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The New Yorker’s Susan Orlean on the magic and mystery of writing

Writer Susan Orlean explains the magical process of finding a story. (Video: Lillian Cunningham, Jayne Orenstein, Randolph Smith and Julio Negron/The Washington Post)
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There's hardly a pocket of the media cosmos with more literary journalism stars than The New Yorker, and Susan Orlean has been one of its bright fixtures. She joined the magazine more than two decades ago, writing stories about a gospel group traveling graveled roads through the South, a real estate broker who has nightmares her clients will leave her, a high-school basketball phenom growing up in the South Bronx.

In the meantime she has also written several nonfiction books, including The Orchid Thief, whose tale of Floridians illegally scouring swamps for rare flowers inspired the film "Adaptation." Orlean joins the On Leadership interview series to reflect on her career, the craft of writing and the publishing industry. The conversation has been lightly edited for length and clarity.

Want to listen to the conversation instead? It's the new episode of our podcast, On Leadership: A conversation with Susan Orlean.

Q. What do you think has been a key to your career success?

A. I really love what I do, and I believe in what I do. There’s a mission that I’ve always felt in my work, which is to bring people to learn about the world. Having a purpose has made me look at my professional life as serving that purpose, rather than the other way around.

It’s always been very natural to talk to the person on the street, to turn the corner that leads to who knows where. Then I come back filled with this excitement of wanting to take people by the sleeve and say, “Come here! You’re not going to believe how interesting this is!” Even as a kid, I felt that. It’s curiosity, coupled with the desire to encourage other people to experience that curiosity.

Q. Have the type of things that pique your interest changed?

A. There have been some constants: subcultures, the unexplored familiar, things that you see every day but you’ve never really thought about, people whose lives are not like mine. I have to say, I’ve not been that interested in my socioeconomic group. I’m much more interested in exploring people and places that are not exactly like my life.

Has it evolved? I’d like to think what has evolved is my ability to explore it. But that sense of what is interesting has been fairly constant.

Q. Do you think your writing and reporting has necessarily gotten better with time?

A. I think the biggest thing that has improved is my confidence. With experience, you develop the confidence in your voice as a writer and even in your ability to say to a reader: “Trust me. Come into this story even if you don’t initially think it’s of interest to you. Believe me.” That’s something you only develop with experience under your belt, because it is a matter of believing you can show why something is interesting.

Q. If you look at work you did much earlier in your career, what are some of the ways that lack of confidence would show itself?

A. The real evidence of confidence is writing more simply and in a plainer way. It’s when, as a writer, I’m not defending my choice of subject. I’m not constantly doubling down on why you should read my story.

I’m not sure that I could point to word choice or something so specific as that. But I now believe that I can state my case without providing all sorts of defense for it, and that the reader will follow me.

Q. Does part of that come just from knowing, the more you’ve published books and given talks, that there are in fact people who read you and care about what you write?

A. Definitely. If you’re working in a creative field and trying things that are a little bit unconventional, and people respond, you begin thinking, “Wow! They trust me and they’re interested in what I have to say”—even if it’s orchid poachers in Florida or a dog who has been dead for 100 years. I think people like learning interesting things and they like hearing narrative. Over time I’ve come to trust in my capacity for that, and I’ve seen the reaction. So it feeds on itself.

Q. Aside from curious, how else would you describe your character? How else do you think of yourself?

A. In my writing persona or in my personality?

Q. Your whole self. I’m sure your writing persona is a huge part of that.

A. Yes, there’s not a huge gap between what I am on the page and what I am in real life. For some lucky reason, I am really open. I’m opinionated but I’m not judgmental, which I think of as a very different impulse. I have a lot of energy, and I’ve been lucky that I can step into worlds that are very different from my own and feel comfortable and empathy in those other worlds.

Q. Is there a career lesson you learned the hard way?

A. Never do something for the wrong reason. If you take on a project for a reason other than what you really are comfortable with, it’ll come back to haunt you. There are plenty of things we all have to do—in every profession—that are not necessarily the thing we dreamed of doing, but having a sense of why you’re doing it and being comfortable with that seems to me essential.

Even if the reason is simply: “I need to earn some more money and I’m going to do this project because it pays well.” That’s a perfectly authentic, reasonable choice to make. But you do need to know that’s why you’re doing it and be honest with yourself. Every time I lied to myself about why I had chosen a certain project, it turned out to be incredibly difficult and unsatisfying.

Q. Let’s talk about story choice. Do you find that in order to pursue a story, you need to initially have some sort of spark, some sense of why it’s important and meaningful? Or do you pursue something precisely in order to figure out what’s interesting that you can’t yet see?

A. I think story choice is a little like dating. You meet somebody and you don’t necessarily immediately project into the future 20 years, but you need some spark. You need some click. And the fact is, often you can’t even articulate what that is.

With stories, I feel that very much. There’s not a focus group that goes on in my head, thinking this will be a good story because people will want to read it. None of that. It’s some purely visceral reaction that I have where I think, “Oh, that’s interesting.” And then the next click in my head needs to be: I could see where that could be a story.

I’m perfectly happy knowing nothing about the subject. In fact, that’s usually much more appealing to me. What really matters is that I want to learn more.

Q. You became a staff writer at The New Yorker a little more than two decades ago now. What have you seen change in that time?

A. The New Yorker has been surprisingly constant over its entire history, which is kind of remarkable. For the writers, though, there’s been a bit more of a framework created to help people stay productive. When I first came to the magazine, there were no deadlines. For some people, that was incredibly glorious and liberating. For other people, it was really oppressive.

[Want to hear her advice on writing for the New Yorker? Listen to that and more in the podcast]

There were many writers when I got to the magazine who hadn’t produced anything in years. It’s not that they were lazy. It’s that in many cases they were crazy perfectionists who, without a deadline, simply continued working and polishing and tweaking. Without any sense of a deadline, you could work on something forever.

Q. Are you in that perfectionist category?

A. Yes and no. I could report forever, because there’s always more information to learn. The deadline helps me say, “I may not know everything, but I know enough to be able to tell the story.”

As for the writing part of it, at some point I’m so sick of the thing that I can’t wait to get it off and let it have its own life. When I worked without a deadline, as I did for a number of years at the magazine, I gave myself a deadline. I just found it very strange not to have an endpoint that I was aiming for.

Q. Did you come up with other techniques as well to discipline your writing?

A. I absolutely treat myself like a factory. A word factory. That’s been really helpful for me because writing is very mysterious, and the creative process is very mysterious. It’s comforting to have a few mechanical tools at hand to help balance that sense of mystery.

First of all, if you don’t have a deadline, give yourself one and take it seriously. Secondly, I am thoroughly dependent on having a daily word count as a goal that I have to hit. If I get it done in an hour, I have the afternoon off. If it takes me until midnight, it takes me until midnight. The value of that is it makes concrete a process that otherwise seems ephemeral.

It also means you can look at a calendar and say, “If I’m writing a 100,000-word book, I will be done on this day if I keep my schedule going.” You’re no longer looking into the void and thinking, “Oh God, it’s me and this blank screen.”

I also think if you’ve got writer’s block, you don’t have writer’s block. You have reporter’s block. You only are having trouble writing because you don’t actually yet know what you’re trying to say, and that usually means you don’t have enough information. That’s the signal to walk away from the keyboard, think about what it is that you don’t really know yet, and go do that reporting.

Q. Typically what is the first thing you do once you’re ready to start writing? Are you someone who maps out the arc of the story, or you just start right in with composing the first line?

A. A little of both. The first thing I do is I review all my reporting. In the case of working on a book, you’re talking about an enormous amount of material that has to be reviewed and organized. I have a very clumsy, very analog system of producing index cards for each significant idea. I use those to help lay out the structure of the book. On my last book, for instance, I had more than 700 index cards. When I’m writing a magazine piece, I type up the significant parts of my notes and then lay them all out to see what the structure is, how it would flow.

But I write from the first sentence through to the last. I really begin at the beginning. What that reflects is that there’s very much a storytelling quality to the work that I do. I feel that I can only create that tone by producing it as a story from the beginning through to the end.

Q. Who have been the most influential people in helping to shape your career?

A. I’ve been very inspired by a lot of the greats of literary journalism: John McPhee, Joan Didion, Joseph Mitchell. I’m inspired by the fullness of their writerly personas living in their work, and it’s made me understand what being a writer really can be.

I’ve also had great mentors. I happen to think that being edited is one of the greatest experiences you can have. It’s a luxury to be in a profession where someone can help make your work better. I had an editor at The New Yorker for almost 10 years, Charles McGrath, who really turned me into a grown-up writer. I was somebody who came to the magazine filled with a lot of energy and a lot of enthusiasm, but he really made me a writer.

Q. How did he do that?

A. He liberated me from a lot of the conventions of storytelling that I thought you had to do. He made me feel that I could actually tell the story in a more natural way, and that it would be more powerful.

He was a great, rigorous editor as far as removing excess verbiage and the little writing ticks you have when you’re getting started, but he really made me feel like I was a storyteller. That was the greatest thing that I could feel—and the more that I believed in it, the more confidence I had about my writing.

Q. You’ve published several books by now. What have you found most frustrating about the publishing industry, what you would change?

A. Everything! The publishing industry has been good to me, but it’s a frustrating business filled with a lot of outdated systems. There are certain conventions in the way a book gets published that people do even though there is no science behind it, no particular reason we keep doing it that way.

I’ll give an example, which is the miserable process of getting blurbs for books. Everyone hates asking for them. Everyone hates writing them. And there is no reason to believe that they actually sell books. As an author, the amount of energy you put into that is surprising.

While that’s not a huge piece of the business of publishing, it’s an example to me of some of the touchstones that we haven’t really looked at and thought, “Okay, this is time consuming and what does it do, really?” Book tours are similar, and the reality is that people do fewer of them because we know that they don’t really sell books.

I’m lucky because I have a great publisher and a fabulous editor, so my concerns are more about how books are marketed, how they’re pushed out into the world. I’m not sure that we’ve reinvented that for the world that we’re in now.

Q. Leadership isn’t a term you hear a lot in journalism and writing, the way you hear it in business. What does leadership mean to you, in your field?

A. I think leadership is actually incredibly important in journalism, precisely because it’s a creative endeavor and there aren’t benchmarks that explain what success is to a writer. Having an editor-in-chief who has a mission, who is able to give writers a sense of purpose that supersedes the net profit and loss of the publication, is really important to a writer.

The process can be very solitary and very lonely and very frustrating, so there’s a comfort in knowing that you’re part of something bigger. I absolutely think strong, compassionate leadership in those institutions is crucial.

Q. What’s a book you read recently that you loved?

A. I just read a fabulous book called The Age of Ambition, which is about China. I also just finished Station 11, which I thought was magnificent, and before that All the Light We Cannot See, by Anthony Doerr, also just a beautiful book.

I also recently read a book by William Maxwell, a longtime New Yorker editor and writer who passed away, called So Long, See You Tomorrow, set in the Midwest. It was one of the most beautiful books I’ve ever read.

When I read a great book, the feeling that I have as a writer is, “This is magic.” It’s magic to write something good and to give someone outside of yourself an experience that is so emotional and so evocative and so transporting.

Q. Speaking of emotion, you have a podcast called “Crybabies” that explores what makes people cry. Is that something you consciously think about when writing—how to pick and construct stories that will resonate emotionally with people?

A. Absolutely, 100 percent. I think the greatest motivator for me as I’m writing is to take a reader through a cycle of emotions in a story. Yes, there is intellectual value. I want you to learn about something interesting. But what I’m really hoping is that you travel an emotional circuit.

I actually like writing sad things. I like the idea that someone could be moved (and making them laugh is also moving them). Having that resonance—writing something that can perhaps even makes you tear up—really matters to me.

Q. What’s the best piece of advice someone else has ever given you?

A. Wear sunscreen. [Laughs] I got a lot of great advice from my dad. I’m sure lots of people say that, but my father was really, really the author of my particular personality. He gave me a million different pieces of advice, but one that comes up all the time is: Anything that can be fixed with money isn’t worth crying over.

In other words, the things that really matter, that really should move you and concern you and take a lot out of you emotionally, are not the things of the material world that can be simply fixed by throwing money at them. To me it was sort of spiritual in its point, which is that there are big things that require a lot of you, but those are different things.

Listen to the podcast:

On Leadership: A conversation with Susan Orlean

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