Want to quit your day job to DJ full-time? Here's what it takes

In Making a Living, we talk to artists and creatives about all things money — how they make it, how to support an artistic practice when you still have a day job, and how to handle things like taxes and slow periods when you're doing it full-time.

If you are into electronic music, or hip-hop, and particularly if you're into the spaces where those genres start to overlap, then you probably know Jayemkayem. Since she began DJing in 2014, the U.K.-born, Calgary-raised, Toronto-based DJ has moved crowds on multiple continents, at venues ranging from sweaty basement bars to venues with a capacity of thousands, as well as working with brands like Nike, Tiffany and Co., and Red Bull.  

She also does what she calls a lot of "miscellaneous freelance creative work" for other artists and musicians, including social and digital content and public relations, a skillset she developed in her previous life working in marketing and corporate communications. On top of that, she's the co-founder of ISO Radio —a not-for-profit internet radio station in Toronto that gives the city's club DJs an opportunity to try new things and flex their skills in front of new audiences — and the independent record label Bare Selection.

We talked to her about being one half of a musical couple, the difficulties of touring in Canada, when it's time to walk away from your 9-to-5, and how going back to a 9-to-5 isn't always the worst thing. More than anything, she says that in order to make a living as a DJ, or any type of creative worker, you have to know your value and be willing to ask for it.

Who are you and what do you do?

My name is Josephine Cruz. Some people know me as Jayemkayem, which is the alias that I perform under. I'm a DJ and a performer, but I also do a lot of freelance creative work, mostly in the music space: content creation and production. I've done PR… I also come from a media background, so I've done [freelance] writing and I still do a little bit of that. I was just on tour with, I don't think you should put their name, but [a stadium act]. I was just working on that tour, doing all their digital content.

How did you start DJing?

I was always really into nightlife. I've always been a party girl. My ex-partner in Calgary was a DJ and we used to do a lot of stuff together. I was promoting and he was DJing. So I learned a lot about DJ culture and how to actually [DJ] just by being around. When we split up, I missed being around that energy. He gave me a few pieces of old equipment when we split up — we still get along really well — and then I bought some stuff. I was just kind of a bedroom DJ for a little while, making mixes and putting them up on Soundcloud. Then it just kind of snowballed really organically. Someone heard a mix that I had made and was like, "Hey, I'm doing an event, we would love to have you play it at it." And then it kind of took off from there. 

What represents the biggest chunk of your income? The DJing or the content and PR stuff?

Definitely DJ stuff — mostly corporate work — like when I DJ for brands. If you see me DJing at a bar, I'm making like a couple hundred dollars. That's not the money maker. That's just for fun. When I first moved to Toronto and started getting [corporate and brand] opportunities, I didn't really know how to charge for that kind of stuff. I was like, "Oh yeah, it'll be X amount per hour." But now, after a few years, I've shifted my mindset away from that and I started looking at it on a case by case basis: who is this brand or company that I'm DJing for? The time definitely factors into it, but also what kind of event is it? How many people are there? Is it a large event that they're selling tickets for? 

If I'm deejaying this huge event that's got hundreds of thousands of dollars of budget, it's going to be a different price than a small, intimate dinner. I think that was a game changer for me: understanding that I'm not just a DJ, I'm a brand on top of that. If they want to work with Jayemkayem the brand, there's a certain cost associated with that, too. I'm bringing years of expertise. I'm bringing the hundreds of events that I've done for global brands. I'm bringing all that to the table. 

You were kind of DJ by night and then had a pretty good corporate job during the day for a long time, right

When I was living in Calgary, I had a job in marketing at Shaw, the telecommunications company, and then was DJing on the side. Then I moved to Toronto, and I was doing various freelance work. I had a contract at a media startup, and I was still DJing on the side and then eventually [DJing] just kind of took over my time and energy to the point where I could be full-time. So I DJed full-time and did freelance projects on the side to a smaller degree, all the way up until March 2020.

Right, how did you handle the pandemic? The end of live events must have been hard for you.

I think I did pretty well, to be honest, during the first year of the pandemic. I was doing a lot of virtual events. I was streaming on Twitch and just doing anything I could basically. But in the second year of the pandemic, in 2021, I was just really burned out. I was tired. And I was just like "I feel like I'm fighting for my survival all the time, I think I need a break. I need to take my foot off the gas." 

I had been doing a contract at the time with this content agency, and it just kind of happened that someone was leaving and there was a full-time position opening, and they were like "Do you want to take this?" So I ended up with a 9-to-5 working from home. I was over there for about eight months. Then I moved into another company, that was really corporate, and I was in a corporate communications role. 

Even as [recently] as January of this year, everything was closed down in Toronto, I was still hesitant like "Is [DJing] going to come back?" I was still playing it really safe. So I hung onto that job until the summer, basically, and I was like, "OK, now things are hectic again. I actually can't balance all of it. Something's got to give" — but it's not going to be my creative work, my passion and love, right? So I ended up losing that job. But a lot of people might have looked at me online and not known that I had a 9-to-5 job. I think that it can be really good to have that stability. I know for me, it just kind of allowed me to take my foot off the gas, and just be like, "OK, I can breathe and pay my bills and pay down some debt and do all that stuff."

What made you feel like you could go for it and start DJing full-time, both the first time and the second time?

The first time, when I first moved to Toronto, I still wasn't very confident in myself. I was still kind of new at [DJing.] That time it was more about when I physically couldn't anymore: "I literally can't [keep doing] all these things I've been doing. I need to make a choice." 

This second time, I made a checklist. Have I accomplished all these things that I was trying to achieve when I went back to full-time work? Have I saved a little bit of money? I'm pretty on top of my finances. I watch them very closely and I think that helps sometimes. It's a bit hard to know when the time to make the leap is, so [it's good] if you can attach a very quantifiable milestone to it, like "Hey, I have this number in mind that I want to earn every month for my [creative] stuff. Have I been able to earn that, or an average of that, over the last few months?" And if I have, maybe that's the time to do it. 

So, often when you have a couple where one person is pursuing a creative line of work, the other partner has a more stable gig, but your partner is Freeza Chin, who is also a DJ and producer. What are the pluses and minuses there?

I think there's more pluses than minuses. We always say how lucky we are to have someone to go through life with, who understands everything that [each other] is going through and where we're always on the same page, [and] can talk really openly about challenges. One key thing is you have to be really open about your financial situation. We keep our money pretty separate, but we're very open with each other about what's going on. Like, "Hey, this is kind of like a slower month" or whatever. It's important to talk about those things. But it's definitely a challenge, there's no stability there. 

I think that you kind of have to be even more rock solid in your relationship when you're in a situation like that. I'm really thankful to have someone who understands everything and we can share a lot of work, too, which is awesome. If I get hit up for an event I can't do, he's the first person that I can pass it to.

This summer, you were Cadence Weapon's tour DJ. Recently, he wrote a piece in Toronto Life about the economics of being a touring musician. Do you have anything to add on that front?

First of all, Rollie is absolutely a gem of a human and an artist. We had the best summer ever doing shows together all over Canada. He's just so great and so smart. I learn so much from him all the time. I think that it's scary times out there. Every day on social media, I see shows being cancelled or postponed and, and although I obviously don't do touring on the level that [bands and rappers] do and have those same kinds of expenses, I think a lot of the things that he spoke about and broke down in that piece are super relevant to all creatives. 

Ultimately, everything is just more expensive, and the amount people earn hasn't really gone up that much. I think there's something pretty serious discussed there and I honestly don't know what the answer is. I wish I did. The big, big artists out there in the world, like this tour that I just worked on, I'm sure they're feeling the pinch, too, but they can at least put like 50,000 people in a stadium.

It's the [mid-level artists] that are really going to be hurting, you know? And I think in Canada we also have this unique challenge, in that we don't have a lot of major music markets in close proximity. In the States, New York, Boston, Philly, Washington, D.C. — that little strip there — there are some pretty major music markets that, if you're a smaller musician who wants to tour between them, you could probably make it work. We don't have anything like that here.

So, how much are you making right now, ballpark? 

I pulled up my document with the actual numbers, in case you asked. This summer, starting in May, I made between $8,000 and $12,000 a month [before expenses.] But its kind of tough because another thing about my work is that a lot of the money you make goes back into your work. 

So what are some of those expenses?

You know, you have to consistently invest in music and equipment. You're paying a lot out to subcontractors. I might send an invoice for $5,000 for a gig, but then I'm paying out the guy who does the sound, or other DJs. Transportation is a big one. I own a car, but I'll take an Uber if I'm doing an event down in like the Financial District. Then there'll probably be surge prices, and now it's like $150 round trip. There's subscriptions to record pools and music services, and the DJ software now is all subscription based, too. So that's at least $300 or $400 a month. This year I bought a new DJ controller, that was like $3,000. Obviously you're not going to do that all the time, but when you do, it's a pretty hefty expense. 

Do you get any non-cash perks?

That's what's nice about working with different brands. A lot of stuff I might spend money on, I might get for free. I get shoes for free. I get clothes for free. I get these Beats earbuds that I'm wearing for free. 

Let's talk about taxes. Everyone's favourite subject. 

[Taxes] used to be the most stressful, terrible time for me. I always hated it. But about three years ago, I got a really good tax accountant, that was a referral from someone else who worked in my industry. He knows what he's doing, he knows all the ins and outs. So that's been life changing, and now I don't stress as much anymore because he's just great and knows how to break it all down and put me at ease. 

He was able to help me a lot by going through two previous years and seeing where things were maybe a bit messed up, helping me redo those taxes and getting a little bit of money back. That's helpful. I'm really diligent about saving all my receipts. I know there's a lot of programs you can use now where you take a picture of your receipt and it does it automatically, but I actually prefer to go through it manually and do everything right because I just feel like it helps me to understand where all this money is going. 

You have the big accordion folder?

I have the accordion folder. Exactly. I separate everything by the month and then at the end of the year, I go through and I literally enter everything into a spreadsheet that has formulas that separate the different categories. And then I give that to my accountant. 

OK, any advice to DJs or any other creatives starting out?

I try to tell younger DJs and musicians, take the time to understand the business of what you do, and understand that you are a business. Unfortunately, your taxes and all that stuff sucks, but it's not just going to go away. You kind of have to face up to it — face your fears. Definitely take an active interest in the money side of what you do. That's my word of advice.

This interview has been edited for length and clarity.