Jessica Winter Skewers the Modern Workplace

I’ve been reading Jessica Winter’s writing practically since she started publishing. Back in the late ’90s and early aughts, we were both editing and writing at The Village Voice. She produced a seemingly endless stream of reviews and features — on film and books, mostly — that were reliably brilliant, whether it was a meditation on Russell Crowe or a look at a forgotten literary oddity of the 1950s (Nigel Dennis’s Cards of Identity). Her surname was almost too perfect, given the wintry clarity of her sentences. Elegant braininess! What couldn’t she write?

Jessica eventually did editorial stints at O and Time, while also contributing to a variety of publications, including Bookforum. Now an editor at Slate, where she frequently writes on politics and culture, Jessica has published her debut novel, Break in Case of Emergency, which is at once marvelously inventive and aimed straight for the heart. Just read the first few pages, and you’ll see that rare first-time fiction writer who knows exactly what she’s doing, one keenly observed sentence after another.

Jen is trying to find her footing in her early 30s, in the belly of the beast (aka New York City) — navigating work and art, longing to start a family, After a stint of unemployment, she finds a job at LIFt, a purportedly women-centric charitable foundation-cum-vanity project run by the gloriously named Leora Infinitas — a wholly original creation that nevertheless might remind readers of, say, Gwyneth Paltrow crossed with Arianna Huffington. Jen’s title is Communications Manager and Co-Director, Special Projects, a title she shares with a colleague: “Neither of them could have always stated with certainty which projects they were intended to manage, officiate, or codirect, or which qualities made any particular project special.”

Break in Case of Emergency is one special project — a precise mix of the absurd and the heartfelt. I caught up with Jessica via Gchat recently, a fun exchange in which, inexplicably, chunks of some of my questions appeared with lines struck through them. It occurred to me later that this was a detail that could have appeared in her novel, which among many things is a lovely contribution to the field of workplace literature.

Ed Park: We were colleagues long ago, working at the same newspaper, The Village Voice, often in the happy situation of editing each other’s pieces. If you don’t mind my saying, I’ve been a fan of your journalism basically since your first film reviews started appearing. “Who is this Jessica Winter?” I wondered, before I put a name to a face. There’s a precision in the thinking and a hotness to the prose — perhaps one demands the other — that I’ve always found exciting. Now you’ve written a novel, Break in Case of Emergency, which has those same virtues, on a bigger scale — and a magical something else as well. I’d love to know about the origins of the book, and any challenges or pleasures you discovered in turning your hand to fiction.

Jessica Winter: Ed, you are so kind! I remember that on my first day at the Voice, someone said to me, almost as if they were letting me in on a delicious secret, that “Ed Park is the funniest, smartest person here.” And I thought, well, I need to investigate this Ed Park fellow immediately. And they were right!

Park: That was actually me saying it, in disguise.

Winter: I was in my mid-thirties before it ever seriously occurred to me to write fiction. One of the nice things that happens when you’ve been writing and publishing nonfiction for a while is that, inevitably, these lovely people known as agents start asking you out for lunch to talk over ideas for books. That’s the expectation for your next step: “You’ve written all these articles; now you write a book!” I was always halfway decent at coming up with ideas for articles but really, really terrible at coming up with ideas for books — the two skills don’t necessarily have much to do with each other. A piece of advice that I kept getting was: “Whatever book you write, make sure it’s the kind of book you yourself would read and enjoy. You’re going to live with this book for years, so you have to be the ideal audience for it.” The truth is, whenever I have free time to devour books, those books are novels. So that’s how the seed got planted: “Why have I never tried to write one of these things that I love reading so much?”

I had two overlapping ideas for a novel rattling around in my head for a long time. One was a parody of a celebrity charitable foundation, specifically one that located itself inside the feminist-empowerment industrial complex. It felt like endlessly rich terrain, and I hadn’t seen it explored in a satisfying way elsewhere. The other idea was to explore the experience of infertility and early pregnancy in a workplace, specifically one that wasn’t especially sympathetic to people having bodies and lives outside of the office, and one where a kind of blind fealty to “openness” and “authenticity” would mean that an employee with reproductive health issues — or any health issues, really — wouldn’t necessarily be granted space or privacy.

At first I would just jot down little musings and vignettes and snippets of dialogue in spare moments and send them to myself in Gmail. It was the most haphazard way of starting a book.

Park: I do that, too — email myself musings, character ideas, particularly inspired puns. And then they’ll pile up and get pushed further down the inbox, so mostly I don’t see them till I’m searching for something else entirely and then that message pops up.

Winter: Yes! I didn’t even really have a decent search-word or folder system worked out. It’s altogether possible that I have a scene or line of dialogue or half-baked theme buried in Gmail somewhere that I sent to myself and forgot about.

But gradually all those little scraps started to cohere, and I was devoting more and more time to making them come together, and the whole experience became addictive. When I’m writing a reported piece or an essay, I tend to love doing the research but hate the writing part, and I’ll do most anything to avoid it or procrastinate. But with this, I found myself itching to get back to it all the time, because the writing part of it was pleasurable in a way that I’d never really experienced before — maybe because it was such a new experience of writing.

Park: Break in Case of Emergency is so deftly way-we-live-now, and I do see that as the engine of the story. But what knocked me out, particularly at the beginning, was the sheer joy of the prose. Your articles can be very funny, but I loved the humor here — the sheer invention on display. Obviously we get into deep emotional territory as the book goes on, but I felt that the book comes out of the gate with this heightened take on reality, the sort of inspired satire that I love. The humor is situational but also resides on the language level — in the naming of things, and then going where the name takes you.

Winter: Well, we should say that BICOE is deeply, openly indebted to two office satires: one is Sam Lipsyte’s The Ask, and the other is your own Personal Days. If the reader of BICOE is a fan of either of these books, she will find Easter-egg homages to both books in mine. One of the many things I loved about Personal Days was how you captured office lingo, both in terms of bureaucracy and the kinds of excruciating formal emails you have to write to your boss at times, but also in terms of how office lingo can be a glue that helps colleagues bond with each other. Close colleagues can develop inside jokes and wordplay that becomes like the language of twins, and the way you translated that language and that intimacy for your reader was magical and hilarious and eventually quite moving. That pure delight in language is one of the ways office-mates keep each other going, and I loved that Personal Days celebrated that at the same time that it portrayed cubicle life as often bleak and existentially gnawing.

Park: Jen’s work situation is hilarious and cringe-inducing, but we also understand why Jen is there — coming off a spell of unemployment — and that a big part of her “real” self has been denied for years. Jen’s a talented artist, but lacks the ambition that her friend Pam has. The title of the novel, Break in Case of Emergency, is also the name of the central art installation in the book, which you bring vividly to life. Were Jen and Pam artists from the beginning, in terms of your conception of the story? And though you wrote extensively on film — a visual medium! — early in your career, I wonder how being married to an artist [the graphic designer and photographer Adrian Kinloch] might have shaped your thinking and writing around the subject.

Winter: Yes, I saw Jen and Pam as artists from the start. One of the things that interested me about Jen is that she felt caught between two designs for how to live, each of which she sees exemplified in her two best friends, whom she idealizes. Meg appears to Jen as a perfect straight-world figure, with the beautiful family and the worthy job. And Pam appears to Jen as a perfect rejection of that world, with her crazy installations and her starving-artist boyfriend and her threadbare apartment-slash-gallery space and her apparent lack of interest in money or marriage or having children or any number of other conventional expectations. So Jen does lack Pam’s ambition, but I think her bigger problem is that she lacks Pam’s or Meg’s sense of self, their sense of purpose and identity.

If you’re going to write a book that has photography and graphic design and art in it, I highly recommend being married to a photographer and graphic designer with a fine arts degree. Adrian helped me hone a lot of the passages where we see Jen or Pam at work in the studio, and his final-year project at art college in England was inspiration for some of Pam’s work. An early reader of the book read the passages about Pam’s senior thesis show and said, “No undergrad art department would ever let a student get away with this” and I said, “Oh, I can think of one!”

Park: The first two letters of the name aside, how much of your own experience of New York City have you mapped onto Jen? Would you ever consider writing a novel set somewhere else?

Winter: It took me an embarrassingly long time, and I mean years, before I figured out that many, many people in my industry and related and overlapping industries in New York City — media, book publishing, nonprofit work — don’t live on what they make from those jobs; a disproportionate number of them have family money, a trust fund, an aunt who bought them an apartment, or a spouse in a higher-paying field. If Jen and I have some traits in common — and we do — one was a long-lasting naïveté about how a lot of bills really get paid in New York City, and a general sense at that age of being completely out of our depths when it came to money and how to relate to it and talk about it. As for setting, my next novel takes place in a different city, albeit one that I’ve also lived in and know very well, so I’m probably taking the “write what you know” cliché a little too far at this point.

Park: I’m an old man now —

Winter: And I’m an old woman!

Park: — but I can remember that feeling of figuring it out. Maybe it happens in every city, but New York is the extreme example. And this reminds me that we’re both originally from Buffalo — same state, but as far away as you can get from New York City, pretty much. It plays into my next novel a little.

Winter: Mine, too! And of course you edited Buffalo Noir, which is a brilliant compendium of the city’s seamiest nooks and crannies. People from Buffalo tend to feel a little sheepish about their town, or a lot sheepish, because people not from Buffalo think of snow 10 months a year and four Super Bowl losses. Did you see the OJ documentary?

Park: I saw the first part on TV and was stunned. I’m ancient enough to remember OJ playing for the Bills — why am I talking about my age so much? — and having a poster of him on my wall.

Winter: It’s an astonishing, brilliant documentary. At one point one of Simpson’s former Bills teammates likens Buffalo to Siberia, and the film basically takes him at his word. I guess I can understand why a Californian would feel that way. But Buffalo is historically and architecturally fascinating — there’s so much to mine. And the summers are so nice! I wonder if part of the problem is just the name. The city as lumbering, hirsute beast.

Park: But it’s also mysterious, Jessica — because nobody knows how it got the name! Speaking of names, Jen and Meg and Pam have plain, minimal monikers, but nearly everyone else in BICOE has something sparklingly weird or fabulous to their names, Leora Infinitas being the apotheosis here. It reminded me of Perpetua in Bridget Jones’s Diary — a minor character, I think, but the name will never be forgotten. Pynchon’s names also come to mind. Maybe I can just ask: Where did that come from? Was it like John Lennon being delivered the name “The Beatles — with an a” via a flaming pie or whatever?

Winter: I honestly don’t remember how I came up with it. And I don’t know what came first: LEORA INFINITAS FOUNDATION or its anagram, ADROIT FELON IS IN A FOUNTAIN. But I do remember wanting very badly for her to sound like a character from Infinite Jest, which is one of my all-time favorite novels. That was my starting point — something that could aspire to be even in the same zip code as a name like Avril Incandenza, née Mondragon.

Coming up with names for secondary characters is so fun that it can be a form of procrastination…

I said earlier that I didn’t procrastinate much on this book, but I think that coming up with names for secondary characters is so fun that it can be a form of procrastination or avoidance — you know you have a really difficult transition or structural change to make, so you just keep coming up with silly names for characters who don’t exist yet.

I think I gave Jen and Jim and Meg and Pam relatively simple, generic names — my given name, too, is quite generic — because, on an intuitive level, I wanted as much as possible for the reader to assess them through their words and actions and through Jen’s own skewed perception of them. You might notice that there’s little or no physical description of them. There’s a passage in which Jen notices that Pam has lost a lot of weight that I agonized over and kept deleting and restoring, because even though the passage was important and necessary, I didn’t even want to disclose to the reader that Pam was thin. I kept it in, but overall I really wanted to leave it up to the reader to decide what they looked like, and I suppose having a common three-letter name helped keep that space blank. This is another place where Personal Days is an influence, I think. This is a spoiler, but your final passage, when your narrator reveals his ethnic background, creates a heart-flutter of a moment that has always stuck with me, both on an emotional and a technical level.

Park: I’m glad you liked it — it was unplanned and then very planned, in the moment of writing.

To give a character a name like Leora Infinitas is to announce something about the novel’s world — to announce its fictive nature, even though of course there are unusual names floating around IRL all the time. And then — to take us to the end — you have a great last line that I think can quote here without elaborating on the context: “I am ready to destroy my life.” It knocked me out. What am I saying? Maybe just that many of my favorite books do this — they are authored into being, shaped out of scraps of the real world and the lived life but quite definitely “signed” by the writer, and then, in the end, that world between the covers must cease to be.

Winter: I wrote that line first: “I am ready to destroy my life.” I knew from the very beginning that that was the end of this book, even if I didn’t entirely know how I was going to get there. And then I wrote the first scene of BICOE. I did the exact same thing with the book I’m writing now: I wrote the last scene — the last line — first, and then the opening scene. There’s something about having those bookends in place from the start that makes me feel safe and contained.

I wanted to ask you a question, Ed. When you are writing and you get stuck, do you ever dip into books that you really love to get unstuck? Or is that too scary, like “Ugh, they are so good, I give up!” I ask because I was surprised to find myself doing this in writing BICOE and it really helped me as opposed to being discouraging. I read James Salter’s Light Years while I was revising, and on one level it was completely terrifying, but on the other it left me with this very practical, can-do kind of feeling, like, “Welp, off to Salter-ize all my sentences!”

Rachel Kushner’s The Flamethrowers had a similar effect. I was totally thrown about how to do a scene between Pam and Jen that I knew I needed, and I read the first 30 pages of The Flamethrowers and thought, “I will never be able to write like this; however, I now feel ready to tackle this scene.” I’m curious about how you relate to other books when you are deep into your own novels and stories.

Park: Ha! That is a useful verb: to Salterize. For me it’s generally Portisizing or Wodehousing (to the extent that’s even possible). I’ve definitely had that feeling of “Oh I give up!,” but generally the books I go to are old standbys — it’s not so much that I’ll try to imitate, but maybe the spirit of that book will flow through me. Anthony Powell’s Afternoon Men is another inspirational text.

Winter: I live in futile hope of ever Wodehousing anything. Maybe in a WhatsApp someday. Wodehouse would have been so adept with bitmoji.

Park: The other thing I’ll do is read something that has nothing to do with what I’m writing — something “minor,” something not even remotely literature. Yesterday I leafed through a book of chess openings, written with a lot of zest. I’ve also been rummaging through UFO literature, thanks to a friend who collects it. I love reading transcripts, people talking about what they saw or what they thought they saw. Anyway, I’m going to go do some Winterizing now.

Winter: Your kids are both really into chess, right?

Park: Yes, they like chess. They trounce me.

Winter: I read mostly board books to my daughter, who’s not yet 2, and one of them is this kind of shockingly retrogressive Mother Goose book that we inherited from somewhere-or-other that completely freaks me out and has already wormed its way into my next book. I wrote a whole scene around it. But now I have to go Park-ify that passage, come to think of it.