This month, Dessa is preparing to release her new memoir, My Own Devices, in which she shares the very personal stories behind many of her best-known songs and offers poignant reflections on love, heartbreak, and her life on the road.

In the first portion of this interview, Dessa and I discussed her long on-and-off relationship with the rapper P.O.S, and what it's like to finally share the details of that tumultuous relationship with her readers and fans. In part two, we discuss turning grief into art, the gendered expectations that we create around an artist's ability to be vulnerable, and her entrance into the Twin Cities hip-hop scene in the early 2000s.

Andrea Swensson: I want to talk a little bit about the grief process. You have a song, "Good Grief," that I find to be very powerful. Something that I’ve reflected on in recent years is that there’s many different ways to feel sad; you described it as running a little blue. To me, when I experienced the loss of a family member – and I know you talk about losing your grandmother on your most recent album – going through that grief process really opened my eyes to how dysfunctional the depression in my life had been. I’m wondering if you found that experiencing grief recently, in losing a family member, put other kinds of pain that you’re experiencing into a new perspective.

Are you saying that when you were grieving a family member that it felt productive and important, which threw into contrast the other kind of depression?

Exactly. There was a healing element that you could actually put behind you, as you say – "good grief is the one that’s in your past." In the context of thinking about this ongoing heartache and then also your mood disorders that you talk about in the book, did it make you think differently?

It's so not woke to be like, nah. [laughs] But maybe that’s a revelation I’ve got ahead of me still. I don't know that I’d describe it as the most emotionally healthy way to conduct one’s self, but I think for me it’s been trying to figure out – well okay, I’ve got this grief lying around. I wonder if I could make a quilt! It’s like, what can I do with this? You try to feed it into the machine so that it does maybe something more than just hurt. I don’t subscribe to the idea that grief is sanctimonious, that anything that doesn’t kill you makes you stronger. I think sometimes a lot of things that don’t kill you leave you seriously compromised and weaker. But to say okay, is this a resource that I can burn for heat? Or turn into a song, or some way render fuel for a bigger ambition? I think with a lot of negative feelings – I’m reading Kitchen Confidential, and [Anthony Bourdain] talks about how many of his biggest achievements are fueled almost exclusively by spite. It’s repurposing something for fuel.

Something I was thinking about as I was reading this book is you’re so vulnerable –

[groans] Cool.

Or should I say — you’re so brave.

There we go. Can we print that?

For real, though, we’re seeing a side of you that has not been revealed before.

Really? I feel like – I can’t tell. I guess I don't know. All my songs aren’t, like, battle anthems.

That’s true. But what I was thinking about is that as we’re getting to the more secretive, softer side of Dessa in the book —

[chuckling]

You’re coming out with these songs like "5 Out of 6" and "Fire Drills," where you’re so fortified. And I’m wondering if, in the process of investigating this personal turmoil and opening up and sharing all these things about your pain has allowed you to channel more strength as well.

Yeah. Do you remember the movie 8 Mile?

Yes.

You know how Eminem essentially battles himself and there’s just not much left for an adversary to do?

Yes.

I do think there’s something sort of freeing in outing your own secrets because like now what are you going to bust me on? I’m pre-busted. And thinking about vulnerability — I think it’s also interesting how the voice informs our understanding of the message. Some of the stuff that Drake writes is like baby-thighs soft, but it’s Drake. Whereas I do wonder if we’re predisposed to detect and flag that vulnerability a little bit more when it comes from an academic or a woman. Sometimes when you hear that – what was that song about his mom that Kanye wrote? That’s an area where you have a person we anticipate will be tough being tender. It’s like, Shut up; Kanye has the floor and he has something important to say. And then when you have someone speaking who you anticipate is going to be more emotional, like a woman, it’s like, well you would.

It makes me think. There’s this trope that in hip-hop there’s all this bravado, which kind of implies that it’s a façade. But I feel like, listening to your most recent album, you’re tapping into a strength that goes far beyond bravado. "I’ve been vetted, uncontested"– like you're untouchable now, because of what you've been through. 

Let’s end the interview here, this is a very high note. Thank you so much. My meter is expired. [laughs] With the song "5 Out of 6," that one was slow to come together. I was walking around and wrote four sets of lyrics to that beat. And I was like, is it a tender song or is it a tough song? I’ve already written a lot of tender songs. I want this one to be tough. And then, I realized that I privately don’t actually think that those are mutually exclusive, although in shorthand very often we depict them that way. To say to someone “I’m sensitive as hell and I would like to fistfight you” — I like that.

I like that too. Something I wanted to ask about, which shows up early in the book, is your entrance into the local hip-hop scene. It makes me think about how, in "Fire Drills," you talk about being "the vixen of the wolf pack," and I don’t want to put too fine a point on it, but you were one of the only woman in this big scene for quite a while. What kind of feedback were you getting as you were stepping on stage for the first time?

Varied. On one hand, it can be easy to dismiss someone – like when I went to Scribble Jam for the first time, I was greeted by a rapper that I admired, who asked if I was the model selling Doomtree merch. He wasn’t being mean. He was just confused, because there weren’t that many women involved in the scene then. So that’s an innocent mistake. There are less innocent mistakes, for sure, to be made. But also, I was the beneficiary of attention, and that’s the biggest thing that you’re looking for as a beginning artist. Because I was unusual. There was a novelty. For a woman’s voice to boom over the PA might be enough to interrupt a conversation at the bar and turn a head. And that is the quantum unit of success: just a little bit of attention gives you an opportunity to turn that moment into an audition, gives you the opportunity to turn that set into a real connection with a new listener. So it cut both ways, but I’d say in the beginning I benefited from it more than not.

I was also – I didn’t know it at the time, but I was also struggling with some not-very-progressive ideas about women in hip-hop, too. When I look back at the bios I used to write myself, I flinch and cringe. I think I was one of several if not many women who might’ve privately congratulated themselves on the ability to roll with the guys, which is not a way of thinking that forwards egalitarian ideas, or invites more women into the community.

I just had this flashback to P.O.S. putting out his Rhymesayers debut, Audition, in the Entry in 2006. And there was this moment where — I don’t think I knew that you were performing that night, and it was really sold out and crowded, and all the guys were on stage, and you just popped out of nowhere like a little wac-a-mole. I was like, Who is that?

Do they know she’s there? Is she supposed to be there? [laughs] Yeah.

It was something that I got really excited about, seeing you onstage and seeing you hold your own among all this male energy. That was 12 years ago. There’s so many more women involved in hip-hop in the Twin Cities. Do you see a role that you played there, making way for other artists?

Legitimately and honestly and truly that has never occurred to me until right now. I would be very flattered if anyone in the Minneapolis community saw the work that we were doing together in Doomtree and was encouraged to get involved. That would be really gratifying. Obviously, when I was around there was Desdemona, who was working more in the spoken word realm. Psalm One was in Chicago doing her thing. But to be honest I see fewer women on the national stage now — although you’re right, I feel like there are more here. And by national I mean well above my head – more rarefied air than mine. How many female MCs are really killing it? I think there are not that many.

We still see Nicki pitted against Cardi B, too; there’s that happening in that stratosphere. There can be only one.

Yeah. Exactly! It’s Highlander.

When I was watching you perform at Orchestra Hall, I was really taken by the sound of your voice in that performance. I felt like you were tapping into something almost guttural, like it was coming from a new place. I’m wondering if the process of reflecting on all this heartbreak, and exploring neurologically how to get over this romantic situation – do you feel like there were physical changes that occurred in that process?

What an interesting question. Part of me thinks that, lifestyle choices aside, my voice is just older and I happen to like it more. You can hear it even now – there’s a little texture in it that I didn’t have when I was younger. When I was young, in my early 20s, I was a heavy smoker and I would smoke a bunch of cigarettes and sometimes scream outside to try to get texture in my voice. Part of it was that the entire genre that I enjoyed listening to, with the exception of maybe Sarah White in Minneapolis, the instrument is male. And I don’t have that instrument. So I’m trying to figure out how to play a cello suite on a violin. And I didn’t like that. I wanted a bass-y, powerful voice. And so I feel like now that I’ve spent those years alive and also spent those years living the way that I have, with a lot of grief and yelling and some great whiskey and some awesome fun nights and some lousy late nights, yeah, I like the instrument a little more. And I’m sure there’ll be a diminishing point of return. One day I’ll like the instrument less. But right now I enjoy the reed better than I did when I was 22. It was slippery then, and I think it’s got grip tape now.

There is a line early on in the book where you talk about your ambition, and I love the way that you describe this — that you were "walking around with a jet engine under your arm, looking for a plane." You were born with this natural drive, and you didn’t quite know where it was going to go, and you ended up pouring a lot of that into Doomtree and really focusing your ambition in that area. Now that you’re 15 years into this process of being an artist, what is fueling you? What is fueling that jet engine now?

In some ways I think the feeling and the phenomenon hasn’t changed all that much. I don't know if it stays fed. It’s like a dog. You just have to keep feeding it because it’ll yelp. I don't know why I have that. Do you have that?

Yeah.

I feel like its appetites can change, but the hunger doesn’t, right?

Right.

So right now, I’m feeding it a book. Next year I’ll have to hunt something else.

I so related to the part where you said as a kid you were envisioning yourself as this stressed out middle-age person pacing around late at night with Chinese takeout and trying to solve whatever you’re working on. And I had many of those moments when I was working on my book, where I felt like I’m finally doing it. I’m pinning up notes on the wall and going crazy at 2:00 in the morning, and maybe this is it.

Yes. I had exactly that feeling when I was doing some of the brain research that you mentioned. I would have these flashes to the camera angle above my shoulder, and I was like, I’m her! It felt so good. Feeling purposeful is a high that’s hard to get elsewhere.

Microfilm machines really helped with that imagery.

I know. That’s my next kill, is I haven’t still messed with microfiche or microfilm. That, or kickboxing alone at night.

To end with, I'd love to assess where you’re at right now with all your various projects. You talk a lot in the book about moving to New York – and if the successes you've experienced like appearing on the Hamilton mixtape are going to be enough to sustain you out there, where it’s very expensive to live and work. Where are things at with you?

Rent’s paid. Right now, I think, like a lot of musicians, it probably paints a sunnier picture on my social media than the picture I live in, and that bothers me. I think the trick is that after a hard show I don’t want to hurt anybody’s feelings who was at the show, to be like – Springfield; tonight sucked. I’m really tired. Because that’s not nice. Now that I’m off tour, I'm looking for ways to be a little bit more honest or at least representative about the way that I present myself onstage, or in the public is important to me.

I feel happy and proud that the book is coming out. I really do. I’ve wanted that since before I knew about Doomtree. I’ve wanted to be a writer since I was in my late teens and early 20s. So that’s gratifying. At the same time, one of the pieces of counsel that I’ve consistently received is like you will be bummed right after this thing comes out. So the best counsel that I’ve gotten is sink your teeth into something else now so that you’re not relying on this old work. So right now I’ve got a couple shows coming up with the Minnesota Orchestra in October, and then I’ve got to figure out how to do book tours right. So those are the two artistic projects that I’m focused on. And then I think it’s time to go back in the lab and stop talking about art, and make something again.

Do you think music is the next – or another book, or both at the same time?

I’ve got maybe a third of a manuscript of fiction done. We’ll see if anybody’s interested in it. And then yeah, Lazerbeak and I chatted on the phone last week about getting back in the – nobody says “lab” anymore – going back to our respective basement studios to start work on music again.

Thank you so much for talking to me today, and thank you for this beautiful book.

Thanks for the thoughtful questions. This is a different degree of candor, so it’s nice to do it here with the Current. Thanks.

Read part one of this interview here. Dessa's memoir, My Own Devices, will be released nationally on September 18 by Dutton Books.