Graphic by Isa de Leon
Isabel Pless’s music career may have been a happy accident, but that’s not to say it wasn’t well deserved. As a senior linguistics major at Wellesley College, she has a way with words. Creating rhymes that ring and lyrics that reverberate with truth, she touches on real experiences — the ones that matter and hurt the most: familial failings, faltering love, loneliness, and growing up in a world that’s become increasingly unkind. I got the chance to sit down with her one morning and discuss everything from her discography and journey so far, to her inspirations and her trajectory for the next few years.
We started our chat by lamenting about the one thing that’s hanging over the heads of everyone our age — our schools’ plans for the coming semester. As the pandemic bleeds into its second calendar year, that familiar feeling of uncertainty for college students comes back again and again: In-person or online? On or off-campus? This feeling is something Pless captures well in her music, particularly in her single “Bechdel Test.”
“Bechdel Test” put Pless on the map, rising in popularity faster than any of her previous works. “It was really crazy, ‘cause I knew it would do OK because people online were kind of asking for it. And I remember I released it and it got 8,000 streams on the first day, which was the biggest I’d ever had, and then the next day is when it like, really blew up and all of my idols were posting about it.” Her single was even covered by TikTok famous folk-pop songwriter Lizzy McAlpine. Pless’s single garnered massive amounts of organic attention on TikTok and Instagram, and for good reason. “Bechdel Test” is Pless at her most polished and poignant yet, full of ironic lines:
“I’ve been watching too many movies / That do not pass the Bechdel Test / And that makes me feel like I am a bad feminist / But I pirate them / So that makes it better I guess.”
I’m sure we’ve all been there in our quarantine movie marathons (looking at you, Marvel franchise!) There’s something so comforting about her self-deprecation in lines like these. Pless sings in a way that feels like she’s singing only to you, baring her soul in hopes that you too feel this way. And many do, proven by her 103,000 TikTok followers and over 40,000 monthly listeners on Spotify.
I asked her about her process of writing lyrics, lauding her ability to make the complex seem so simple and vivid. “I don’t know if I think too hard while I’m actually writing, I think I’d psych myself out, but basically what I’m trying to do is take a specific feeling and make it general. It’s also stuff that’s part of the human experience that maybe no one’s expressed yet.” Pless hopes that listeners of her music get a “shared connection,” and that they’re able to listen to her words and say “I feel that too!”
She’s in a great place to connect with a generation of lonely young adults, being in the trenches herself. Like “Bechdel Test,” she created her previous EP, “Too Big for the Playground, Too Small for the Big Leagues,” alone in her bedroom “ … in between virtual classes … feeling distant from the rest of the world … it’s hard to feel like your life is moving forward but you’re just like, stuck in a room. So with each song I was trying to capture different viewpoints of the same thing, like I’m sort of an adult, but not really, and I’m sort of a kid, but not really, and I’m really lonely.” This theme echoes clearly in songs like “Politics of Lonely” and “Burn Out,” where Pless sings about the bittersweet feeling of being stuck between adolescence and adulthood.
But let’s back up. How did she get here, producing songs from her bedroom and earning the adoration of thousands of fans online? Pless has been writing music since she was 12 years old, receiving free guitar lessons from her middle school. “I have a memory of writing a song right here on my bedroom floor. I was a really big Taylor Swift fan, so I was like ‘I want to do that too!’ It’s sort of a really nice way to process my emotions and I’ve just been doing it ever since.” She began sharing snippets of her songs on TikTok in 2020, and soon after began recording full songs with just the equipment she had in her bedroom. TikTok, the wild west of the internet, has allowed a lot of new artists to strike gold and subvert the traditional structure of the music industry, which has typically excluded a lot of diverse voices. Pless recognizes this and is thankful that her career arose the way it did. “It makes me feel empowered to have so much control over my career. It’s my words you’re hearing, not anyone else’s, and that makes me feel good.”
What’s next for this budding artist? Pless, ever humble, admitted, “I think if you’d told me two years ago, ‘actually, you’re going to be releasing music,’ I wouldn’t have believed you. I have a hard time seeing an end goal. My wildest dream is that I’ll be able to support myself off my music, and that’s what the past year and a half has shown me I can do.” She’s taken a step towards that recently, performing her first live show in Boston late last year. “It was really cool. I was nervous, I think I will continue to be nervous. It was new — I used to do open mics in high school but I haven’t performed since then except live on TikTok. So it’s really cool to have the translation of my music online to playing it to actual people who have heard my stuff. It is nerve-wracking to actually see physical people there!” After graduating this spring, she plans to move to Nashville and continue working on music.
Pless sings about heavy topics with endearing honesty and wit, bringing tumultuous feelings out into the open in a way that allows her to connect effortlessly with her listeners. Her sweetness shines through in every song. Her songs, born of the last few isolating years, serve as anthems for those of us who are trying to see the genius of it all. She also has a new single out, “More to Give,” a song about perfectionism and finding peace with yourself. “I’m a perfectionist and I tend to have this idea of self-improvement that is not always super realistic and so this song is about me being like ‘I can do more, and I can be better’ when really sometimes you just have to … exist.” You can check out her new single, as well as the rest of her songs, on Spotify, and be sure to visit her Instagram and TikTok for more song clips and content.