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Parker Beesley sat with his guitar in hand surrounded by fellow musicians — some he knew, some he didn’t, and a few made him feel like a starstruck teenager.
“Do you know this tune?”
Parker did a double take. He arrived at the jam with his guitar, prepared to play. But he wasn’t prepared for Jon Gordon, a world class alto-sax player, to put him on the spot. He gripped the neck of his guitar tightly.
“Well?” said Gordon, his brushed, matte brass alto saxophone reflecting the dim lights.
“No, I don’t know it at all.”
“Can you figure it out?”
“Sure, why not,” Parker said, hoping it was true. It can’t be that hard, he thought. It’s just a Monk tune. He pinched his guitar between his upper right arm and chest and pulled out his phone to find the chart. It can’t be that hard. He typed “Ask Me Now” by Thelonius Monk into iReal. The app pulled up a chart for him with the chord changes.
I’m fucked, he said to himself. The room seemed to shrink, and the air was suddenly a little too thin. I’m fucked. There’s no way. I’m going to sound horrible on this and Jon Gordon is going to hate me forever.
There wasn’t time for Parker to wallow in the sudden, unexpected death of his music career, because Gordon just started to play. The wall of sound hit Parker in the face and left him stunned for a moment. No count? He’s just going. Is everyone else hearing this? Nobody else seemed fazed.
Gordon was standing barely a foot away from Parker — closer than he’d ever been. Parker’s knees wobbled, barely holding him up as the tune built to a crescendo and the solo section began. In that moment, Parker thought Jon Gordon might be the most beautiful person he had ever seen. This is what it feels like when you see the person you love and know you’re going to marry them, he thought. It wasn’t love in the romantic sense, but in the way only music can make you feel so deeply. Then, as Parker was melting in the sound, sure he would never leave it, Gordon cued the downbeat. He only had time to think to himself, what the fuck? Then he joined in.

Parker Beesley, 19, who is in his second year of jazz guitar at the University of Manitoba Desautels Faculty of Music, says playing with Jon Gordon was an important moment for him.
“That moment, to me, that’s everything I want to be as a player,” he said. “When you play with people like that, it gives you all the inspiration you need to go and practice for eight hours.”
In addition to being a student, Beesley is an independent musician who plays shows around Winnipeg two to three times a month.
What is Independent Music?
The term ‘indie’ music might conjure up a certain image and sound: jangling guitars, straight-ahead drums, or a funky beat, and slightly out-of-tune vocals combined with wild hair, bold fashion choices and a stick-it-to-the-man sentiment. Everyone’s image may be different, but it probably shares one characteristic — art over fame. To be an indie music fan is to root for the underdog. Yet, their cult-like followings often spring young, unprepared musicians into stardom. Some of the world’s biggest bands are or were independent: Nirvana, Arctic Monkeys, The Strokes, The Cure, The Smiths, Pixies.
Though indie music has taken on a definition of its own, independent music has a clear definition: if you’re not represented by a major label, no matter the genre, you’re independent. There are three major labels today: Universal Music Group, Sony Music Entertainment, and Warner Music Group. In Q1 of 2024, their digital revenue market shares added up to 76.79 per cent, with independent labels making up the other 23.21 per cent, according to an article by Billboard.
Almost everyone starts out as independent. Then, a chosen few get noticed by a major label and sign with them. Labels take anywhere from 50 to 90 per cent of what artists make. They use some of that money to fund services and make financial investments in artists.
Music production, song writing, marketing, video production, concert production, concert promotion, tour organization, legal representation: there are countless moving parts in a musician’s career. When the money is small, artists can manage these things on their own. But when their rockstar dreams come true, it becomes nearly impossible. Labels can help artists keep their head above water by managing these things for them.
So, why stay independent?
Independent doesn’t mean unsigned — independent musicians can be signed to a label, just not a major label or any of their subsidiaries. Individual small, independent labels take up a very small percentage of the market on their own, but when added together they rival the large companies.
Major labels are good at making money and cultivating a following, and since signing an artist is an investment, labels want to maximize their return, so they want a say in the creative process and output. While signing with a big label has huge benefits, including financially, artists that stay independent often maintain more creative control. Alongside this creative freedom is the need to make a living.
Making Money
Independent musicians usually have multiple sources of income. Many artists work gig-to-gig and get hired through networking. Gigs, studio work, production, and teaching are all common sources of income, but work can be inconsistent and artists often diversify their income stream.
Lindsay Woolger is a Winnipeg-based bassist, music teacher, and part-time shoemaker. Shoe repair isn’t her greatest passion, but it’s consistent, flexible work. She can take time off to pursue music opportunities, and when music work is thin, she works more hours at The Leather Patch.
“I can bail on that job… no one is gonna lose an arm,” she said.
Woolger says she could survive without her shoe-repair gig, but the extra income lets her be more selective in the music jobs she takes.
“I find taking music work that I don’t want to do is hard on my soul, it’s hard on my spirit and it makes me, like, question my whole life,” she said.
She also says working with her hands is nice because it flexes the same mental and physical muscles she uses in her music.
Woolger also works for Sistema Winnipeg, a youth string instrument education program created by the Winnipeg Symphony Orchestra. She teaches cello at Elwick Community School.
“Which is funny, because I’m a bass player,” she said.
She teaches for two and a half hours, five days a week, and she’s paid as a contractor, not an employee. Her role of “teaching artist” is intentionally flexible.
“We’re encouraged to put music kind of first, and if we have a gig or something like that, we’re welcome to sub out of Sistema and send a different teacher,” she said. “I’ve definitely taken advantage of that.”
She’s working hours equivalent to what full-time work would be, but at what she says is a pretty low wage.
“I’m not making a lot of money, man. I’m making, like, 40 to 50 thousand dollars a year, if that.”
Her third source of income is performing with local groups. For about 10 years, she’s been in a group called Juvel where she plays jazz, folk and swing music with three bandmates, but she also plays in other projects and many local acts. She says she plays gigs most weekends, but they don’t always pay a lot.
“Most bar gigs pay about $100 [per person], which is rough, because that’s what they paid about 20 years ago,” Woolger said.
Corporate gigs will pay more, about $300–$500, but those come along less frequently.
“They’re enough that, you know, one or two of those a month goes a long way.”
Many artists make their living from touring, but going on the road isn’t an easy decision. Woolger says she won’t go on tour for less than $150 per day. When she’s on tour she can’t work her other jobs.
“I’ve turned down things that seemed cool because I’m just like, I can’t afford that,” she said.
Woolger plays in a group called French Class, led by Megumi Kimata, a local beat maker. They make electronic dance pop music with jazz influences.
“I make the least money on those gigs out of all the gigs I play,” she said. “But I take them because I believe in it artistically, and I wanna be part of that vibe.”
“I think it could be something really awesome if we keep working at it.”
The Gig Triangle
Choosing work is an art of its own. In school, Parker Beesley learned a rule of thumb to choose his gigs: the gig triangle.
Based on this theory, every gig has three factors: money, hang (the people you are playing with), and music. A gig has to have two of the three things to be worth taking. Are you playing music you don’t love? You’d better be playing for a good price with people you love. If you’re ever unsure about taking something, check the triangle.
Beesley has made sure he doesn’t have to worry about the “hang” part of the triangle. He regularly plays shows with his band, The Art Department. They played a show in October at Park Alleys, a bowling alley/restaurant/bar/live music venue in South Osborne. Beesley says it’s the most fun he’s had playing in a long time.
“Those four people are my favourite musicians in the world,” he said. “I’ve seen a lot of shows, and I’ve been to a lot of gigs, and I’ve met a lot of people, and I play with a lot of people, but you know, when you build such a deep connection with certain musicians, it’s almost, like, no one else could do what Peter does on the second chorus of my solo, or when I’m comping for him on his solo, there’s just a level of trust.”
Beesley has been playing with The Art Department for about a year, and he says he feels more connected to them musically than he’s felt with anyone else in his life.
In their October gig, The Art Department didn’t play any original songs, just covers of music that Beesley loves, like “Just The Way You Are” by Billy Joel.
“I got to hear Nolan play the most amazing solo I’ve ever heard,” he said. “There’s a video of it, and I’ve cried to it many a time. Don’t tell him I said that.”

Why Work in Winnipeg?
A music “scene” is the people you hang around, the bars you frequent, the music you listen to, the festivals you go to, the venues you play.
Winnipeg’s scene is friendly and welcoming, but small and isolated. Word travels fast and reputations matter.
Woolger, who moved to Winnipeg in 2012 to go to the University of Manitoba for music, thinks the isolation of the city is part of the reason musicians here create genuine communities.
“You have to be kind to others and be helpful and friendly and, like, a cool, nice person on the scene. Because if you suck, you’ll be so lonely,” she said. “You’ll go out to the Times Changed and everyone will just be, like, fake polite to you.”
Woolger says she’s seen others go through that.
“If you don’t treat people fairly, if you are dishonest, if you, like, are generally a shitty person, people won’t be hiring you,” she said. “At least not the people you want to play with.”
She says you need to build a reputation of generally being a kind person.
The Times Change(d) High and Lonesome Club (referred to as Times Changed or the Times) is Woolger’s and many other local musicians’ regular hangout. The walls are covered with art, magazines, photos, newspaper clippings, and posters. Weathered brick fills in the gaps. Every Thursday through Sunday, local musicians and music lovers like Woolger gather there to watch or play shows.
“I’ll be there on the weekend, and sometimes it feels like a freaking family reunion,” Woolger said.
In a city and industry where networking is how you get work, venues like the Times are key.
Anthony Kost is the artistic director for Fire and Water Music Festival, an independent music festival in Lac Du Bonnet. He’s in charge of selecting the lineup. He says selecting is about 95 per cent having his ear to the ground. He follows the scene on social media and goes to shows at local venues like the Times.
“We consider that — and it has been for many, many years — an extension of our living room,” Kost said.
He’s been artistic director for five years, and he says maybe by his tenth he will have exhausted the pot of artists he hires from, but it’s working for now. He mostly hires people playing in the Winnipeg scene, which has a deep pool of talent. It can also be tough to get artists from further away to want to make the trip to Lac Du Bonnet.
“No matter what kind of tour you’re on, we’re out of the way,” he said.
Staying in Winnipeg
Winnipeg doesn’t have the biggest music market. It’s small and prioritizes art and connection. When you’re playing a gig, you’re often playing with and for friends, or at least people you know.
“Winnipeg is the smallest big city I’ve ever felt,” says Beesley. “It’s a big city in size, but it’s tiny because you spend all your time in, like, four locations.”
It’s always felt like home for Beesley.
“It’s a fun city to play in,” he says. “By the end of this degree, hopefully I’ve played a lot of gigs, done a lot of stuff and made some kind of contribution to the music community here to where I’m like, okay, I’ve done this, and I can move on to something else.”
Beesley, like many 19-year-old university students, says people ask about his future two or three times a month, and his answers vary. He wants to get a master’s degree somewhere with a bigger market, like New York City, Toronto, or Montreal. He says bigger cities have more opportunities in line with his goals: bigger shows, bigger studios, and more people.
“I would regret not going to another city and giving it a really good shot,” he said.
But Winnipeg’s size can be a strength. Woolger says in some bigger cities you have to show up to gigs with a bolstered persona — because you don’t know anyone, you’re hustling for more gigs because it’s a big market, and you’re waiting for the record executive to show up. But not Winnipeg. Here, you’re rewarded for being yourself — as long you’re kind.
“Here, the record executive is not showing up, so you can do whatever the fuck you want,” she said. “I just love when I’m part of a good music vibe that is entertaining people and saying something meaningful. Whether it’s screaming loud music, or quiet chill jazz, playing toward the music and trying to let that flow and relax into it, those are the good musical moments.”
In the gig triangle, Winnipeg always has hang and music covered — two out of three isn’t bad, right?