An interview with writer & rapper Dessa

Dessa is a rapper, singer, and writer who’s made a career of defying genre conventions and audience expectations. As a musician, she’s collaborated with full orchestras, contributed to The Hamilton Mixtape on the invitation of Lin-Manuel Miranda, appeared on the Billboard Top 200 charts, and toured five continents. As a writer, she has contributed to The New York Times, National Geographic Traveler, and literary journals across the United States.

She recently joined me on IG Live to talk about navigating this time as an artist, her writing process, her tips for the business side of being an artist, and more. An edited version of the conversation is below.

Four questions for Dessa

MC:You are typically on tour all the time and it’s come to a halt. What has that been like on an emotional level and practical level? Can you share how you’ve pivoted some of your efforts during this time?

Dessa: Yea, I think a lot of creators found that there have been distinct phases. In music, when the shutdown first happened everyone was trying to guess – how long is this? Should I unpack my suitcase? Should I cancel one month of shows – or all my shows? I think for me, I had something like 12 months of shows canceled…all told. In those first few months, I started a weekly poetry/performance on IG Live, doing readings and Q&As. I did that for about two months. Now it’s sort of brainstorming time again – some new writing, mind mapping how new short stories might unfold. Trying to take some of this time to write new material, but also taking the time to be sad and afraid. We need to be forgiving, if you’re not crushing it every day. There’s a reason why your productivity might be tapped. It’s scary. It’s ok to just be a human being for a while and not feel like you’re failing to make the absolute best use of this time.

MC: You do so many things as a musician and a writer. What strategies do you have to balance them? Do you focus on one at a time or simultaneously? How do they intersect?

Dessa:While I was growing up I fell in love with language. I graduated college, but then I didn’t know how to get a job as a professional writer. It felt easier to make an entry into music. Even if you can’t find a paying gig, you can find an open mic–like, there’s at least a visible path into the form. It was after competing as a slam poet that I would up in music. And only after I’d built a career in music, was I in a position to finally get a book deal.

MC:Do you have a writing routine and if so, tell me about your writing process for songwriting and prose?

Dessa: I admire but don’t aspire to a really regimented, structured schedule. For me, the size of the finished piece really determines the process. For the shorter stuff it can just be like “write and see” what sounds cool… but for the longer form stuff…you have to make sure, and plan and stress test that material first. There are three distinct phases: the gathering of the raw material, drafting the thing, then the editing. Letting it sit allows you to be the closest thing to being a reader of that work — it enables you to really edit more effectively.

MC: You’re very savvy on the business side of your art. What tools do you utilize to help you get there?

Dessa: I think I’ve been lucky enough to work with people who I trust, and who really like art. People who are not just pressuring me to try and take shortcuts to be profitable. And, who are my friends. That said, when I’ve got an eye on a particular opportunity or we’re drafting the terms of a deal, I really try to figure out what’s in the other person’s interest. If I want a reporter to feature my work…well, what are the reporter’s interests? They’d probably like a good photo so they don’t have to go online and search for one. So, anything I can do to make it easier to work with me, rather than harder. Everyone has a job, so how can we work together, figure out how to craft mutual wins so that when you win everyone who works with you wins, too?


Watch the full interview on IG Live here.

Leave a comment to this article