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A candid conversation with Dessa about her powerful new memoir, My Own Devices (Part 1 of 2)

Portrait by Nate Ryan/MPR
Portrait by Nate Ryan/MPR

by Andrea Swensson

September 10, 2018

Have you ever been so hung up on an old flame that you've contemplated using experimental brainwave technology to extract your love for them from your thoughts, Eternal Sunshine-style? Or wondered what it would be like to tour, perform, and make art alongside someone who you know you can no longer be with but who nevertheless has a stranglehold on your heart?

These are just a few of the deeply personal topics explored in the debut full-length book from Dessa, My Own Devices, which is being released by Dutton Books on September 18. Readers don't necessarily need to know anything about Dessa's music to appreciate the impact of her stunning prose, but a familiarity with her lyrics only deepens the experience of learning about her lengthy on-and-off romance with a member of her rap crew ("We're lived too long, too close/So call off your ghost"), her relationships with her glider-pilot dad and environmentalist mom ("My father was a paper plane, my mother was a windswept tree"), and her relentless creative drive and ambition ("Turning my fingers in the sockets, my daily dose of lightning/Just buzzed enough to get me climbing up the kite string").

The book opens with a revelation about said romance and only gets more intimate from there, pulling the reader along for a ride through the inner-workings of her busy mind. When I finished reading it for the first time — which I did in a single sitting, unable to set it down — I already had a notebook page full of questions I couldn't wait to ask her. Dessa and I sat down earlier this summer for an extended conversation, and I appreciated her willingness to speak so candidly about her experiences.

What follows is part one of a two-part interview, which aired in the second hour of The Local Show September 9.

Andrea Swensson: I have so many things that I want to ask you about this book. I found it to be so powerful and brave, and it’s so deeply personal. How does it feel right now, to know that a lot of people are about to read this?

Dessa: I’m tweaking out. I’m totally tweaking out. I don’t think you can do a collection of true stories and make it interesting if you only make yourself look cool. I don’t have any interest in telling secrets for the telling of secrets' sake, but unless you make yourself vulnerable, then there’s no stake. Why would someone care?

Just to address the big elephant in the room right away, the book begins with this revelation that many of your songs have been about the same person, and that we know who this person is here in the Twin Cities music community. And that it is a member of Doomtree: P.O.S. What is it like to finally have that out there, after over a decade?

I think it might be difficult for me to know how we appear from the outside, in the same way that you are so intimately familiar with your family dynamics, that if you could hear your neighbors on the left and on the right describe your family you might be surprised by some of their account. I’m grown. I’m in my mid-30s, working on late-30s. Like most people, I’ve had big romances and I’ve been lucky enough to have them with some amazing people, and because of the job I do those romances have found their way into the work that I make. So in some way, it’s like I’m used to talking about feelings, but in another way I’m not used to talking about the details of those feelings. In song, they’re more or less couched in metaphor, so you can be serious and vulnerable and open, but you’re not really providing the same kind of deposition about the days and months and years that led to those feelings.

I was really struck by how deeply woven this story is with your origins in the music community and beginning to rap and joining Doomtree — and, as you’ve described it, it’s not compartmentalized at all. You were living together, you were working together, you were romantically involved. It’s interesting for me to think about the fact that you have been able to publicly compartmentalize it for so many years. Can you talk about that?

I used to date P.O.S before I was in Doomtree, and then joined Doomtree, and we were then in our early 20s. I think that even when things got difficult between us, and they did get very difficult, both he and I were loyal to this idea of this crew, and it felt unusual, it felt lucky to be a member of it. And I think both conscience and pride prevented me from wanting to poison that well, in the same way that if you’re on a road trip with your extended family and you’re also with your partner and you guys have been fighting, you are naturally disinclined to let that foul mood infect the van. It’s like that — except you’re on a road trip for 10 years. It’s like, I don’t want to bring other dudes in Doomtree down. I don’t want to ruin the tour. I don’t want to make things lousy. So one of the things that I’m proudest of in my life is that I didn’t tear that down. One of the things that is hardest in my life was not tearing that down.

You wrote a bit about being in the van, and that you knew which seats you could sit in to avoid each other’s eye contact in the rearview mirror. How did you get through that? What was that like for you?

I can’t speak to his experience, but I found it very difficult. The flip-side of that coin is wow, being in Doomtree and being onstage and being on tour as an independent musician who is answerable essentially to only her own tastes and conscience must be so good that it is worth doing that. I don’t want to say it’s a privileged problem, because I think people suffer heartbreak whether they’re broke or rich or in politically stable environments or not, but obviously, to put it in context, this isn’t the biggest tragedy. This is one person trying to sort through her tough and volatile feelings, but trying to do so privately while in a public spotlight.

I think the reason that it resonated with me so deeply, and I believe it’s going to resonate with a lot of people so deeply, is that there’s something very universal about this experience of being in love with somebody that you’re not supposed to; that’s it’s not going to work out but you still can’t move forward. And it deepened my connection to your music, and to what you've expressed there. Does that make it harder in the future to address this in song, now that people will know what it’s about?

We’ll see. I have been excited, because I’m proud of the work, to put it out, but also nervous because it’s a candid account. I was talking to Sims a couple of months ago, he read many of the essays, and I was telling him that I was apprehensive and so much of my personal life is going to be out there now, and I was a little bit embarrassed about how that might play in the Minneapolis hip-hop community. And he goes, “Oh honey, no one in the Minneapolis hip-hop community is going to read this – not that many people are into creative non-fiction memoir collections.” So I don’t exactly know how this will affect my life here. I know that my audience as a rapper and as a writer are connected, but they’re not perfectly overlapped. I don't know what to expect.

You don’t think Doomtree fans will pick this up just to —

I think a bunch of them will, but I don’t think all of them will, so I don’t know the extent. I don’t know how much of Doomtree is going to read the whole book. [laughs] We’ll see.

You talk in the book about having a meeting somewhat recently with your crew about needing to take a break. Can you update where you’re at with being a member of Doomtree, and where you see your relationship with the crew right now?

I’ve never been married and I’ve never been divorced, but for me the closest that I’ve come to an experience like that has definitely been this, and trying to figure out how the dissolution of a romantic relationship affects all your other personal and professional relationships. I mention in the book the idea that living outside of Doomtree as a musician felt not only untenable but just totally unappetizing. I couldn’t even imagine at that – this is maybe two and a half years ago – I couldn’t even imagine what that would be like. My entire adult life, almost, has been as a member of this crew, and, as you might imagine, that feels different than saying I’ve worked all of my life in Target corporate. These are people you sleep next to and you get tattoos with or don’t, and you get bad news and good news together, and sweat into each other’s clothes. It is chosen family.

We were finishing off the cycle for All Hands, and by “cycle” I mean the touring cycle. I was feeling just really ground down by all the time partitioning my feelings and trying to tamp them down so as not to have a meltdown. And when I mentioned to the dudes that I could use some space – they were really cool. I had already braced myself for all these arguments, and I knew exactly what I was going to say and I had such clever things to say, and I had no cause to deploy any of that fantastic wit because they were compassionate. When I joined Doomtree I had been a big advocate for official contracts because I’m Type A, and I thought that’s what you did. But now, for all of us, Doomtree has become this entity that you’re in until you say you’re not in, and you can decide the degree of intimacy and the degree of involvement that you want. And now I’m excited by the prospect of upcoming crew shows.

At some point the crew solidified. In the beginning there were members coming and going – MK Larada for example. At some point it became the seven of you. Is that lineup permanent?

Sure. I think it is, yeah. We used to be 12 when I joined, and it wasn’t so much that people were coming and going as much as it was just some of us were lifers, and some of us, including MK Larada – he was a founding member, a huge part of the Doomtree brand – like if listeners know Doomtree’s music, our logo is an X-ray set of teeth with wings on either side, and it’s MK Larada’s dental X-ray that is that logo. I couldn’t overstate his contribution. So we started as a solid 12, and then as people decided to pursue different paths, we have become the seven that we are. I would be surprised if that number changed. I can’t say for sure, but I think we’re a solid septet.

I want to ask you one more question specifically about the big revelation. You mention in the book that your lives are so intertwined here in Minneapolis that it became difficult to be here, and you wrote of hearing your song and his songs on the radio. It made me wonder what it is like to express something like that in your work. It’s one thing to say it once, put it in a book or put it in a song and go in the studio and record it. But then to get up onstage every night and have to revisit these feelings —

Maybe I’m just daft, but my mom and other friends have suggested that hey, maybe you could move on more if you weren’t constantly re-digging the trench you’re living in nightly by singing these songs. Maybe that’s true. For me, I don't know, the song becomes its own thing, that it doesn’t feel rote, it doesn’t feel like an act, but it’s almost like it feels sometimes a bit divorced from the circumstance from which it arose. And maybe that would feel different if I were saying particular facts in all my songs, but at least for me, very often they’re crafted quite a bit, so I’ve got extended metaphors and subjects. That’s the kind of stuff I like. So even a song about heartbreak, I can imagine that being my story with my ex; I can imagine that being a more recent breakup if I’ve had one; I can imagine that applying to the dissolution of a friend’s marriage, and kind of tap into that general wellspring of feeling without necessarily revisiting my particular circumstances. The same is not true when I listen to his music.

That makes sense. I suppose as a performer you’re also thinking of the technical aspect of what you’re doing.

Yeah, and also, to be honest, for me anyway, I go into a very split brain mode where half of you is in performing and half of you is taking metrics – how many people have their cellphones out, what’s the noise like at the bar, where are the stage lights, is your guitar out of key or are you out of tune? But yeah. I’ve been lucky enough to date in a meaningful way at least a couple of musicians here in Minnesota, and that’s part of the deal. The hard thing is watching talented men who are professionally charismatic sing sad songs to break your heart. The lucky thing is dating talented men who are fantastically charismatic and who also understand and give you access to their lives for art. Dating two songwriters here in Minnesota, we all said yes to one another. Like if you make a good song, I will happily forfeit my little slice of privacy for that to be aired because the song is really more important than the blush that might have listening to it.

This book talks about many of the different relationships in your life, and I love the way you write about your father and his glider plane. That chapter is so beautiful — and it suddenly makes so much sense why we hear about kites and wings and birds in your music. Can you talk a bit about that, thinking more about that relationship and the way that it applies to all these metaphors that you love to use in your art?

My dad looms pretty large in my life and in my imagination. He embodied a lot of the things I wanted to be. He was very involved in a lot of passion projects, so sometimes his attention could be hard to get, which made me want it all the more. He built, with hand tools, a plane that he really flew, out of wood and fabric in our garage, and it took a really long time. The fact that he was so driven to do that; for him I think it was an act of dedication, discipline and also poetry. He was later on Newton’s Apple, that TV show on public television, and he talks like he’s got a room full of scriptwriters and he always has. So when they asked him what it’s like to fly, and he’s like, “There are great men in history, da Vinci among them, who would give their right arm to soar unencumbered on the breeze..." and he could just go on like that, indefinitely.

He was a professional bird, essentially. Gliders don’t have motors, and so his job essentially was to find sources of lift, meaning thermals, which are rising columns of warm air, and to spiral up them to gain altitude, and then to soar to the next one and corkscrew up that one, too. That’s sort of a magic thing for a dad to do. He’s been really passion-driven his whole life. He digs science, he digs humanities, he can rattle off a little bit of Latin or talk to you about WWII submarine technologies. He’s got a pretty serious temper, which freaked me out as a kid. His iconic place in my mind, I think, will always be like a figure that I run past new ideas, even if I don’t ever talk to him about them in real life.

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

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This activity is made possible in part by the Minnesota Legacy Amendment’s Arts & Cultural Heritage Fund.