After releasing her 2019 debut what we say in private and spending months on the road, Levy found herself drained both physically and mentally. She made the difficult decision to take a step back from the momentum she’d built, embracing rest as a necessary shift for how she approached life and her art. In that time away she confronted grief and overwhelm head on, slowly reevaluating what it means to create. Her new album when I paint my masterpiece is a product of that reflection, but more than that, it’s a marker of who she’s become through the process.
Sitting down with RANGE, she explains that its title came from a visceral reaction to an early demo of Bob Dylan’s song of the same name. “I think the title (“When I Paint My Masterpiece”) captures that striving for something whole or something perfect, like a master,” she says. “You’re looking for something perfect even when you know it’s not possible. I think that is the lifelong journey of the artist.”
“It isn’t just about art,” she continues. “It’s about finding wholeness, and it’s focused on the process of ‘when,’ when I paint my masterpiece, when will that happen? Probably never.”
With sweet, stripped-down acoustic moments, bright vintage ’70s rock tones, interesting electronics and treatments, playful lyrics over ballads, and a touch of tasteful twang, when I paint my masterpiece experiments with genre and mood while holding onto a cohesive theme of self-discovery and acceptance. The record carries a subtle momentum with intention, heralding a continuous push towards something more authentic.
That sense of authenticity shaped not just the songs, but how they were recorded. Levy and her band decided to forgo a click track, a radical move in today’s digital era of precision. “Luke asked, ‘What if there’s just no click?’ I felt my stomach fall. ‘Oh my gosh we’re gonna be free falling!’” she laughs. “Who knows what will happen? But we had played the songs so much, some we had even played on tour, so we were well equipped to do it that way.
For Levy this approach was both technical and philosophical. I wanted the making of this album to say mistakes are okay, and the industry isn’t going to decide what’s good and what’s not worthy of being listened to. And why is it that perfectly robotic things are the norm? Why can’t it just be people in a room?”
That mindset of embracing imperfection, slowness and intuition, would go on to define the entire project, though it came with consequences. Levy lost her agent and manager in the process.
“At the time they were super understanding, and then I didn’t hear from them for two months until I got an email saying ‘It seems like we’re going different ways, you’re wanting to take a step back from music. The only thing I know how to do for a project to grow is to have the artist on the road,’ and it just really didn’t feel good to me,” she says. “I totally understand their viewpoint too… You’re kind of anti-industry.”
Levy then returned to school, started teaching, and created a songwriting challenge and workshop with one rule: submit a song by 11:59 PM.
“I had writer’s block for like five years. I couldn’t write anything. I hated everything I was writing, and then in one month I had 10 songs. At the end of this year I will have 40 songs,” she says.
“All creative works are just a series of small decisions. If you know you have the clock ticking, then you’re going to make a decision, whether or not you think it’s the best decision. It does make for different kinds of songs. Some are bad, some are good, but it is just a numbers game.”
As she rebuilt her practice, Levy also reimagined how she and her band would tour.“Chris, who plays guitar, was like, ‘I do not want to do a drive for a show that’s gonna be over five hours.’ So that was rule number one,” she says. That one rule reshaped their entire approach as a band. Levy adds, “If you’re not waking up at six after going to bed at two, then you can be well-rested and you can feel good and have a nice time. So we’re gonna try this out and see how it goes… I’m curious, can it feel good to me?”
Levy knows she’s not the only artist resisting the grind. Many musicians like her have spoken about grappling with connecting with an audience without relying on platforms like TikTok or pumping out ‘content’ for social media. Levy mentions that, for her, time spent on promotion often comes at the expense of actual creative work – not to mention the exhausting toll it takes on her. Instead, letting go of these industry expectations has brought her a sense of relief.
“At the end of the day, if you’re not willing to do certain things that the industry is now expecting of you, then you need to just have this sense of trust of, okay well, I guess things will pay off eventually if I just focus on what’s good for me,” she says. “And I think that means that maybe I won’t find listeners in this lifetime. It still doesn’t change my desire to work on music and to paint and to have creative projects. It’s a weight off my shoulders.”
As she looks ahead to life beyond the record, Levy is also thinking about how to help others find their way to creativity, something that she calls “the most natural thing anyone can do in our hypercapitalistic environment,” one that doesn’t give people the space to prioritize projects like the ones she wants to. As she continues to make space for creativity, she’s also turning toward even more personal, often unspoken experiences.
“A year ago, I had a termination for medical reasons, which is just something that isn’t talked about in art and in the media,” she shares. “It’s very complicated. There are all of these intersections for TFMR. That’s what I would like to work on processing next. There’s a lot going on in the world that I don’t feel smart enough to be able to put to song. So I always just stuck to the personal because that felt most true and authentic, and a way to escape the realities of what’s happening worldwide.”
So what does Levy want people to feel when they hear the record? “I don’t know what my goal is for the listener,” she says. “I do hope people come away feeling like there’s a bit of mystery or magic, no answers to specific questions.”
That open-ended spirit marks a new chapter for Levy, one that turns inward with even more intention, both in sound and in process. She may never paint her masterpiece, but reaching for it is what it’s all about.
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