JESSIA and I are sat in the back of the Drake Cafe after hours. It’s not even 6 pm but you wouldn’t be able to tell by looking out the window: the night is already so dark one would mistake it for past midnight. Blame daylight savings. Outside, fans had been lined up since the early afternoon, awaiting JESSIA’s arrival (I had walked past them several times already, each time the line was longer as the day got colder). It’s the first time we’ve met, but her presence is as comforting as it is captivating, and we start chatting as if we were old friends catching up.

Halfway through the interview, we’re interrupted by a Drake Hotel employee questioning us, confused as to why we’re sat in the now-closed cafe. Despite our reasoning and futile attempts at explanation, he kicked us out, and up we were, shooting each other curious glances and sheepish grins.

We didn’t make it far—about halfway down the stairs to the Underground, to be exact—before we were approached by two young girls, both of whom were instantly starstruck to be in JESSIA’s presence. As she spoke to them, with a gleaming smile and words charged with an earnest excitement so genuine it couldn't possibly be feigned, I found myself wondering: does that feeling ever lose its magic? Standing there, a beacon of light to strangers who don’t know you but still sing your songs back to you, their voices echoing your own under the stage lights. It couldn’t possibly get old, though I wonder how long it takes for someone to adapt to that way of living. As she hugged one of the girls (who took the quick interaction to explain that she would be taking photos of the gig for the night and thanking her for the opportunity), another member of the Drake came rushing down to grab us, apologizing profusely for the mix-up and escorting us back into the cafe to finish the interview.

After giggling about the whole affair, we felt trauma bonded and became instant friends.

SIERRA MADISON: This is your first headline tour, which is super exciting. How has that experience been and what’s been one highlight?

JESSIA: It's been so fun. It's different from being an opener, because as an opener you just play your songs and get off the stage, whereas I love yapping. I love meeting my fans, I love being able to hear their stories: how their day was, you know, I'm here for them and they're here for me and it's this cohesive thing. So being able to take the time [during the show] and be like, “Hey, what's going on?” or, “We're stopping the show. We're gonna work out some of this drama girly. Let's go. Let's get it.” That's a really, really big highlight that I didn't realize I missed in my opening sets, just being able to connect with the fans more.

SM: In 2023, you decided to start releasing your music independently. How has that journey been for you and what role do you think social media has played in allowing you to make that decision?

J: Oh my goodness, I mean as crazy as it sounds, you definitely do feel like your family is gone. I'd built such a beautiful family with that label, but it was definitely time to go. I think it was a really, really big transitional period, but being able to show up [on social media] the next day and realize that you've still got the same people commenting, the same people following, like, they've got you. And so not having social media, I think that I would spiral. Social media is such a double-edged sword, but it is incredible in the way that I'm able to just see my fans on a daily basis and be able to talk to them and have that connection. And now on the other side of it, being healed, it's so sick. I'm my own boss, and I'm able to just be like, “Let's release a song tomorrow, guys.” And it's just this small little team running this whole thing. So I'm very, very grateful.

SM: That's awesome. Do you think the decision to go independent has allowed you to express yourself more freely? Do you feel like you have a lot more creative freedom now?

J: I feel like it's just a lot more me. Because getting signed to one of the biggest labels in the world, I was just like, “They know best. They know me better than I know myself.”

SM: It’s like a toxic boyfriend.

J: Oh my god, it's literally like being in a toxic relationship, yeah. But there were a lot of really, really beautiful relationships that I did make in that. But there were also a lot of people who were –

—- INTERMISSION AS WE GET KICKED OUT —-

SM: We got kicked out of the Drake Cafe…but we’re back.

J: He was like, “I didn't know who you were”, I was like, “That's fine. My music isn’t your demographic.”

SM: He’s like, “I have no idea who you are. Junos?… I don’t know her…” Well there we go, we broke the ice, we’re besties now, I feel like we’ve trauma bonded.

J: I was like, “Not a man kicking me out when I'm trying to do my job.”

At this point, we were giggling like schoolgirls.

SM: As an independent Canadian artist, have you found it difficult to make space for yourself in the music industry? I think a lot of times it's very dominated by American or British artists—I feel like there's not a lot of space made for Canadian artists. How are you paving your way?

J: Canada is so supportive of their artists. I mean, coming back home is so refreshing. I'm very, very thankful that Canada is so supportive of their artists. I think that we're all just trying to make a little splash, but I find that social media definitely helps because you are able to reach whoever. And the amount of people that are like, “I popped off in Africa” or “I popped off in Asia” and you're like, “This is sick.” So I find that you're able to find your audience wherever. Sometimes you feel like a small fish, but on nights like this, I feel like I'm a big fish.

SM: You got kicked out of the venue. That's big fish material.

J: Woo! Exactly.

SM: This poor guy is going to hunt down this interview. He's like, did I get a shoutout? (You did king <3)

SM: What would you say is one of the main sources you draw inspiration from? Or if you have several, what are they?

J: Again, I love yapping. I'm such a talker. So going for walks with some of my best friends, or I love podcasts and love just listening to people talk about their lives and navigating this weird little thing that we're doing with ourselves. It's an excellent question, I do find I get inspired by going for walks and just being around people. Which makes writing sessions and being in studios really interesting for whoever's working with me ‘cause I just need to go outside and need to be around the people that I'm writing for and picking up different energies and even making up stories. I've written so many love songs about a dude that I just saw drinking coffee or something. And I'm like, “Yeah, you're my husband.”You’re my soulmate. You don't know, but we're in love. And congratulations, you have the most beautiful love song written about you.” (sooooooo real)

But yeah, I get inspired by literally just walking around. Just by life. I feel like my music is very conversational, like journaling. Kind of like opening the diary.

SM: You released your EP Okay With Every Part earlier this year, and now that it's been out for a few months, what’s it like having it in the world and having other people listen to it, and hearing what feelings it stirs up in people?

J: I feel like it's always very vulnerable releasing something of that magnitude. It feels so good—I love it when people say, for instance, “Oh my goodness I love ‘Happy Without You’,” which isn't even the focus track or a single or anything. I love hearing that people have listened to the whole thing and didn't just listen to the singles. There’s a period after I release the songs where I'm like, “I don't want to hear these songs for a little bit.” And then now, I'm so stoked about them, and I want to go back and start pushing them again. That's the other thing about this time in music—songs don't die. Songs can pop off from, like, 20 years ago.

And so I feel like going back and listening to them is like saying “Hi friend. How's it going?” But yeah, it's been lovely. The fans have been screaming every single lyric back to me. It's crazy. It's so wild. It's so surreal. There’s this feeling of, “Who are you? What is going on?” There's also always this weird sensation of someone else taking your work and having their own personal stakes in it and having it invoke feelings in their life. Sometimes I'm like, “This was not that good of a piece,” or “I didn't like how this turned out,” and yet this other person is like, “This is the best thing you've ever written.” It’s the most amazing thing ever. And now, being independent and knowing that it's everything that you've worked so hard for, it's so cool when I've released a song that I'm really proud of and like being like, “This is sick,” and everyone's like, “Yeah, we agree,” and we’re all in it together.

SM: What are three things you can't leave the house without?

J: Lip balm. Lip balm’s a big one. I'm trying to leave my house without my phone, but I’m like, “Dude, we're not gonna do it.” And, I don't know, probably a hoodie. I'm just always so scared of being cold because I turn into a bitch when I'm cold. So I'm always like, “I'm gonna take layers and if I have to carry this layer, then that's on me, but I would much rather be hot.”

SM: My last question is what's your favourite part of Toronto?

J: Oh my goodness, favourite part of Toronto…I love the food and all of the different cultures. It's absolutely incredible how you're able to just go into these little holes in the wall and you're like, “This is like the best meal I've ever had in my life.” I also really, really love going to the islands as a nice little break. But I stay in this area a lot whenever I'm here. So I always walk to Trinity Bellwoods. It's so cute. Yesterday, I was literally on vocal rest and I just sat and watched Squirrels. And I was like, “Am I 80? Or am I living my best life?”

SM: Yeah, that's what I do every Sunday too.

J: They're so great and their little fluffy tails are so cute. Favourite thing about Toronto might be the squirrels. The squirrels are really cool.