On letting your mind wander and your creativity flow

You and Winston [Case, husband and music video director] have your own home now rather than living with your in-laws. Can you talk about how that’s benefited your creative process?

I make a lot of excuses for why I can’t be creative or don’t want to sit down and write something, and I used not having my own space as an excuse for a long time. Once I get what I want, I’m like, “This isn’t working either.”

I’m feeling a lot happier now than I have in a long time, and maybe that’s because I have my own space and it’s been stable for a while, and I’m starting to feel more in touch with my creativity. But I have this dissociative thing where I made an album that’s coming out, but I don’t really remember making it.

Can you talk more about getting what you want and it still not working?

It’s easy to chalk up unhappiness to not getting what you want, and then the real unhappiness sets in when you get what you want and you’re still unhappy. I think lots of people can relate to that.

To what extent do the collaborators you work with help you address that?

So much. The enthusiasm that other people have definitely pushes me forward. The enthusiasm that Winston has, he’s always been a huge fan of music, a much bigger fan of live music and concerts. I like going to concerts, but he fucking loves live music. When he was a kid, he would just show up at venues in San Francisco and hope they would let him in, even though he was underage. His enthusiasm for music has definitely rubbed off on me, and he’s a huge collaborator. The producers I worked with on [Love Hallucination] definitely inspired me to keep going more than I can myself.

From what I recall from when we last talked, Winston is more of a video collaborator, not a music and production collaborator. Is that still true?

Yeah, but he’s constantly finding music to listen to. We listen to that in the car or at home, and so in that way, he has been a musical collaborator for me, because I get most of my inspiration just from finding other artists that I like, and he’s helped with that a lot.

It sounds like, just by spending time with your partner, you’re getting inspiration through basically osmosis.

Definitely, yeah. He has an infectious joy for music. My experience when I was a kid was, my dad was very strict and forceful in his idea that I was going to play piano, I was going to be really good at music. There wasn’t a lot of room for joy. During my first connections with music my dad was kind of a tyrant, so it helps to have that osmosis effect with Winston.

What’s your relationship like with piano these days?

It’s huge. I don’t have an acoustic piano anymore, but I learn songs all the time. I play them on my keyboards and basically do the same thing I used to do when I was in school for jazz or when I was taking piano lessons, and then apply it to songwriting, so I use it all the time.

On your first three albums, you were mainly co-producing with Jeremy Greenspan [of Junior Boys]. On Love Hallucination, there’s a Jacques Greene co-production in the mix. Why did this feel like the time to start bringing in new collaborators?

I had lots of ideas and I was writing songs, but it felt difficult to finish them. It was right as people were starting to emerge [from the early pandemic] and get together again. Having people over was really fun. It was more fun than I’d had making music in a long time. Jacques came over to my place, and we worked on stuff together, and that was really exciting. It’s just more fun that way.

I really do think of music as a team sport, and sometimes, it’s easy to fall back on this myth of the mad scientist or whatever. I think I’ve also put the idea on a pedestal that I have to do things alone in order for them to be great, or take on so much by myself, and it’s not as much fun to do it that way all the time.

It’s tough, because I’ve been in a lot of situations when I was younger where I felt like asking for help in music, or being in a position where I was vulnerable, just felt really bad. It’s like, well, how do I get away from that? So I learned to do everything by myself. That’s been really empowering, and it’s helped me in so many ways.

It’s kind of walking the line. It’s like having both those feelings at the same time where you want to do all these things on your own and you want to know how to do it, but you also want to collaborate. In the past, I’ve been afraid that collaborating falls into reliance, and reliance falls into vulnerability, and then I’m in a position I don’t want to be in. I’m walking that line all the time.

What are some of the challenges that come with collaboration for you?

I go into things knowing that I have people’s best interests at heart, and you just have to hope they’re going to reciprocate. But the fear that they won’t or that they’re going to do something without your consent, or release something early—there’s paranoid thoughts. That’s a challenge for me, but I also don’t want to live like that at all. It’s just trust, really.

When you were talking about when Jacques Greene came to record with you, it made me think about how he flew to LA to spend time with you, whereas in the past when you were both based in Canada, I’m sure meeting in person would’ve been much easier back then. How has geographic distance affected the way you collaborate?

Being away from my family, and from basically everybody I was close to for the majority of my life, has helped me be my own person, as corny as that might sound. I took for granted that there was a lot more of me as an artist to explore. I just needed to get away from everything that was familiar.

The distance has helped a lot. It’s given me a lot of confidence. I wrote a lot of songs for other people. The last two or three years, I got much more into doing that, and that’s helped me build a lot of confidence as an artist and songwriter.

Can you talk more about how writing for other people has shaped your confidence?

I’ll get an email from a manager and it’s like, “Would you do some production or writing for such and such artist?” I’ll start listening to their music. I’ll look through all their social stuff. I’ll get an idea of, who are these people from a superficial standpoint, and then, it’s really fun to get into, what do I think a song by this person would sound like, or what would be a fun direction to take this artist’s music into?

A lot of that work got rejected. One song that ended up on Love Hallucination [“Marathon”] was a rejection song by another artist that I had written in their voice, with them in mind. I liked it a lot, and I found that it worked for me, which was super fun. I took chances and did things I wouldn’t have normally done for myself.

When I heard the sax solo on “Marathon,” I was, like “Wait. In a Jessy Lanza song?” Don’t get me wrong, it works, but I was surprised.

I was also surprised that it worked. That was a shocker for me, too. But yeah, it does work. I really like it. It’s one of my favorite songs on the record.

When you were talking about the benefits of geographic distance for your collaboration, I wrongly assumed you would say something about how different it is not to be in the same room with your collaborators since you don’t live in the same country or province anymore. To what extent do you feel that, or that it’s harder or easier to communicate and collaborate through email?

You get a lot more done if you’re in the same room, but it depends. People are so different. The song I just did with Tensnake called “Keep It Secret” was super efficient. That was the most efficient email song I’ve ever done. We’ve never met in person. I don’t know what his voice sounds like. I’ve never spoken to him on the phone. But we did that song really quickly and then it’s just a case-by-case thing. Sometimes, the distance matters, and sometimes, it doesn’t, but I like the in-person experience as an anchor. It feels better to be with somebody for sure. I can’t deny that.

How do you know when a song is done? Or is it more like, it’s never really done, but you just get it as close as you can?

It really comes down to instincts. If I feel good about it and the people that I trust that are listening to it feel good about it, then it’s good to go. But it’s definitely just a feeling you get in your gut that it’s done, and it’s time to either release it or can it and move on.

How do any notions of failure or success play into your journey of building out your demos into fully produced songs? Are there any ways in which you find success in failure?

I’m thinking about failure all the time, but then, I just have to reflect on my much younger self having dreams and ambitions and thoughts of what success would be to me then. I can remember reading the little weekly in Hamilton from Toronto. We would have show listings, and I remember as a teenager thinking, if I could just play a show in Toronto, that would be it for me.

It comes back to getting what you want and then maybe not being as happy with that as you think. You have to put it all in perspective and take the wins as they come. I think about failure all the time and have to check myself and remember that I’m so lucky to do the things I do and be able to play shows for people and travel. I’m in a pretty good spot, so I try not to dwell on the idea of failure too much.

I think it’s really easy to get lost in, “more, I need more, I want more.” Whatever the “more” is—more fans, or more money, or more acclaim—it’s just a losing game, really. That’s another line to walk, of being ambitious but also regularly checking yourself.

To what extent do you feel like these would be considerations if you were making music only to make music, not with fans and money in the equation?

It would be a lot different, but now, more than ever, it seems hard to separate them, to pull them apart. The making music and the numbers, it just seems like, as an independent artist, all these things are so. if you’re not talking about them, it seems like you are talking about them at the same time. It’s hard to ignore.

How have you managed to make a living from your creativity?

Honestly, Red Bull. It sucks that they don’t have their music division anymore, because they definitely kept me going for a long time. It’s just big brands, big companies sponsoring big festivals and having the ability to give you one big paycheck that will help float a whole tour. There’s not a lot of money in just making music, so writing for other people, understanding that residuals are important, that’s helped. But it’s tough. I think about that all the time, and if I think about it too much, then that gets in the way of being creative. I try not to dwell on it too much and just take one project at a time, but it’s tricky to balance.

You’re saying it takes a lot of work to be a career musician. Is there ever a day off, or a day away from creativity, in your creative process? What does that look like?

I have a lot of trouble taking days off, and it’s not to say that I don’t do nothing for a lot of days of the year. I’m not working all the time, but I’m always thinking about, what are the possibilities, what could I be doing? It seems like that applies to everything and everybody. Music might be unique in that you used to be able to make money and now you don’t, but it seems like…everybody’s struggling with this question right now.

What exactly does your day-to-day look like? Can you walk me through your creative process?

I have tons of lists that I make of songs that I like, songs that I want to learn, songs that I want to sample. But honestly, I don’t make music for stretches of weeks at a time. And then, it’ll all come very fast, and it’s hard for me to remember that all those lists and all of the thinking, that’s work, too. A lot of my creative process is thinking and then forcing myself to act, even if that’s writing something down or recording something small. That’s all part of the process.

I think a lot about being creative, but I can be quite cautious about it, which is ridiculous and something I’m trying to be more flexible about. Working with other people helps break me out of the habit of thinking too much about what I’m going to do or what I want to do, rather than just doing it.

That’s a really nice note to wind down on, but if there’s anything you still want to say about the nature of creativity, or anything more you want to say to any of the questions I asked but didn’t get to say when I originally asked them, please go ahead.

I think we’ve all been forced into this idea of, our time is so valuable, and it is valuable, but thinking of it that way is the antithesis to creativity, to just letting your mind wander, letting things happen, letting things come out, just letting your creativity flow. I’m fighting to let myself just go, because everything seems so accounted for. I think that sounded more negative than I wanted it to, but finding time to just really not think about much is something I’m always grappling with in my creative process.