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Curtis Sittenfeld on Choosing Beta Readers, Outlining and Creating Complex Characters

Bestselling author Curtis Sittenfeld (Eligible) explains how her characters keep it “real,” and why plumbing the awkward and uncomfortable can lead to the richest social commentary.

In this extended interview from the October 2018 issue of Writer's Digest, bestselling Eligible author Curtis Sittenfeld explains how her characters keep it “real,” and why plumbing the awkward and uncomfortable can lead to the richest social commentary.

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Ask Curtis Sittenfeld who she writes for, and the answer comes easy: “Other writers, of course!”

If you know Sittenfeld’s work—masterful demonstrations of literary prose coupled with insightful, unblinking inquiry into emotion, identity and the human experience—it’s little surprise she aims to please just the crowd most authors would claim among their harshest critics.

“I think writers [in particular] notice and appreciate what other writers are doing,” Sittenfeld says. “It’s like they can see the machinery, see the scaffolding. So if you can get another writer to suspend disbelief and just read for pleasure or climb into your fictional world, that’s a huge achievement.”

Sittenfeld has a long history of impressing other scribes: Before her senior year of high school she won Seventeen’s 1992 fiction contest and, a few years later, was named one of Glamour’s “Top 10 College Women.” After graduating from Stanford in 1997 with a degree in English, she joined the editorial staff at the newly minted Fast Company. Two years later, she nabbed a coveted spot at the prestigious Iowa Writers’ Workshop where she earned her MFA.

[Don't miss Curtis' keynote at the 2018 Novel Writing Conference this October!]

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In 2005, at 29, she released her debut novel, Prep, a boarding-school set coming-of-age tale that quickly became a New York Times bestseller. Five other fiction titles—many of which also became bestsellers, were optioned for film and television, and have been translated into more than 30 languages—were released in regular succession. Prep was followed by The Man of My Dreams, a story that follows a young woman’s trials and tribulations in life and love over a decade-and-a-half; American Wife, a fictional account of a First Lady loosely inspired by the life of Laura Bush; Sisterland, about psychic twin sisters; and Eligible, a modern, Midwest-based retelling of Jane Austen’s Pride and Prejudice.

While writing novels, she’s also published numerous short stories and essays in such esteemed markets as The New York Times, The Atlantic, Slate, The Washington Post, Time, Vanity Fair, Esquire, The New Yorker and more. Several of her stories that appeared in The New Yorker were included in her first collection, You Think It, I’ll Say It, published in April.

Sittenfeld took a break from book promotion to talk with WD about her process, writing awkward confrontations and crafting unlikeable-yet-empathetic characters.

You’ve noted that “so much in life that’s a little bit awkward … is just ideas for fiction.” And that’s something we see a lot in your latest book, You Think It, I’ll Say It, where the characters often find themselves in intensely cringeworthy situations. How do those sorts of interactions inspire your writing?

I can’t imagine writing scenes where the characters are not emotionally invested, even if it’s a negative emotion. I think that when people are having awkward feelings, there’s potentially a lot of complicated things going on. That can be interesting. And if you start to unpack why you felt awkward in a certain moment … it’s not always multilayered, but it certainly can be.

You do a skillful job creating characters who are “real” and complex, but are also empathetic (if not necessarily likeable). What’s the key to walking that line?

I think that saying who’s likable and who isn’t is very subjective. And so I actually don’t really think I can control that. I guess it’s more like I could create pretty inoffensive characters who, to me, would be very boring—but [that] most readers would not find objectionable. That’s not really my goal. I’m so lucky I get to write fiction, because the last thing I would want to do is bore myself while writing it. [Although] I would never think to myself, “Does this dialogue or gesture make a character likable or unlikable?” I would think in terms of, you know, Is this character transgressing in a way that I mean for her to transgress? Or, you know, Is she being fair to other characters? Or, Is she being mean to other characters? So I wouldn’t really think about her likability in terms of the way the reader receives her, but I would within the ecosystem of the story.

That makes sense. Like, are they brimming with malice toward other characters?

Yeah. And if they do have malice, is it serving the story? ’Cause if it is, then that would be left in. [Laughs] But I don’t think that I would include malice for the sake of malice. I would include it because it made the story interesting. Or revealed something about the characters or advanced the plot. But it’s not like my overarching goal is to explore the nastiest side of humanity.

Your latest book is of short fiction, but you’re known for your novels. How do you decide whether a piece can sustain a full novel, versus being a better fit for the short form?

For something to be a novel, I have to get an idea that seems like it's this huge thing that I can approach in like 17 different ways. And if someone asks me why I found it interesting, I could spend four hours explaining why, because it feels infinitely interesting. Whereas a short story feels more contained. It still feels intriguing, but [more] like this sort of fleeting or brief thing, instead of feeling infinite. It’s more like conceiving of a moment instead of conceiving of a massive topic.

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You have written everything from personality profiles—including of Michelle Obama Barbara Walters—to short fiction and novels. How does your writing process for short stories differ from longer formed pieces?

I have a lot of respect for a lot of journalists. I think that sometimes the general reader doesn't always understand the distinction between reported journalism and personal writing or essays. When I graduated from college in 1997, I was an intern at the Charlotte Observer in North Carolina, a general assignment reporter. Then I went to work as a staff writer for [a publication] in Boston. So I have some journalistic experience, but this is now more than 20 years ago. And I feel as if some of my journalistic muscles have atrophied. I could write a reported piece but it used to be that I did it once a year, and now I do it maybe once every three or four years. I sort of feel like I went down the fiction path, not down the nonfiction path. I mean, there is a difference. And fiction is more and more accessible to me and nonfiction is less and less accessible to me.

There's also a time after graduate school, before my novel Prep came out, that I wrote a fair number of sort of semi-reported essays, or sometimes I'd write things for women's magazines or for Seventeen magazine. Some of it was reported, some of it was essays. But now—I can't tell how much of this is artistic preciousness on my part and how much is sort of legitimate—but there are times when I feel like it's harder and harder for me to write nonfiction the older I get, unless I care about it. There’s some idea that around publication time, it's ideal for a writer to write, you know, a few personal essays to promote the book. But I feel like at this point, you know, if you said to me, "You could write an essay about your relationship with your hair,” or something I don't really have very strong feelings about. I think I'd be capable of it, but it would not be very enjoyable just to write something for the sake of writing. Whereas, if you ask me to write about nonfiction that I'm emotionally invested in, I think I can still do that. And again, it all depends. Like I think it uses slightly different but overlapping parts of the brain.

I actually feel that way also about writing for TV, which I've done a tiny bit. I’ve written a little bit of, you know, sort-of-screenplays that have not made it to a screen. And I almost feel as if I could rewire my brain. But I personally find it difficult to switch back and forth between formats, you know, between a screenplay and fiction. Fiction feels much more natural to me.

You’ll often use your two sisters as your beta/early readers, because they’re “sort of out of the loop with the publishing world.” I think most people would assume you’d [figuratively speaking] want the opposite—readers who are keyed in to “what sells.” Why is it important to have readers like your sisters? How does one find a good beta/early reader?

Well, my sisters not really my earliest readers. My earliest readers are other writers. If I write a story and I'm wondering if it's finished or not, I would show it to a few of them. I probably have a roster of maybe 10 writers total, and I might show any given work to like five of them depending on the subject of the story, depending on what's going on in my friends’ lives, how busy they are. And then if the story is [at the stage where] my editor is looking at it but maybe there's still time to change things, that's when I would have my sisters read it.

I mean, sometimes, I actually will have [one of my sisters] do almost like general quality control or humiliation control. [Laughs.] Where if I write an essay or personal I might share it with her—not really to say, "What do you think of these sentences?" But to ask, "Am I revealing too much about myself?" Or, "Is this in vain?" So it’s not exactly writerly feedback that I'm looking for.

So, sort of asking her to look for general appeal, overall?

It's usually more specific than that. I mean it really is kind of like saying like, "Do I sound like an idiot in this? [Laughs.] The fact is, especially because there's so many online venues, at this point I could get something published that's not really in my best interest. And sometimes it takes someone like a sister to be really blunt and to say like, "You know, you sound like a jackass in this essay, and you shouldn't publish this."

That makes sense. Do you have tips for finding good beta readers then?

I think, I think that taking a writing class in a place where you live or you know, if you can afford it, going to a writing conference like Sewanee [Writers’ Conference] or the Iowa Summer Writing Festival in Iowa City in the summer; or, if you take an extension school class at a local university or writing center. I mean … you won't necessarily find your writing soulmate. But if there’s 14 people in the class, maybe one or two of them will be on the same wavelength that you are.

2nd Draft critique and editing services can help you perfect your manuscript.

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You’ve talked before about your creative process, saying sometimes an organizational issue is more to blame for feeling stuck than a content problem. How can other writers recognize this occurring in their own work and go about fixing the issue?

It’s funny, because I have a writer friend named Sheena, and she and I talk about this all the time. A phrase that we use a lot with each other is “paper management.” I think sometimes a writer, including me, could feel as if maybe they’ve written 60 percent of a novel. But it’s not the first 60 percent—it’s sort of out of order. And then maybe 30 percent of it doesn’t exist and then 10 percent of it is really messy. And [that makes the] whole document feel kind of intimidating and I don’t know where I should enter it or how to tame it. And so something Sheena and I talk about [that helps] is to print out the whole thing, and within that one stack of paper, take the sections that are basically finished and put paper clips around those parts. And then take the sections that are messy and put them in blue folders [or whatever]. And then take the stacks that don’t exist and put manila folders as placeholders for them. Then you think to yourself ahead of time, OK, I’m gonna go through the blue folders first on these days. And then I’m gonna go to the manila folder.

I find that, in general, if I plan ahead what I’m going to do with my own writing or even when I’m going to write, it goes more smoothly. If you sit down and you don’t know what your plan of attack is, you can feel immobilized and then just decide to check Twitter. And then your day goes down the toilet. I think that there’s this element of feeling, from an organizational perspective, as if you’re in control of your manuscript and that can actually allow your creativity to proceed.

You have a very different process than most writers I’ve interviewed. Are you familiar with the “plotting versus pantsing” debate?

Ha! Oh no, oh no, is that like flying by the seat of your pants? Oh, God, I don’t know if I’ve heard of that, but I can tell you right now: I do not believe in pantsing.

You do seem like more of a plotter, though actually I can maybe see both.

Yeah. I do outlines and then I change the outline as I go along. I would never tell someone else how to write her novel if asked, nor [give] unsolicited advice, like, “This is how everybody should do it.” But I do think as a reader—I bet if you gave me 10 novels and said, “Guess which writer outlined and which didn’t,” I don’t think I’d have a 100 percent success rate, but I feel like I could probably guess more often than not who did and who didn’t.

I think I believe more in pantsing for a short story than for a novel. [In a novel], 300 or 400 pages is a lot of material to manage. [To me] it’s almost like, you can get through a day without planning your day. But you can’t get through a year without planning your year.

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You have an MFA from the Iowa Writers’ Workshop, which is well-known for its literary prestige. I’m sure it’s so difficult to boil down, but what favorite piece of advice did you learn there?

I started at the workshop on my 24th birthday. And I actually, naively, thought to myself [at the time], I won’t learn that much about writing, but I’ll have time to write. And then I actually learned a tremendous amount about writing. The No. 1 thing that I learned, and it was life-changing for me, was from Ethan Canin, who was my professor and my advisor. The way that he talked about structure made me think about structure, and it gave me control over my own writing. And I think it’s usually structure that determines the success or failure of any piece of writing, whether it’s fiction or nonfiction.

You once quoted an editor who said, “People think publishing is a business, but it’s a casino.” How do you take that statement, as an author? In your experience, have you found that to truly be the case?

It’s funny because I think a lot of people, including published writers, sometimes think the system is sort of rigged. And to some extent, the system is rigged. It’s undeniable that if a publisher pays a large amount for a book, it means that they will get behind it, in terms of promoting it. And [even] if there are limited resources, they will use those resources. But that doesn’t mean the book will be a bestseller. A publisher can’t really manufacture a bestseller out of thin air—because if they could, they would do it every time. Every editor has had their heart broken many times believing in a book that just doesn’t get very much attention or traction. And the inverse is true, where a book doesn’t necessarily have much institutional support but then does end up getting attention and finding readers. There are things that a writer can contribute to the overall publication process, but a writer cannot control how many books sell. I don’t know if that’s more disappointing or liberating for writers to hear.

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Write Smart, Write Happy: How to Become a More Productive, Resilient, and Successful Writer

Many of our readers juggle writing on top of another profession, and finding time to write is a challenge. What is your advice for finding and guarding that writing time?

Decide ahead of time when you’ll write. Maybe plan out a week or two weeks or a month at a time. Write it into your calendar, whether it’s an hour every day or half an hour once a week. Then, treat it like a commitment with another person that you like and are lucky to spend time with. Don’t treat it like drinks with your friend that you secretly are going to bail on [Laughs]. And during your writing time, just sit there—you don’t have to write, but just sit there and don’t get online. If you think of things that you have to do—whether it’s change the laundry, schedule a doctor’s appointment, whatever—write it on a little Post-It next to you. You might have to sit there like four times before you really do write, but you just have to train yourself to attack this time. A journalistic trick is putting the letters “TK” as a placeholder. Let’s say you want to find a song from 1976. Put “1976 song TK,” in your work-in-progress, look it up later, and therefore avoid going down that internet rabbit hole [during your writing time].

Often when I give writing advice, I think, Oh, God, Curtis, this is what you should do [Laughs].

Your first novel, Prep, became a NYT bestseller, which tends to put additional pressure on subsequent books. How did you handle that pressure? And looking back, knowing so many of your books have become bestsellers, what would you tell your younger self?

I think the pressure is hard to quantify. You know, like what does that mean exactly? Does that mean you hope that your other books sell a certain number of copies? Do you hope they get a certain flavor of review? It’s hard to say. I think that almost any advice I would’ve tried to give my younger self, I’m probably much likelier to believe just because of my own experiences. And publishing has changed. My first book came out in 2005. Digital readers didn’t exist for my first three books, and it was like 0 percent digital sales. And then when Sisterland came out in 2013, it was close to 80 percent digital sales. It was this huge change.

You and I were just discussing what the writer can and can’t control. Really, the only thing I can control is the writing, and so I think I should try to write books that I feel very emotionally invested in, and should work hard to make them the best that I can make them. And beyond that, you know, I should try to be polite and pleasant to work with [Laughs]. I guess if I were to give advice to my younger self, it would be that your own sense of success will wax and wane. The work is the constant. Stay focused on the writing and remember why you became a writer—which is just that you like to write and you like to read.

What’s up next for you? I’ve heard that an adaptation of You Think It, I’ll Say It is slated to become a 10-episode series for Apple Worldwide Video, starring Kristen Wiig. Do you have plans to play any role in the production of that?

Reese Witherspoon’s company, Hello Sunshine, is [producing it], and Reese and Kristen Wiig and a writer named Colleen McGuinness are all working together and developing it. I’m in contact with Colleen, and sometimes she bounces ideas off me. I would have a title with the show. But I would not work in California and it would not be a full-time job. I’m also writing a novel about Hillary Rodham, [around when she fell] in love with Bill Clinton. In real life, she declined his marriage proposal a few times and then eventually accepted. In my version, it’s, What if she declined his marriage proposals and then went on her own way? It’s occupying my brain, so I guess that’s a good sign. WD

Read more and discover our annual Agent Roundup in the October 2018 issue Writer’s Digest. And subscribe to get WD all year long.

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