruments and yourself. Maintaining healthy relationships with bandmates if you have them; maintaining a healthy, at least somewhat active lifestyle amidst grueling travel and the temptations of gas-station roller hot dogs; avoiding COVID-19, injury, and other illness; playing a show, working oneself into froth, getting up the next day, traveling to the next venue, and doing it again. Squeeze in remote work while on tour (I do), or add alcohol or substances to the mix (I don’t), and these varied stresses accumulate all the more. A lot of my lifestyle involves mitigating this stress.
Still, the thought of going on tour and sustaining this work produces an undercurrent of excitement that moves beyond the reach of words. Sometimes I wonder if I’m wrong to feel this way, wrong to carry on. Sure — touring has changed my life, deepened its meaning, made me a kinder person who is more open and assertive, strengthened my resolve. It’s taken me to parts of the country and world I’d otherwise not be able to visit, and it’s given me experiences I would otherwise never have had and communities of friends around the world. But it’s hard not to notice that artists with the gigs I can only dream of air grievances with the indignities of playing those gigs, or that more and more musicians who play them might pivot to the postal service or coding or pop-up kitchens.
The first thing people told me was to get a car. Get a decent car, get a beater, get a van — learn to drive. I haven’t.
Part of the trouble is that expenses scale up. A car is cheaper than a van, which is cheaper than a bus, which is cheaper than a tour bus, which is cheaper than a jet. Covering not just expenses but also repairs for these adds up fast. A solo artist’s bandmates are employees of that artist, as are any other members of an artist’s touring party, all of whom need some amount of money per night, plus accommodations. If you want to add visual elements to the music, it’ll cost you, as it will if you have merchandise shipped to a venue in your care, or if you’re paying back an advance from a record label. Cross international borders and expenses compound. Through no fault of their own, a touring artist could start a tour in the hole and end it deeper still.
The broad strokes of how touring solo works for me right now: I leave my apartment in Chicago, with an electric guitar and a few tote bags of records and necessaries, to catch a train. (Most recently, a 19-hour trip to Philadelphia, with a two-hour layover in Pittsburgh at five in the morning.) For the majority of this time, including when I sleep, I’ll wear a KN95 mask, which I find easier for long-term use than an N95.
Once my train arrives in, say, Philly, I may have an hour to get to the appointed venue for the night’s concert. I’ll play a set of instrumental guitar music for 40 minutes or so (masked), hawk records to concertgoers and gently wheedle them into joining my email list (masked), sleep for a few hours on a couch a kind friend has offered me (masked); in the morning, if I’m lucky, I’ll shower, then hop on the train (masked) and do it again, and again, and again. Last year, touring Europe for the first time, the scholar and multi-instrumentalist Cameron Knowler and I ran through this routine every day for a month. (Here I must note that Cameron, a dear friend, saved my life four times during one week in the United Kingdom — ah, street crossings.)
Usually, I try to squeeze in as many concerts as possible, but every so often, I’ll have an off day. Last November, touring the East Coast, I had twice as many off days as concerts. If I travel with a band, I’ll swap train travel with a rented minivan from a car-sharing app, paying all the travel expenses and finding good, cheap food from the backseat. But, more often than not, the stresses, exhaustion, and danger of driving substitute themselves for the relative inconveniences of microwavable cheeseburgers in steam bags. Bands touring in cars will lug their gear several times a day: drums, instruments, massive amps, boxes of LPs or T-shirts or posters or arcane boutique objects. I’m limited to what I can carry in one trip.
It’s not like my way is always convenient. Sometimes I feel like I’m making it harder on myself or worry that my tourmates are plotting revenge. But when I first told a working musician friend I was touring by bus and train, he said, “That’s great, you’ll save a lot of money on gas.” Over four dates in the Midwest leading a trio last fall, after covering expenses and paying my bandmates, I made about a seventh of what I could expect to make were the same tour expenses adjusted for solo performances: roughly 250 bucks. I could pay my bandmates, the tour made money, nothing went wrong: I was happy.
The question sometimes comes up: “Don’t you think you should be making more money?” It’s hard to argue against the point. But I don’t think it’s a reason to stop.
A musician might argue that music is subject to “the market” like any other kind of commercialized good, and that no one is owed a living for it. To presume “the market” is inherently natural is to sidestep the artifice on which it and every “market” is built, and to take one’s own struggles as not only inevitable but also righteous. I suffered; so should you, because the system is designed to make us suffer.
Most working artists — and that’s what musicians are: freelancers by a different name — move through boom or bust periods in their finances and ability to produce work. If these are your conditions, and you live without independent wealth or some sort of safety net, one of the keys is to avail oneself as a resource and help your friends and peers as much as possible, rather than atomize yourself and buy into the narcissism of small differences. Another key is to live as frugally as possible. I try to do both.
I live with roommates who are also musicians in an apartment. I’m a cis white man; thanks to financial aid, scholarships, and a now obsolete Texas college payment program, I graduated from a private university without student loan debt. I apply for grants to give my creative work a financial cushion. I work remotely, so I can work on the road as needed. I also keep a pot filled on my bedroom radiator, compare offal prices at local groceries, use a hand-me-down pair of headphones with a duct-taped left ear, and own one pair of shoes. I take public transit, bum rides, or walk. Several friends have given me articles of clothing apropos of nothing. I’ve known musicians who have lived off of trust funds and bought houses with them while cosplaying poverty, and musicians who are unfairly indebted and struggle to pay basic expenses yet give what money they have to people who need it.
From the start of 2020 to the pandemic’s onset that March, I was sketching and booking three consecutive carless tours split between the continental United States and Europe, working in the spare moments I had as a full-time student. Some nights I crawled into bed and woke up just in time to run to my BA thesis workshop. Several pieces of the European puzzle — exceedingly difficult to book without a connected agent — were about to fall into place when lockdown started. I had never worked quite so hard on something that couldn’t happen. I didn’t know what to do or how to grieve, and I found it difficult to know how to move forward in my life without the project that had served as the engine for so much of its recent progress.
Touring safely during the pandemic has felt like a contradiction in terms. If you get COVID-19 on tour, you lose hundreds, if not thousands, of dollars. There’s no way around it. I can afford to front the cost not just because my overhead is relatively low, but because I expect to make it back. How I’ve managed to avoid catching coronavirus on the road, despite the obvious risk, I can’t say. I often play while wearing a mask and often ask audience members to wear masks from the stage. When possible, I play outside or require masks among attendees and, at least once a tour, stream in-person shows online or provide audio after the fact. Sometimes I wear masks for the better part of 30 hours straight. This past year, I’ve worn them so regularly, for so long, that the backs of my ears are scarring. It’s difficult to manage such precautions in the effective absence of public health, whether for a crowd or myself, and even more difficult to know if I’m doing it effectively.
Every gig is another turn of Russian roulette. And I don’t know how to reconcile my love for touring, the mountains of growth it has brought my life, with the knowledge that it could lead to my undoing — if not by illness, then by design.
Halfway into my last concert of 2022, in Brooklyn, I found myself screaming through my mask while I played. I was performing a song called “Dayenu,” which translates loosely from Hebrew as “It would have been enough,” in memory of jaimie branch, who plays on the studio recording, and who died suddenly two days after it came out, a few months before the show. Because Fennesz, a well-known guitarist who works with electronics, was in town from Austria, the show was sold out; by chance, Maria BC, a friend whose music I’m enamored with, was also playing. I had already seen them play four times that year. Here, playing as a trio with Nell Sather and Noa Sauer, their music was characteristically luminous, their presentation characteristically poised. I wanted to do right by them, Fennesz, the promoters, the audience.
The relative comfort I now feel onstage, inhabiting a performance or bantering between songs, comes from exposure therapy: accepting my toolkit, learning what tools can help me access that comfort, and refining it through gig after gig after gig. Still, sometimes, I’m out of my mind and have no earthly idea what I’m saying or why I, an introvert with a history of social anxiety, should be center-stage. Though I typically play seated, I often move around; sometimes the music carries me out of my seat, makes me stomp my foot so hard it distracts my bandmates. At some shows, you lose control of the reins, or feel like you have, so even if you play well, the feeling is tantamount to it happening. Which is exactly what I thought was happening in Brooklyn.
I feel obligated to remember my friend, who lived south of the night’s venue and often played there, and I regularly play “Dayenu” in her memory. Some nights, I can barely get the words out: “in memory of.” This night was particularly hard. Perhaps this scream was some manifestation of grief. My first thought was the nature of the thing: I’ve never screamed during a set before. Then, the optics: If the crowd sees my mask beneath my nose I’ll feel like a fool, and if I have to scream during my set, it should sound better than this, and should I be wearing a mask now at all? I tucked my head behind my guitar. I kept playing. I screamed two more times. Once offstage, I spent the rest of the night in a haze, attempting to comprehend my performance and the kind well-wishers who told me I did great.
Even the best of settings night after night can make your chest snap. Tom Petty and Prince died from taking painkillers to manage touring, Emily Remler on tour in Australia, Mark Sandman of a heart attack onstage, Johnny Dyani after playing a gig, which makes me wonder if any number of my friends or I are bound for the same, if the rigors of the endeavor we love will expedite our demise.
Eli Winter is a musician and writer based in Chicago.