Now that we’re 11 episodes into the OK Show, I realized that I’ve started to weave a bit of a tangled web between some of my guests. You may remember that season 1 wrapped up with Manchita of GRRRL PRTY, and season 2 kicked off with one of Manchita’s collaborators in GRRRL PRTY, Lizzo. Well we’re going to keep that family tree branching outward today as we explore the backstory of another artist who has crossed paths with Lizzo, Claire de Lune. Claire broke out in Minneapolis as a singer in the hip-hop trio the Chalice before leaving the group to launch her own project, tiny deaths.

I have a tremendous respect for Claire — and not only for her artistry and her gorgeous voice, which has blossomed and matured significantly over the past few years, but for her ability to very clearly and movingly convey her thoughts about feminism, anxiety, and the inner-workings of the music industry.

After a few late-night exchanges on Twitter, I quickly realized that Claire and I have a lot in common. We both deal with anxiety disorders that try to knock us off our game, we both deeply identify with imposter syndrome — a.k.a. I’m not actually talented and the successes I’ve had in my life must have all been accidents! — and we both want the music scene in the Twin Cities to be more inclusive for women.

When Claire’s new project, tiny deaths, placed on City Pages Picked to Click poll in 2014, she was literally the only woman to be featured in that music-heavy issue. This year, she wrote a compelling essay about the misogyny that still runs rampant in the music world, and some of the slights both large and small that she’s experienced while navigating music venues as a woman.

I knew Claire and I would have a lot to talk about, and indeed we did. The following 30 minutes are only a small part of our full conversation.

A transcript of the conversation is below, edited for length and clarity. Find the full conversation in the audio above, download it on iTunes, or find the O.K. Show podcast through Feedburner.

Andrea Swensson: I know you have new music coming out soon. What have you been working on lately?

Claire de Lune: My life has been pretty consumed with this next EP that tiny deaths is putting out in the spring. It was a bunch more songs, then we kind of whittled it down to four, and maybe something will come of the other songs eventually. So that's been the last year or so of my life. During that time, I was also — which I think kind of informed this project in a weird way — working with Ryan Young from Trampled by Turtles, where I was playing acoustic guitar and he was playing fiddle. Trampled's been so busy, and I really wanted to get another tiny deaths record out anyway, so I've been mostly focused on that, but I think the songwriting muscles that I was flexing with Ryan really added a lot to this tiny deaths record.

When it's just you and an acoustic guitar, and there's no vocal effects and there's no big, boomy bass, it really forces you to focus on the song. And I think having that exercise kind of made me step my game up, writing-wise, on this tiny deaths record. I mean, I'm the most proud of these songs than I ever have been ever of anything. And I felt like that with the last tiny deaths record, but now I feel that way — I've never been more anxious and excited and impatient for people to hear something I've made.

I'm really interested in the progression of your voice. I feel like in the last year, especially when I watch you live, you've just kind of hit a new level of performing. Your voice sounds so strong. Is it a performance thing, or a songwriting thing, that you're writing to your voice's strengths? How has your practice as a vocalist progressed?

When I first started making music and singing in this scene I was 18, and I'm 26 now. And I'm just starting to feel more comfortable with myself as a person, and getting to know myself, and accepting myself. I think that also, indelibly, has an impact on your voice. Because your voice is like the most vulnerable, naked expression of who you are, in a way. So if you're not comfortable with yourself, you can only fake it so far.

You and I have talked about this in the past, but we both suffer from pretty wicked Imposter Syndrome.

Yes. "Oh, I'm just here because I got this lucky break." Or, "I knew this person who introduced me to this person, and someday they're going to wake up and realize that I'm just somebody who sings, I'm not a singer." You have those doubts. And I guess I've had enough kind of out of body moments, where you step outside of yourself and you look at yourself like anyone else would — I've had this conversation with my mom a few different times this year, like wow: If I didn't know me, and I looked at the stuff I was doing, I would be like, "She's legit." You know? And that's crazy. And my mom's like, "Yeah, that's because you are legit. You have to believe it. It's true." Try to give yourself a little bit of credit for things that you've accomplished, instead of just feeling lucky and like it could go away at any second. Give yourself the chance to say, to some degree it's lucky, and to some degree I earned it. Which is really hard for me to do, and does not come naturally to me, even though I work really hard. I have that natural inclination to be like, "I'm just lucky, and they're going to decide that I'm not good enough."

Do you think that some of that is getting started so young? For me, I started trying to write when I was in my early 20s, and I still feel like the kid of the music journalism scene. Do you feel like that in the music scene?

Totally. In numbers, in a lot of ways I am. A lot of my friends that I really look up to and respect and who are now my peers — I almost said somehow. I was still about to diminish myself. [laughs] Some of my peers are a lot older than me, in the range of 10 to 20 years older than me. So I do kind of feel like the kid. Which is really interesting. Because in the world of pop music, I'm like geriatric at 26. Everybody on the Billboard chart is my age or younger. But in the realm of music that I'm interested in, which is people who are in it for the long haul and take the music itself really seriously, I'm still quite young. So that's definitely part of it.

I think it's a perfect storm of being a woman — we're taught explicitly and implicitly to keep our heads down and not congratulate ourselves too much, not be too confident, not speak too loud. Even growing up with a super feminist mom in New York City, which is the most forward-thinking epicenter of the country, I still was subject to that. So I'm a female, and I am in my 20s, and I did start really young. The thing about being a musician is, that's all documented. All the music I've made while I was figuring it out, people have heard that. It's weird. Up until tiny deaths — and not to discount anything I've done, because I'm proud of all of it in different ways — I don't think I'd found myself as a musician, and I didn't ever really see myself in the work that I was doing. For a long time, I just thought that that's how music careers worked, like you kind of just get taken along. And I just made a conscious decision, when it didn't make any sense for my career, to not do that. To just make some songs for fun, and because I wanted to feel fulfilled musically, and just see what that would sound like.

I really like what you said earlier about being in it for the long haul. It's so tempting in this business, because we tend to go through a cycle of getting excited about something and pushing it into the spotlight, and then a month later we move on to something else — it's really tempting to want to get into that cycle and be that hot thing. What keeps you nose to the grindstone? What drives you creatively, and makes you want to keep focusing on the craft and not the attention?

I mean, I think at a certain point you decide what kind of career you want. Or at least I did. I had to recalibrate the reasons why I got into this. And I don't mean to talk about the Chalice or anything I've done like it was the Grammys or something, I mean it's small time stuff. But it was enough of a departure from any of the opportunities I've had to show a contrast, like a "two roads diverged in the woods" kind of a thing. And I just, for a while, kind of felt lost. Like I completely lost my way and forgot why I did it, and just got into the rigamorale of, like, "this many people need to like this song," and "we've got to get this magazine to write about it." It's so easy to get sucked up in that, because it's like a game, and I think by nature I'm a competitive person.

And honestly, my whole life, until tiny deaths, I thought that I wanted to play arenas and be huge. Those were the kind of ambitions I had, and I told everyone. And that was something that Lizzo and I had in common, actually, in the Chalice. We both wanted to play arenas. That was my blind goal, and not even for any reason, necessarily. I just set my goals as big as I possibly could, and everything I did in my whole life was toward that.

I didn't have the best romantic life, and I don't feel like I even had as awesome of a social life as I could have, because everything was towards that singular goal. To be a big, successful superstar, basically. Which sounds so silly, out loud, now to me.

It doesn't sound silly to me.

It's just always what I thought I wanted. So when the Chalice broke up — I thought I had my life planned out, at least for the next few years. And it wasn't going to go that way. And I had a moment of self-reflection, of just, "What am I doing? And why? And what do I want, and why do I want it?" I spent a lot of time just remembering the moments when I decided to get into music, when I was so little. Remembering the songs. I remember being on a train with my mom and hearing the Alicia Keys record for the first time, because I had heard "Fallen" and she bought me Songs in A Minor. And feeling so moved from song to song, in such different directions — feeling pumped in one song, and heartbroken the next song. I didn't know what any of that was, I was so young. But I wanted to be able to do that for people. To make people feel things... It's all I ever felt compelled to do.

I had a really profound change. I think you have to give up so much as an artist, and also as a person, to be that successful. Your health is neglected, and your relationships are neglected. And honestly, a lot of people who get that successful treat other people really poorly. And step on a lot of heads as their ladder. And I just don't want that. I really came face to face with what it would mean to be what I thought I wanted to be, and what kind of a person I would have to be, and what kind of a musician I would have to be to make those things happen. I just decided that I didn't want it anymore.

Previously:

The O.K. Show, Episode 1: A candid discussion on mental health with Charlie Van Stee

The O.K. Show, Episode 2: Mary Beth Mueller and her one-woman crusade against cancer

The O.K. Show, Episode 3: Adam Levy’s devastating loss and beautiful new solo album

The O.K. Show, Episode 4: Irv Williams, the elder statesman of Twin Cities jazz

The O.K. Show, Episode 5: Lydia Liza on empathy, anxiety, and staying grounded in the music business

The O.K. Show, Episode 6: Hard-touring rapper Astronautalis talks about staying sane on the road

The O.K. Show, Episode 7: Mayda on her health and her journey as a Korean adoptee

The O.K. Show, Episode 8: Manchita on feminism, rapping, and her relationship with Eyedea

The O.K. Show, Episode 9: Lizzo on self-acceptance and falling in love with herself

The O.K. Show, Episode 10: Rock ‘n’ roll dreamer Dan Israel comes to terms with his divorce and his health