This photo was taken in my high school, Westdale, in Hamilton, Ontario. I immediately think of concert band. I was very into playing music; at that time I would’ve been working on getting my Grade 10 piano in the Royal Conservatory exams, playing clarinet, singing in jazz bands. When I see the lockers I think of my clarinet case being in there.

I tried very hard to be a good student. It was a hard time because my dad passed away that year – it’s weird to look at that photo and see that I’m smiling and just trying to be a 16-year-old but I was emotionally a bit fucked up. It was the first time something so sudden happened to me, drastically changing my life – I hadn’t really dealt with anything like that before. But my mom and my sisters were there, and they’re still around.

Hamilton has changed quite a lot recently. It’s like a rust belt town; a Pittsburgh, Cleveland or Detroit. It was a big steel town and then that evaporated and it got pretty unpleasant. Not a lot to do, downtown hadn’t been rejuvenated yet… I think of it as a chip-on-its-shoulder city. Even now, people always have something negative to say about Hamilton. People call it the armpit of Ontario.

I do go back there a lot. When I was living in New York I drove back all the time, like once a month. I was working on a record with my friend Jeremy Greenspan who still lives there, so before Covid I was there pretty often. I’m super close with my family too. It’s quite different now: there’s an art scene that’s more visible, downtown has rejuvenated, people are opening stores and spending time in the city centre. The football team is called the Tiger-Cats and people just go nuts for that, which I don’t understand…

Music was a big thing for me since I was very young. Both my parents were musicians and played in bands. It was a big part of my identity, and that was how I connected with people socially. I was into movies too – I used to think that watching Requiem For A Dream made you interesting – and I was going to parties, but I was always very focused on music. I’m the person who sings in assembly; I was into music; I was going to do music at university. My parents gave me the confidence to do it but I got made fun of a lot at school, as happens if you stand up in front of your peers in high school.

I was mainly playing jazz standards. I did write some songs as well, but they were really terrible. I didn’t know what to write about, I was just doing approximations of pop songs – maybe that’s not so different to what I’m doing now. At that time, I was much more focused on the academic pursuit. I had to get my classical Grade 10 so I could get my teaching certificate and apply to university to go and learn jazz piano performance, which I eventually did.

I loved rap and R&B, and people like Jill Scott and Erykah Badu. I hadn’t seen people who incorporated jazz music in a way that I really liked, and those bands were my obsession at this point. I was pretty stoked to go see Talib Kweli in Toronto. I took the bus to go see him through a snowstorm. Bands would never come to Hamilton. You’d have to go to Toronto to really engage with the music I loved then.

My dad had a studio in the house, and although I wasn’t able to use the console I could play the Fender Rhodes that was in there, and a Yamaha DX7. It’s funny, so much of my relationship with my dad was around music – he was a teacher but he also had a PA rental business. He would go and install soundsystems in clubs, and I would go with him to these auctions and buy all the speaker components, the subs, the cones, help him paint them, go and lay the cables and stuff. He had all these great drum machines and synthesisers, and when he passed away I inherited them.

But it wasn’t until I started working with Jeremy that he started showing me how to put the pieces together. It was a bit of a hump for me to get over – it wasn’t until a good 10 years after that photo was taken that I really learned how to use all this equipment my dad had left.

What would I tell the girl in the picture? I would say you should break up with the guy that you’re with in the photo [cropped out], and don’t listen to any of the bullshit that people in your grade are saying. Just focus on the stuff you care about.

As told to Luke Cartledge