7 For Seven: 7 Questions For ... Ilana Kaplan

"[Art] doesn't have to be serious. It can just exist. It can be fun. It can have a purpose without intention."

Ilana and her cats, Pumpkin and Bug, whom have learned to levitate

Every second and fourth Friday of the month, Brady Gerber’s “7 For Seven” interviews writers talking about writing. This week’s guest is Ilana Kaplan. Ilana is a freelance music and culture writer/editor who lives in Brooklyn. She was a weekend writer for Rolling Stone, a contributing editor at PAPER Magazine, a news editor at Digiday, and a staff culture writer at The Independent. She has written for The New York Times, NPR, GQ, Billboard, Vanity Fair, and more. And Ilana wants you to check out … her recent New York Times interview with Alicia Silverstone, and her Vulture interview with Phoebe Bridgers (which just ran yesterday!). Read this interview on your browser.

Twitter: @lanikaps

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Tell us: What (all) do you do?

I currently edit marketing content at Dotdash by day, and at night I write freelance pitches and articles I've pitched and been commissioned. Truthfully, when I started out, I couldn't afford to take an editorial job. After college, I ended up taking jobs in marketing and social media because I was able to survive on it. But every night, I'd work on freelance writing with the hope I'd crossover into a full-time editorial job. I did, but it took time. At 27 or 28, I got my first full-time editorial job. I now can freelance while having a steady income, which I've found is nice. I think the industry has become a bit more complex the past few months, but I do think for young and established writers it's just important to be open to things knowing that your bills come first. Take a job that might not necessarily be the "dream" one (I think it's debatable dream jobs exist at this point) but allows you the freedom to create what you want on the side.

Walk us through a typical day.

At my day job, I commission experts to write on a variety of subjects while intermittently editing a handful of roundups a day and coming up with additional ideas and going to meetings. When it comes to freelancing, I generally write topline notes in my Notes app and drafts folder about subjects and where it might be a good fit. I usually try to build out at least one pitch email a day (obviously this doesn't always happen). If I have a few assignments on deck, that takes priority and I don't pitch that week, so I end up transcribing interviews or writing at night and on weekends.

Describe more about how you work; how do you do what you do?

Sometimes I don't even know. I just know I will always get whatever is on my plate done. I think I have always been someone who hustles and will find a way. I will Google or Twitter search to the end of the earth for a contact -- doing the work I think is important because it helps you find out what an editor covers. I've always been persistent, which I think has worked out for me sometimes, and I'm sure in other cases it might be an annoying quality when it comes down to it. But when you freelance write, it's easy to fall into a sea of emails. I've always tried to do what I do with a lot of respect and kindness for the people I work with (and want to work with).

What’s your trick for when you’re feeling stuck?

To be honest, either taking a shower, watching a TV show, or going on a walk. Sometimes, even though I hate to admit it to myself, stepping away is the only way I can be creative again.

List some of your notable influences, past and present: writers, books, works of art, medium-comfort-level socks, anything and anyone that has inspired you.

Rob Sheffield and his book Love Is a Mix Tape is the reason I became a music journalist and in a lot of weird ways became a domino effect on me starting my career. It's one of the best books on rock and a stunning, heartbreaking memoir about loss. Other books I've loved are Ann Powers' Good Booty: Love and Sex, Black and White, Body and Soul in American Music, Lizzy Goodman's Meet Me In The Bathroom, Jessica Simpson's Open Book (yes, it's juicy, but it also reveals the dark inner workings of the pop industrial complex in the late 90s). To be honest I love a good celebrity/artist memoir. I get inspired by anything nostalgic. Most of the time I can probably be found re-watching teen soaps (i.e. The O.C., Dawson's Creek, Buffy The Vampire Slayer). Sometimes it'll even spur an idea, but it also keeps my mind fresh.

In general, some of my favorite writers to read and learn from are Ann Powers (if you haven't read her piece on Lana Del Rey's 'Norman Fucking Rockwell' you should), Maria Sherman (her investigation on the dark side of K-Pop), Craig Jenkins (his intimate interview with Mac Miller still sits with me), Brittany Spanos (her cover story on Janelle Monae was a masterclass in making a subject feel comfortable and getting them to open up), Suzy Exposito (her cover story on Bad Bunny really delved into the creative psyche of the Latin superstar). Amanda Petrusich is also one of my favorite writers and the best article I read recently was her exploration of how K-Pop fans were responsible for hijacking hashtags and creating a political revolution.


Ilana is full of wisdom, right? I also love Love Is a Mix Tape. This interview is possible because of subscribers - thank you for following! Other ways you can support this newsletter: Tip for coffee (so I have fuel to edit everything) and share this dang thing. But the most helpful thing you can do is:

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Advice time: What’s a piece of wisdom that you wish you first heard when you were starting out?

Just because you're doing a writing-adjacent job (i.e. social media, copywriting, marketing content) doesn't mean you've sold out or aren't a writer. You will always be a writer. Paying your bills is most important, but it doesn't mean you stop pursuing your passion/writing in your free time.

“Art”: What the heck is it?

I think it's any form of expression that captures human emotion, vulnerability, love, loss, etc. I also think that it doesn't have to be serious. It can just exist. It can be fun. It can have a purpose without intention.

BONUS: Cats or dogs?

Love them both, but personally, cats - I have two -- one named Pumpkin and one named Bug.

Photo credit: Ilana Kaplan


This is one of two monthly interviews with writers talking about writing, from Brady Gerber’s “7 For Seven.” All cartoons by Brady Gerber. Sign up for the newsletter here.