Courtney M. McSwain, Writer

Anatomy of a Freelance Writer’s Life: Q&A with Kate Bolick


Photo Courtesy of Kate Bolick

Writer Kate Bolick had me at her Twitter nap reviews. As someone who loves naps, but often feels guilty when I take them, I felt I had a kindred spirit when I first came upon Bolick’s reports of her mastering the art of the power nap on Twitter. I’m hopeful about the future of my own mid-day snoozing when I read tweets from Bolick, like:

“Today’s nap: F; 2hrs; True confession, I’m in a dismal slump and trying to sleep my way out of it. #dailynapreview #editorialtransparency”

“Today’s nap: A+; 30mins; *snuggle*. #dailynapreview”

Of course, napping isn’t the only reason why I admire Bolick and wanted to interview her for my Q&A series. She knows a thing or two about the freelance life and is a successful features writer, essayist and editor whose work has appeared in Elle, The Boston Globe, Domino, The New York Times, Veranda, The Wall Street Journal and Slate. She is also a contributing editor for The Atlantic, where her cover story “All the Single Ladies” about modern day “singlehood” was optioned for a Sony television series. So basically, she’s like my twin!

Bolick was gracious enough to agree to an email interview and tell me about how she has been able to sustain a full-time writing career, create areas of specialty for her writing without being limited and clue me in on the fundamentals of napping efficiency.

CM: How did you come to writing?

KB: Growing up I was always writing stories and poems. In college I decided I wanted to be a poet, and after graduation I got a job at The Atlantic Monthly and eventually became an editor on the magazine’s website; I managed the poetry section and conducted in-depth Q&A interviews with poets and novelists. I loved doing the interviews so much that rather than pursue an MFA in poetry, as I’d planned, I decided to try writing literary criticism. The thing was, I didn’t know how. I’d been a dismal paper-writer as a student, and couldn’t build an argument to save my life. It occurred to me that graduate school could give me the time and space I needed to figure it all out. In 2000, after four years at The Atlantic, I applied to the MFA program in Creative Nonfiction at Columbia, and the MA program in Cultural Reporting & Criticism at New York University. NYU offered me funding, so that’s where I went.

CM: That’s really interesting that you went into cultural reporting and criticism for your graduate degree. Is that close to journalism school? I don’t have a j-school degree myself and often wonder how I can make up the difference, or, if in today’s landscape, it even matters. What do you think?

KB: The CRC program is a specialized concentration within NYU’s journalism institute. Back when I enrolled, I was interested primarily in cultural criticism and essays, not straight-up journalism, so a traditional journalism degree never occurred to me. From what I can tell a degree doesn’t matter at all, and if you don’t get funded by the school (or have rich grandparents or something), it’s probably a waste of money. For me, having the time to get my bearings within the “safety” of academia, rather than out in the marketplace was invaluable.

CM: How did you start freelancing professionally? Why?

KB: In graduate school I thought reviewing books would be a great training ground for writing longer essays. I’d studied history and literature in college, and love to read, so I applied myself to learning how to turn my response to a novel or biography into convincing prose. I also devised an area of “expertise” for myself based on my interests——basically, New York history and women writers——in order to establish credibility. By the time I finished school in 2002 I was reviewing regularly, and over the years I expanded my interests to write features, profiles, travel stories and personal essays for a range of publications.

CM: I actually never thought about writing book reviews as a way of getting practice with longer essay writing. Okay if I steal that idea?

KB: Please do!

CM: You mention setting an “expertise for yourself,” which relates to another question that I have on writing and branding. What are your thoughts on writers building a brand for themselves? Do you think it’s important? Many of your writings focus on issues related to marriage and modern-day “singlehood.” Do you think people consider that to be your writing brand? If so, is that [having a brand] something you like?

KB: I can’t stand all the talk these days about personal “brands,” as if we’re all mini-corporations, so I certainly don’t advocate building one. It’s too limiting. What if you establish yourself as a political journalist but find yourself fascinated by——I don’t know——a big museum exhibit? Too, you risk making yourself a less interesting writer. When I was an editor at a home-lifestyle magazine I preferred assigning stories to freelancers who had a wide-ranging sensibility and a strong voice, rather than those who were straight-up “lifestyle” types.

That said, it’s very useful to pinpoint a few topics that genuinely interest you, and learn all you can about them. It gives your work more authority, and makes it easier for editors to think of you when they have assignments. As for me and “singlehood”: Well, it put me on the map, and because it’s interested me for a long time, and continues to, I don’t mind for now. But I hope I don’t get entombed by the topic.

CM: Have you always been a freelancer or did you work on staff for a publication? If both, which do you prefer and why?

KB: I’ve done both. Making a living as a freelancer in New York is nearly impossible, and from what I can tell it’s more difficult now than ever. After graduate school I wrote freelance full-time for about a year and a half, went insane, and got a staff job. Ever since, I’ve toggled between writing freelance full-time and working full-time as a newspaper and/or magazine editor while continuing to write freelance on the side. I’ve never been a full-time staff writer, which would be pretty dreamy.

As for which I prefer: It’s hard to say! I love freelancing for the freedom, the fact that you have time to do laundry and cook dinner, the weirdly thrilling highs and lows. But the money-panic is beyond dreadful. Full-time jobs are great for the security and stability, obviously, and making new friends at the office, and being exposed to ideas you’d never think to bother with on your own, but they can be incredibly exhausting and draining. I love my current arrangement: Working full-time on a contracted book while writing the occasional article. That said, I really miss chit-chatting with coworkers.

CM: Speaking of balancing full-time and freelance work at the same time, how have you navigated balancing multiple duties and multiple clients? Do you ever have down time?

KB: This is a great question. For many years I basically didn’t have any down time at all. I mean——I don’t even know if I have useful advice for this. I suppose one tip is to create strong, reliable working relationships with your editors, but also be aware of which assignments are most important to you, or have the most value, so when four deadlines suddenly crash down on one day you can be honest with yourself and your editor and prioritize accordingly.

CM: What inspires you to write? Do you ever have inspiration droughts? If so, how do you deal with them?

KB: When I notice something out in the world, or start thinking a lot about some idea that’s new to me, and feel myself getting really excited about it——that’s when I pitch a story. I haven’t had droughts exactly, but starting out it took me forever to learn how to turn ideas I liked into stories a publication would actually want to print. Now I turn everything into a story idea, and have to stop myself from pitching them. For instance, while on vacation recently in Costa Rica, I got to watch a legendary surfboard maker shape a surfboard, and it was all I could do to not contact a travel editor and turn the experience into an article.

CM: I totally do that too! I have ideas that I sometimes want to give to other people just because I think they’d be great stories but I know I don’t have time to write them. Maybe that’s one of those “You know you’re a freelance writer when…” things!

KB: You should give them away on your website!

CM: Good idea! So I absolutely love your nap reviews on Twitter! Why did you start them? What are you hoping to accomplish?

KB: Hah! I LOVE that you are asking about this. Here’s the deal: I love to nap, I have always napped, napping is in my DNA (literally; my father is a huge napper, too). But when I started working full-time on this book and found myself napping every single day, not just on weekends, things started to feel a little out of control. Like, the nap owned me, I didn’t own the nap. I’d konk out for an hour, wake up, and want to murder the poor UPS guy for ringing the door buzzer. I suck at Twitter, so I started The Daily Nap Review as a way to amuse myself by tweeting on my own inane terms, and along the way maybe give my bad habit some much-needed dignity. Instead something else happened! Thanks to people Tweeting back about the merits of the 30-minute nap, I decided to actually try it out for once (instead of being all, “Yeah, yeah, I hear that all the time, but for whatever reason I’m a special snowflake and need a full hour”), and THE 30-MINUTE NAP CHANGED MY LIFE.

CM: When I first started freelancing, I had serious nap guilt. I thought I was being lazy, but I’ve heard from other writers that naps actually help if they are used in the right way. What role do you think naps play for writers? Do you ever have nap guilt? If so, how have you dealt with it?

KB: Now that I’ve mastered the 30-minute nap I have zero guilt. It’s amazing. You set an alarm for 30 minutes, lie down, preferably on a sofa instead of the bed, maybe put on an eye-mask, turn on a fan to drown out noise, and when the alarm goes off a half hour later you spring up genuinely refreshed. I think I’m even sleeping better at night, as my doctor said I might. I haven’t gotten to the point where I solve work problems during the nap, the way I sometimes do during a dream at night, but I’m hopeful.

CM: What have you learned about being a freelancer that you didn’t know when you first started?

KB: Exercising a few times a week is key. Otherwise, all that sitting around makes you feel like a blob. It’s good for the brain, too. I’d exercise every day if I could (sadly, I’m too lazy). I’m also a big fan of the uniform, so you don’t have to think about what you’re putting on in the morning. In the winter I wear a loose denim button down shirt with chest pocket (for my iPhone, so I can type while conducting interviews) and legging-pants; for summer the shirts are sleeveless and the pants cropped. Boom. Dressed.

CM: What’s the dream for Kate Bolick?

KB: Get this: I am actually living my dream. I have always wanted to write a book——and now here I am, doing it. But guess what? Writing a book is terrifying. It’s the most difficult thing I’ve ever done. Whole days pass in a fog of despair. So now my dream is to just finish the book without it being a total disaster. If it ends up going well, I’d like to write more.


Many thanks Kate! You can learn more about Kate Bolick by visiting her website or following her on Twitter.

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