I listened to Dessa rap and sing with the BBC Wales orchestra, this month. Her sparkly character glittering about the stage. Her voice has a sensual, draw you in, complex timbre. Her lyrics are complex and playful. She’s written memoir essays about her time on the road, falling in and out of love and the like.

It’s a keen intellect that shines through. One peppered with a life hard and well lived. Touching lightly on mental health and the craziness of forging your own musical path:

She writes in her first essay:

“... Today’s conventional wisdom says that the best way to live a life is to keep all the components partitioned—love, money, friends. You’re not supposed to date your boss, or go bowling with your analyst, or borrow large sums of money from your drinking buddies. We think of ourselves as a store-bought cake with a sheet of wax paper separating all the slices so that they never touch: neat, single servings. But hanging out with Doomtree, it was all one thing—social, professional, romantic. I did all of it with the same people and often at the same time. There were no hobbies and no off-hours, no work-life balance; there was just writing songs and walking to SuperAmerica for cigarettes and drafting set lists and drinking with the guys and making album budgets and goofing off and collapsing into sleep tucked into the leopard print of my boyfriend’s left shoulder. None of it came apart from the rest….”

And on deciding to be an artist:

“...Like a meteor shower, a series of questions flashed through my consciousness at regular intervals: Q: How long should I do this before I give up? Part of the challenge in becoming an artist is that you have to place your bets before you’re fully dealt. You have to assess your talent, still half-formed, and decide what you are willing to stake on it. There’s no best-practice handbook for the pursuit of unlikely dreams. How much of your life should you spend trying to be an astronaut or a fashion model or a professional rapper before deciding it’s time to redirect your energies? A year? Two? Ten?

Some members of Doomtree are genuinely art-for-art’s-sake creative types. Cecil Otter is like that, I think. He’ll emerge from a thirteen-hour production session bleary-eyed and blissed-out by whatever he heard through the headphones. I’ve never been that kind of purist. For me the communication of an artistic idea is fundamental to the endeavor. If there wasn’t someone at both ends of the line, at some point, I’d just want to hang up.

Q: What are the opportunity costs here? I knew that I was capable of making a good living in another field—I had gotten good grades, could interview well, was willing to work hard. If music wasn’t going to be my life’s path, then the time I spent writing songs and bios and press releases might be better spent doing something else—going back to school, or applying for a full-time job, or maybe teaching English abroad, where at least it’d feel like I was contributing. I was a lousy waitress. I was a pretty good tech writer, but couldn’t envision it as a long-term gig. And I couldn’t butterfly forever.

Q: Am I delusional—like, fully out of my damn mind? I’d venture that there are thousands, maybe tens of thousands, of young women at this very moment who aspire to be the first female president. And one of them will be. The problem is it’s impossible to tell if you’re the one. When small children say they want to be quarterbacks or tap dancers, they’re applauded for their audacity. Aunts and uncles toss a ball around the backyard and buy a little fedora for Christmas. When you are a grown-up who says she wants to be a rapper, the blush is off the rose. The conversation at the Christmas table is more likely to include the words compound and interest than follow and dreams. And it is a little crazy to believe that you can navigate a career path that seems to pan out so rarely. The numbers say you’re almost certainly wrong.

Q: Could wanting it badly enough make it real? This question isn’t about hard work—that’s a prerequisite. It’s about taping blinders to your temples; categorically writing off the critics who don’t like what you do; categorically writing off the counsel of the people who love you and worry about how you’re doing, to insist, I am going to will this into reality. This is the Tinker Bell model. She’s only real because she is clapped into existence. The children refuse to entertain any alternative, and the force of their desire and their determination has metaphysical consequences. The Tinker Bell model is the nuclear option. It taps every reserve. It permits no Plan Bs. It’s bold, reckless, conceited, juvenile—right up until it works. And then, in hindsight, it’s brave, windblown, and scored with strings that sustain right into the commercial break. I’ve known artists who’ve tattooed their hands and faces to ensure they’d have no recourse, no desk-job escape chute…”

I’ve heard artists talk about no Plan B. I don’t know how many burn out - an exploding star.

But those that survive are forged into some alchemical metal.

The above passage is some of her least lyrical more business like writing. Mostly it’s cheeky and funny. Rhapsodic with Street smart lyrical-ness and amazing erudition that her rap-cleverness can’t hide. I’m somewhat in awe and a tiny bit in love. This must be what her audiences feel.

She paints faces (dressed as a butterfly) to make money before her music has taken off. The children ask her:

“...Most days, I fielded the same set of questions: Q: Can I get two? “Unlikely. This line is very long. But if there are no blank faces, come back and I’ll do your other side.”

Q: Are you a kid or an adult? The costume made it tough to tell if I was a giant child or just a parent in disguise. “I’m an in-between.”

Q: If your wings are real, then can you fly? “Kid, nobody can paint while flying.”

Q: Is this, like, what you do? Your job? Well, honey, that one’s complicated. Some days I paint faces. Yes, for money. And sometimes I write instructional manuals as an independent contractor. And sometimes I wait tables at a sports bar downtown. And sometimes I work as a temp for an agency like Dolphin Staffing—which is not as magical as it sounds—but at night, I am a rapper at a precarious point in her—

Q: I saaaaid, is this, like, what you do? Your job? “Well, I’m face painting and you’re waiting to get painted. So is that your job? Being second in line to get face painted? Are you a professional paintee?”

Q: Do you have a boyfriend? I do, but only for a little while longer. He’s becoming a famous person, I think, and there is no competing for first place in his heart because that position was already occupied by music-making when I met him. And maybe the best spot in my heart is reserved for the same thing. But all sorts of people want a piece of him now, including beautiful women who I don’t think he has the self-discipline to turn away. And I am a sizzling mess: angry and jealous and vengeful and sad. That’s the truth, but I can’t share it with you because you’re too young and this is supposed to be a party and I’m being paid by the hour.

Q: Do you have a boyfriend? “How come? Are you single? Are you asking me on a day-yate?”

And like the best heroine-quests she ends…

“...Now, years after that first NPR review and my last face-painting gig, I’ll sometimes stand at the edge of the stage during a Doomtree show. I’ll put my finger to my mouth to quiet the room. I’ll hold my mic off to the side, a gesture that will usually send a round of shhhs through the crowd. Unamplified, I’ll yell something like: “Hey, we’re Doomtree. I’m Dessa. That’s Sims, that’s P.O.S, that dapper gentleman is Cecil Otter, and my guy Mike Mictlan is the hero who thought to grab the case of waters from backstage. Here behind the tables, where the magic happens, is Lazerbeak and Paper Tiger. If it’s your first time seeing us: welcome. If you’ve been coming for ten years: thank you. The reason that seven musicians can play a two-hour show to a sold-out room—even though we don’t have a big song on the radio, even though we aren’t in Sprite ads, even though we write pop songs that are eight goddamn minutes long—is you. Our growth has been slow, and if you’ve been here from the beginning, you know that’s true. But because we make our money in ten-dollar increments at that merch table right there—wave, Ander! That’s Ander—we’ve been able to maintain total artistic control. We don’t have to ask a record executive if it’s a good idea to pick the song with a clarinet sample in 6/ 8 as the first single—of course that’s not a good idea—but it’s good art, dammit, so we’re doing it. Doomtree runs on word of mouth and pixie dust. We are real because you’ve said we are. We’re the Tinker Bell of this rap shit. So thank you….”

Read her memoir essays on Amazon here. So many interesting artists still to be discovered by me. Sign up to me monthly newsletter below.

Here’s a Dessa song

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