Fell in Love with the Struggle: A Roundtable with 17 Rap Writers

We spoke with 17 writers about the ups and downs of the creative life.
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Rap Writer Roundtable, 2019

This wonderful field I work in grows more and more uneasy by the day. Because of the Internet, words are no longer quite as premium. If anything, we have too many words; we see gobs of them in clickbait articles, YouTube video descriptions, and Twitter threads. Writing has never been more common; saturation is everything. But writing is still just as important today as it ever has been.

In an effort to take the pulse of music journalism in the social media age, I've compiled interviews with 17 music writers who are either on staff or who have freelanced for a music publication. This effort was coordinated with the help of Brian Zisook, the Editor-in-Chief of DJBooth. What follows is a synthesized conversation based on the best moments from my conversations. All of the writers featured are either entirely or partially hip-hop writers: that is, writers who communicate the world’s most popular—and word-oriented—genre.

I hope this piece inspires the “average” reader who is curious about the individuals behind the articles they read. I hope hip-hop fans view this as further evidence that the spirit of the genre—the stories, the words—do not end with the music. And I hope this content speaks to up-and-coming writers; as a guidebook wherein a writer can learn from the best in the blurry, discombobulated business which they seek to enter.

What are your earliest connections to hip-hop?

Armon Sadler, ELEVATOR: Like anyone, I’ve been a lifelong fan of hip-hop. My dad coached football and so my brothers and I, we’d all drive to practice together, and my dad would play old 50 Cent, Mobb Deep, JAY-Z. In thinking back on some of the biggest moments in my life, I can remember exactly what I was listening to at that moment. I can remember which Drake album came out at a certain time; Nothing Was the Same dropped my freshman year at Cornell. That was my soundtrack walking to class, going to the gym, doing homework late at night.

Mark Braboy, freelance: I can remember as early as 11, I came across my first issue of The Source. It was an issue featuring Eminem, long before the Benzino beef, probably around the time of the first Marshall Mathers album. I used to always read the reviews, and I would think “Wow, that’s something I wanna do.”

I got into writing through poetry. There was this girl I liked in high school; she was pretty, tall, and thick. She used to write poetry and I always had respect for people who pursued the arts. So to impress her, I started writing a little poetry. This poem called Mistress Number Nine, she was digging it. I was on my Lil Wayne shit from thereon out when it came to poetry. I wouldn’t even eat school lunch sometimes, I was so busy writing.

A. Harmony, freelance: Since I was very young, I always wrote about things at large. I was also always musically inclined. They were two separate passions that kept growing in their own right, but writing about music gave me a way to marry the two. Storytelling is a natural passion I have; I love to learn about all the artists and what their stories are. A singer has their voice, maybe a musician has their ability to play, but a hip-hop artist, the first thing they have is their story.

How did you get your start in this business?

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Donna-Claire Chesman, DJBooth: My writing career begins with Jeff Weiss, the patron saint of hip-hop writing. I e-mail him in the middle of the night, I’m like “Let me write for you.” And he agrees! [Editor's Note: Donna-Claire had been writing online for a while; if you’re gonna e-mail Jeff Weiss, make sure you have clips.] I had to rewrite that piece 14 times. I couldn’t get the intro right; it was 300 words. I had this incredible ego death; I thought my life was over. After that, I never had to rewrite anything 14 times again.

Then I have this dream that I write this piece for DJBooth about Tyler the Creator’s coming out story and my coming out story. I wake up, I roll over, I pitch to Z, I go back to sleep, I wake up, and he takes the pitch. And he’s been stuck with me since.

Lauren Kruis, These Days: It wasn’t until this past year and a half that I dove into writing about music. I took a chance and reached out to several Chicago publications, and eventually found my place within These Days News. They gave me the freedom to find and profile up and coming talent. Finally, I was able to combine my two passions, writing and music, and shed light on some of the immense promise that Chicago holds.

Shane Ryu, freelance: After graduating college, I was kind of stuck in limbo after working full-time for a few years, and I was getting sick of the same rinse-and-repeat schedule. I had always entertained the idea of starting a blog, but that didn’t come to fruition until I first listened to Kendrick Lamar’s DAMN., and that Eureka moment led to my first written piece about music. After the EIC of CentralSauce reached out to me, all of my focus shifted there. In the process, I learned that writing about hip-hop filled a void that nothing else could up to that point, and I’ve been chasing that high ever since.

How are you able to make ends meet in a field that doesn’t pay well?

A-Harmony: I use the website whopayswriters.com to get a sense of what the publication’s budget might be.

Wanna Thompson, freelance: At this moment, I’m owed $2,040, and I still have no idea when it’s coming. I’m fortunate that I have another job. I work 9 to 5 and it’s a pretty good job, they have benefits and stuff. It’s kinda hard because I have to stay up after work and write till morning, but it’s worth it.

Gary Suarez, freelance: Before I wrote full-time, I did marketing work, I worked in offices, I managed employees, I had budgets and did the sort of stuff you do in there. That also allowed me on the side to do the writing I did and not have to worry about “Where’s my health insurance coming from?” or “How am I gonna pay the rent this month?”

Mark Braboy: I’ve worked solely as a writer for about two years now. In a good year, you might get those good blessings, those good headaches where you got so much going on; and then some seasons, there isn't much shaking. You might get a feature piece here and there.

Donna-Claire Chesman: I have to underscore that I’m exceptionally lucky to be the managing editor at DJBooth and it doesn’t always go this way for a lot of people. And some people work really hard for a really long time and nothing will happen. I’m supposed to say “If you love something so much, it’ll work out.” I don’t know that to be true.

Dart Adams, freelance: If I had to rely on my income as a writer to live on, I’d likely be homeless and dead by now.

Have you noticed inequality in the way marginalized people are compensated and treated?

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Mark Braboy: Being a male hip-hop journalist and being a female hip-hop journalist are two very different experiences that come with two different lenses. I’m six feet, 300-something pounds. I always get talked to professionally.

Wanna Thompson: The other day, someone was having a conversation about freelance rights and how much money they get paid; there was a significant amount of people that were white that were saying they get paid an enormous amount of money for the same word count or subject matter, and that made me feel like wow, are we getting the shit end of the stick? We’re not getting treated the same way everyone else is. After I talked to more black creatives and they told me these things, it was very alarming. We shape the culture and rap is a very black cultural experience... It’s interesting how we’re being shortchanged.

A-Harmony: You don’t realize it until you’re having conversations with others and you’re like “Hey wait a minute, I’ve been doing the same amount of work for less money.” It’s tricky as a freelancer, especially when you’re just getting into it, where you stand or what you should be charging. And I think as women, we often have difficulty asking for what we want and being vocal about those things, especially when you’re new.

Gary Suarez: Things are better now, but it’s still largely—especially at the publications that people wanna write for—white male cisgender people who run the show. Some of these people do want to include diverse voices and deal with these issues of marginalization and exclusion. But at the same time, being diverse is what’s cool now… “We do this piece about Bad Bunny, let’s make sure we have a Latinx person writing about it.” That’s where we get into it.

I appreciate any work that I get, but I recognize that I get to write about these artists because they are looking for someone to be authentic on it. I speak to a lot of my fellow Latinx music writers... The one thing with all this is “Great, I’m so glad we’re getting these bylines, but at the same time, I don’t just want you to only call me when you get a chance to talk to J Balvin or Fat Joe.”

How does working in music journalism affect your mental health?

Mark Braboy: Man, last year was one of my hardest years. It’s like you’re holding—sometimes you’re just holding the floodgates and all that from publishers… Sometimes you may get a reply, sometimes you may not. You’d be lucky if you get a rejection email from a lot of places, to be honest.

Masongo Ogora, freelance: I stopped writing due to becoming depressed from rejection and feeling inadequate in my personal and professional lives.

A-Harmony: I said yes to so many assignments. I was burnt out… I wasn’t getting a lot of sleep and I’m juggling a lot of assignments and there’s only so much you can do before all areas start to suffer. If you are just as diligent about your free time as you are about working, I find that it balances itself out. But you really have to be your own advocate when people try to encroach on your free time; you have to be your own disciplinarian in terms of not working when you shouldn’t be working.

Wanna Thompson: I started taking writing very seriously as a career last summer and honestly, I’ve wanted to give up a billion times. It’s really, really annoying.

How much does social media factor into your practice? Is it too important? What about the mental toll?

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Riley Wallace, HipHopDX: 2018 had a lot of arcs and storylines. There was a lot to follow, and sometimes—especially being a parent—it becomes all-encompassing. It’s not a profession that breeds millionaires, so it’s definitely something that can wear you out and strain relationships. Particularly if your interpersonal relationships aren’t as focused on the happenings of the culture as you are at all times. It’s hard to turn off.

Gary Suarez: I’m on Twitter all day. Currently, I use tools like Hootsuite and Tweetdeck, so I can have multiple columns and feeds to look through. If I deleted my Twitter account tomorrow, I would lose thousands of dollars of work in short order, and I would not be able to recover that.

Masongo Ogora: I literally live and breathe social media and I fucking hate it.

Mark Braboy: Twitter is like the streets. You're walking around Newark and you gotta keep that strap on you at all times. It can be toxic because everybody wanna be a name, everybody got something to say, whether it’s justified or not. That harassment that Wanna dealt with, I thought that was sickening.

Donna-Claire Chesman: I think Twitter can be a fun game if you approach it the right way, but you have to divest from these things to maintain your sanity. I think a lot about Craig Jenkins, and I don’t ever wanna see his Twitter mentions. Because he’ll fire off one tweet and people will just attack him.

What advice would you offer up-and-coming writers?

Gary Suarez: The advice I’ve often given to folks who wanna write and get paid for their work is they should get a day job, or a night job, something else to be the primary income as they develop their voice and their bylines and make the connections. If you’re coming into this and wanna make a go for it, good for you, but you’re in a hugely competitive marketplace with established relationships, and people are not just gonna reach out to you because you sent a pitch. If you can live with your parents, live with your parents.

Darian O’Neil: Take advantage of Medium. Publications are record labels and you are the artist. Medium is a platform that allows you to skip over the middle man and publish work whenever you want.

Justin Sarachik, Rapzilla: Depending on experience and if you're just starting out, take whatever you can and don't limit yourself to topics you cover. You have to build up that clip resume.

Nicolas-Tyrell, freelance: Mean what you say and say what you mean; have your own opinion, not the internet’s.

Riley Wallace: Never get discouraged. You have to love writing, like really REALLY love it. It shouldn’t be something you do for free as a professional but should be something you could do for free if that makes sense. Never underestimate the power of networking. Keep finding pitches that help distinguish your writing and value. A little-known secret: I actually landed ninety percent of my writing gigs by tweeting the editors. 

A-Harmony: The two most important things in terms of advancing your career as a writer; A. it’s the quality of writing and B. it’s the connections and relationships that you’ve had. Every single opportunity I’ve had comes down to the relationships I’ve made. 

Armon Sadler: Writers really can relate to each other and hold each other down. Don’t be afraid to put yourself out there. Shoot people a DM, send people a message saying “Hey, that was really cool.”

Donna-Claire Chesman: Everyone starts writing. But very few people continue. I think we really undersell what counts as writing. Writing is when you listen to the album and you’re like, “That’s interesting.” That’s writing. You’re a writer; in that moment. So hold onto that and don’t stop doing it.

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