A Conversation With Jessica Lipsky, NYC-Based Culture And Music Journalist
On writing her first book, sharing freelance writing rates, and listening to live music to get in the mood to write
Jessica Lipsky is an editor and reporter based in New York City. She covers music, culture, and politics, and has written for publications such as Columbia Journalism Review, Newsweek, the San Francisco Chronicle, NPR, and Vice. Jessica is also a DJ who spins soul, funk, reggae, and Latin tunes, and goes by the name Terry Dactyl. She’s currently working on the first draft of a book about the revival funk and soul scene with a special focus on the independent label, Daptone Records. Her book is slated to be published summer 2021 by Jawbone Press.
I met Jessica in 2011 when she hired me as an intern at a local newspaper in the San Francisco East Bay, where we both grew up. As my editor, Jessica sent me all over Contra Costa County to city council meetings, events, and businesses. I credit her with nurturing my first pangs of hunger for storytelling and I still consider her one of my most trusted journalism buds.
We had a great conversation at the end of July about our worth as journalists, navigating the muddy waters of publishing, her advice for writers new to the field, and finding meaning in our work.
What do you tell people when they ask what you do?
I tell them I’m a journalist. It’s probably the most all-encompassing thing. I have worked in a variety of newsrooms and at startups as an editor and content developer. I’ve written bios for executives, bands, and even an escort once. I’m also a freelance culture journalist.
How did you become a journalist?
I was super nosy as a kid, so my options were either be a journalist or a private investigator, but I’m too nice for that. I studied journalism at San Francisco State University. I graduated in 2010 right into the recession and landed a staff editor role at my hometown pub, Embarcadero Media. I tried so hard to leave our small town and kind of ended up right back where I started! But I gained important skills there as an editor and writer.
Jessica’s favorite stories to report:
This piece on boogaloo for NPR's Code Switch
A story for Columbia Journalism Review on the Black Panther Party newspaper
Her manifesto about ska for Billboard
A breaking news piece about #MeToo allegations against a Dave Matthews Band member, who was subsequently kicked out
When did you decide you were ready to be a full-time freelancer?
I feel like that decision was kind of made for me. Media is so fickle and I have not had a lot of job stability in the past four or five years. I’ve always had a freelance practice because there was always a lot of stuff I wanted to write about outside of what my staff jobs covered. Every time I would lose a full-time job, I’d turn to the freelance work as a way to keep myself relevant while I was on the job hunt. I’ve had 7-month stretches where I was freelancing while looking for work. This past year, 2019 to early 2020, I worked at two different startups. The first one was a really bad situation, the second one folded after six months. A lot of jobs have dried up because of COVID, but I’ve gotten a few bylines. I feel really blessed that my time is mostly being taken up by writing my book.
How did you come up with the idea for your book and how did you pitch it to publishers?
Music is such a huge part of my life and always has been. I came to the idea of writing this book because I’ve been following these roots and oldies music subcultures for a long time. I would pitch those stories to various major publications, but they would tell me it’s too niche or that a staff writer would cover it. I felt like I was kind of ahead of the game though, so I decided to do my own thing. Two summers ago, I was at a show and had the aha moment. I put together a proposal for a nonfiction book using development resources I'd found online and through the Binders group on Facebook. Then I pitched to various agents and parted ways with two who didn’t fit my style. In the literary world, major publishers typically only accept proposals from agents and not unsolicited proposals or manuscripts from independent writers. There is a ton of gatekeeping that exists. I thought journalism was messed up.
This past November after talking with some friends, I realized that my book was a little too broad and that I should re-evaluate my angle to focus on one label—Daptone Records—and put the larger scene in context. I went to the library, took every music book off the shelf, and started making a spreadsheet of their publishing houses. I didn't want to find an agent again, so I pitched on my own to a bunch of indie presses. I got some positive feedback and ended up talking to two different presses and went with one in the UK called Jawbone Press.
What’s the money like in book publishing?
The first press was going to offer me an advance of $1,500 and 7 percent royalties on my book. If I sold 10,000 copies, I would get 8 percent royalties. I would probably also have to pay to source photos. My current place offered me an advance of $3,000, which I have to pay back. I get them in installments of $1,000. I also get 12 percent royalties.
I’ve kind of come to terms with the fact that this isn’t going to be a big moneymaker. I think that this is a really difficult thing that a lot of creative women face. I feel like we always have to negotiate writing for the “capital C cause” or for the love of it with what we’re getting financially. I see this book as a labor of love and at this point, my life’s calling. What I hope to get out of it is recognition and great success, and I hope it makes me an authoritative documentarian of the scene. I’ve worked really hard to develop those relationships.
In the freelance world, how do you set your rates and negotiate for more?
A lot of times, the rate-setting is not up to me. When I started in the culture space at alt weeklies and nonprofit media, such as East Bay Express and LA Weekly, most of those are averaging $125 to $150 for digital stories or, in the case of the weeklies, a single page or half page print. I’m like, well I’ve just gotta take this. Over time as I developed relationships with my editors and put together well-reported, clean pieces, I’d ask for $50 or $100 more. I’ve been doing that for seven years at this point. I do feel like I have a little bit of cachet now. I don’t want to get out of bed for less than $250. The last two stories I’ve published have been for a major media organization. They were both $300. I think I should be making more like $500.
But I always have trepidation asking for more, and hemming and hawing over what is the right thing. I am a good reporter, I over-report, and I think I’m a pleasure to work with. I would like to learn how to better negotiate for what my time and energy is worth without losing business or without cutting ties with editors. I think that it’s really important that writers and content creators are fairly compensated. You can’t eat experiences.
Need help editing, creating and developing content, or writing a new bio? Or know someone who does? Hire Jessica.
(Where Jessica gets shit done. And also where she keeps her snacks.)
What does your workspace look like?
I’m a very tidy person, though my work desk has been known to be a bit more messy. My workspace is in my kitchen and is separated by some very groovy beads. Before COVID, I’d work from my desk a lot and then I’d go to the library and coffee shops. But now I can’t really do that, so my workspace is my wooden kitchen table. I recently got a monitor. I don’t get great light in my apartment, but I have a bunch of plants in there and groovy show posters. When I need to stand because I have a bad back, I have this janky ass standing desk that folds down.
What gets you in the mood to write?
Seeing music. It’s been really tough to find inspiration lately because I am so inspired by seeing other creators do their thing. Right now, I feel at such a loss spiritually and communally. There is nothing better than going to a show that takes me the fuck out of my head. In absence of shows, a good deadline, good interviews, and generally if it’s later in the day. I’ve learned over the years that I’m not a morning writer. At the start of COVID, I was on some sort of weird schedule where I’d wake up at 10 a.m., chill, do maintenance, and then I would write from 6 p.m. until 2 a.m. Nighttime fuels me. Good wine fuels me. Also listening to some good records.
(Jessica is a DJ who spins soul, funk, reggae, and Latin tunes. Photo by Mini Kurhan.)
What’s something you want people to know about your field, whether it’s someone just getting into journalism or someone outside the industry?
If you’re just getting into the field, brace yourself. When I was getting into the field, things were messed up. They are going to continue to be messed up. This is not the place for easy, good money. But if you are a committed storyteller, have a drive to share other people’s narratives, and like digging into corruption, then hell yeah, don’t be discouraged by the fact that this is a hard job and getting harder. Also, you’ve got to be super dedicated because COVID fucked it up more. I would suggest diversifying your portfolio. Sure you are an investigative journalist, but maybe you do social media on the side or maybe you write press releases for brands.
And if you are an outsider looking in, subscribe to something. If storytelling is important to you, pay for your local paper or The New York Times, or become a paid subscriber to a writer’s newsletter. Your money does actually go somewhere.
What do you hope people get out of your work?
I hope that they learn about cultures, subcultures, and people who are doing good work to influence things on a broader level. I hope they learn to champion underdogs a bit more. I also hope that specifically when I’m writing about music, that they get turned on to some really dope stuff. Music has impacted my life so amazingly and wholly that if something I wrote gives a reader a new favorite record, then I’ve done my job.
Is there someone you want to see featured next? Nominate her.
Before you go…
Here’s a free coronavirus survival guide (Ten Percent Happier)
Support Black-owned businesses (curated by Zerina Akers)
Study Hall is a valuable newsletter and network for members of the media (h/t Emma Athena)
