Getting to Know Maisyn: Oat Milk Lattes, Sally Rooney, Her EP Cool Grl, and Crying on the Dance Floor

It's a perfectly sunny Saturday in LA, as I'm quickly learning is the standard around here, when I step into a cute bookstore turn cafe to meet up with artist and songwriter, Maisyn, who recently released her epically indie pop EP, Cool Grl. It's no surprise when she orders an oat milk latte to take outside to the restaurant's patio. On the Instagram story for Luna Collective that introduced me to Maisyn's music, she included oat milk lattes, "All Too Well", and Sally Rooney on the list of ingredients that might lead you to like her music. 

As we wait for our drinks and sit down, she asks about my recent move to LA and starting college at her alma mater, the Thornton School of Music. Maisyn's music is incredibly honest and confessional with a quality that makes the listener feel like her best friend. Talking with her, she carries that same instant feeling of familiarity that makes conversation flow effortlessly. 

Rewinding to the very beginning, music and storytelling have always been major components of Maisyn's life, even if the two didn't immediately blend together. As a kid, she spent her time writing short stories "really emo poetry" in marbled composition notebooks. At age nine, her grandmother gifted Maisyn her first guitar. Her grandmother played a major role in her early love of music by playing folk songs to her (and sometimes her entire Girl Scout troupe) on guitar.  

As with most artists rising the music world today, Taylor Swift played a major role in fusing Maisyn's love of writing and music together. "I just remember getting my guitar and hearing her first album and then Fearless and being like, 'Wow, this is what I want to do. She just writes songs about boys who do not have a crush on her. And that is what I will be doing as well for the rest of my life'." Considering the fact that unrequited love never goes out of style, this was a solid plan, and Maisyn has executed it beautifully.

The combination of Taylor Swift's influence and receiving the guitar clicked everything into place. "When I started playing guitar, I realized that this was also a medium I could use. I started writing songs when I was 10, and I knew pretty early on that it was linked to some sort of path I wanted to follow professionally," she says. With an eye towards building a career in music, she started performing publicly wherever she was allowed, even if it was a farmers market or a train station at seven in the morning. Through an after school music program in high school, she continued to sharpen her performance skills which forced her to push aside her shyness. Those first performances left her "hungry to do something cool" so she started calling every small coffee shop and venue in driving distance of her parent's Hudson Valley home to share her songs with an even wider audience.

For college, she headed to Los Angeles to study pop music in the center of the music industry. College was always part of the plan for Maisyn, and studying music felt like the only option to continuing learning and growing. When it came to finding a pop music focused program, though, she didn't have many options. Ultimately, LA being the industry hub led her to the Popular Music Program at Thornton where she graduated with an emphasis in songwriting. 

After leaving school, though, she fell into an existential crisis stemming from that same will to learn and keep learning that propelled her to go to college in the first place. "Did I learn enough?" she wondered at the time. "I think, after having time to process, I've just kind of landed on: I'm not done learning. I will never be done learning... At first it was really overwhelming, but now it's really exciting."

Even though Maisyn came out of college still unsure of her identity as an artist, she still values the time those four years gave her to answer many questions about what she values in her artistry and career. Her college experience also connected her to her producer, Joey Messina-Doerning, who has also worked with artists like HAIM. "We met the first day of college, which was a lucky draw," she says with a laugh. "He was in the production program at USC, and he was roommates freshman year with the one person I knew in the production program at the time. We were friendly enough to be like, 'Okay, we're gonna stick together'. The three of us became great friends." They spent college working together on various assignments for Maisyn's songwriting classes and Joey's production assignments, building up their working relationship and understanding of each other as creatives. "It's been really cool to work on this now, because we both have grown so much since then. And I feel like it's reflected in the music, which I'm very proud of."

As with most music that's been recently released, Maisyn's EP is to some degree a product of the time and space lockdown provided her to reflect. Maisyn had just moved back to LA in the winter of 2020 after spending time back home with her parents after college. All of that moving sparked a creative run for Maisyn after a long drought, and she began the early stages of creating the EP, which originally was shaping up to be more like an album.  "I was cranking out a lot of songs. And they were all kind of in a similar vein thematically. And I was like, 'Oh, sick this is an album'. It's kind of a coming of age album. Then I cut it down to an EP because albums are very hard to release independently," she says of the first evolution of the project. Because of the challenges around creating a full album, Maisyn shifted her creative lens. "Let's make it this bite sized piece of information about me... And then I can expand upon that with the next one."

While she'd gotten back in the writing groove before COVID, in the early days of the pandemic, her writing hit a pause and she, like most of us, turned towards filling her days with cooking, reading, and following the trendy quarantine activities that sprouted up online. While that time didn't actively contribute to creating a project, the space proved pivotal to her career by making room for more introspection. That time gave way to many important changes before the start of her newest chapter.

"I was thinking, alright, I have these songs that I'm going to be releasing, and I was kind of dissatisfied with what I'd released prior. Why is that?" She asked herself at the time. This period lead Maisyn to adopt her stage name and stop releasing music under her given name, Jessi Mason, like she had in the past. "I was interrogating those weird feelings I had which then lead to the name change." While she said that her stage name felt "cooler" than Jessi, she had also started craving more separation between Jessi the person and the projects she was creating.

With this shift, Maisyn moved forward with finishing the Cool Grl EP and releasing it. The tracks fall in my favorite amorphous genre of indie pop, which Maisyn describes as, "Confessional pop. It's so lyrically driven, at least to me. I think it overlaps a bit with a joke that my favorite genre is Crying on the Dance Floor". I had to take a moment to process the brilliance of labeling the Crying on the Dance Floor genre because it's absolutely my favorite kind of music as well. She identified a term I'd been passively looking for for years.

Maisyn definitely honors the confessional aspect of indie pop in her songs whether its reminiscing on the end of childhood in "Valentine Road", leaving all her emotions on the table in "Cool Grl", or sharing her insecurities on "Pool Party".

On "Pool Party", Maisyn sings about struggling with body image and how she let not feeling like society's perfect prototype ("the one recurring thought occupies me/To be a woman wanted for her body/Running through the yard in a bikini") hold her back. It's a story that's unfortunately almost universally relatable, and with society's messaging about whose bodies are worthy of swimsuits and pool parties, it can be hard to break away from. Maisyn says that writing the song helped her work out those feelings and get to a better place.

"This is something that I've struggled with my whole life, and I still do sometimes," she says. "A lot of it was simply changing my self-talk and being kinder to myself in my mind." She's been working on catching the moments those negative thoughts start drifting in and stopping them in their tracks. "There's a lot of power in embracing the fact that there's room for everybody. It's not even like space to be able to squish into. There's just enough." In an arena as competitive as music, that mindset is really the only way to get through.

Around "Pool Party", Maisyn had another profound and freeing realization. "In a weird, same vein," Maisyn continued, "I realized nothing matters. Not in a dark way, but empowering. If nothing matters then it's not like, 'Oh then I'm just gonna sit in my room'. It's like, 'Okay, no, I'm just gonna do what I want, because who cares if someone wants to judge?' It's definitely been difficult but also really exciting to feel more comfortable in my body and myself."

Looking ahead to the future, this "next one" that Maisyn referenced when she moved away from the album is shaping up to be a second, possibly sister EP. "Right now, I'm just taking it step by step," she tells me about what's next. "I'm trying to write more with other people. I'm also trying to develop my production skills right now because that was a thing that I definitely neglected in college," she says. As for possibly carrying some of the cut songs from the hypothetical album into the next project, Maisyn says that the older songs are on the table. "There are definitely songs that I'm still really into that I want to be on the next EP. I was thinking of splitting the album in half. They could be sister records." Even though she's excited by the chance to continue Cool Grl's story, there's still nothing set in stone. Work on the next project hasn't formally started yet, so there's certainly room for this second EP to change course in the process.

Considering this new era of her career that's just starting to unfold, I asked Maisyn about who she's hoping to connect with through her music. She paused for a moment to consider before saying, "It's kind of like what I put on the story for [Luna] Collective. People who like "All Too Well". Oat milk lattes. You wear Doc Martens? Yep, let's be best friends," she jokes. "I think being able to talk honestly, and through the internet in general, we learned, 'Oh, there are so many people who like the same shit as me'." It's that wonderful moment of recognition that she wants to cultivate between her listeners. 

"I think one of the most important things to me is to be seen... I hope people feel seen when they hear my music."

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