Rule-Breaker’s Spotlight: Cheryl Strayed

Was it a stroke of marketing genius or a happy accident? Even Cheryl Strayed herself doesn’t seem sure. But whatever it was, it worked—big time.

Three years after the publication of her 2006 debut literary novel, Torch, to critical acclaim but not much fanfare, Strayed was quietly working on a memoir of self-discovery under contract with Knopf when she was approached about taking over as the writer of an online advice column—with a few catches. No byline. No pay. No small time commitment. And no apparent connection (not in tone, subject matter or even audience) to the literary career she was focused on building.

But she said yes.

The column—the thoughtful, honest and sometimes irreverent “Dear Sugar” from The Rumpus—took off. (The title of one installment, her bold encouragement to a depressed writer—“Write Like a Motherf**cker”—went so viral that coffee cups bearing the phrase sold out at this year’s Association of Writers and Writing Programs Conference.) As her memoir, Wild, neared completion, Strayed parlayed interest in a “Sugar” compilation into a second book deal and decided to reveal her identity as the top-secret columnist. The result was a huge promotional wave that drew thousands of thank-you emails from Rumpus readers, launched Wild to bestseller status and built anticipation for the July release of Sugar’s book, Tiny Beautiful Things. Wild has been optioned by Reese Witherspoon’s production company. And many are predicting Strayed’s success could rival Elizabeth Gilbert’s Eat, Pray, Love.

So how did one author assemble an army of fans almost by accident? And what can you learn from her approach?

Strayed’s unconventional publishing path was spotlighted as part of the July/August 2012 Writer’s Digest special “Rule-Breaker’s Issue” feature on “Rewriting the Rules of Marketing.” The following is a special online-exclusive extended version of WD’s Q&A with Strayed.

You could have so easily said, “No can do,” when Steve Almond asked you to take over the “Dear Sugar” column for The Rumpus. Many serious literary writers would have. But you didn’t. Why not?

Because it was fun. There were all these great reasons not to do it. It didn’t pay anything. It was just another thing on the Internet among so many things on the Internet. I was already busy enough. But I felt sparked when I wrote that first “Sugar” column. I said yes because it made my heart thump.

“Sugar” is weekly, and often lengthy. Did you ever question the time it took from your other writing? How did you reconcile the steep deadline curve against a hungry bank account?

It was hard. My husband is also a freelance artist and we have two young children and no family support, so money has been a constant source of stress and difficulty. Sometimes I would think it was crazy spending so much time writing the “Dear Sugar” column for no pay when I could have been writing other things for money, but I kept going. I take the long view. I often say writers are like farmers: the harvest comes, but only after you toil for a few seasons.

The column gave you new opportunities for interactions with readers. Did that inform your other writing?

Yes. Absolutely. [My readers] emboldened me to experiment with the form. When I first started including stories from my life in the column, I was worried that readers would criticize me. But instead they loved it. My most popular columns all have long sections that are essentially memoir. Getting positive feedback from readers gave me confidence to push in new directions in Wild, as well.

You parlayed your initial book deal with Knopf into two deals for books that would enter the marketplace within months of each other. This almost never happens, and surely not in quite this way. How did you convince Knopf to take a chance on Sugar and offer you a second contract with Vintage for Tiny Beautiful Things?

About four months after I began writing the “Dear Sugar” column I started getting emails from editors saying they’d be interested in publishing a collection of my columns. They didn’t know who I was. They would send me an email via my Sugar email address and instead of asking for advice they’d ask me if I’d thought about putting together a Sugar book. At the time I was working on the revisions of Wild and I hadn’t even mentioned the column to my editor, Robin Desser. When I first told her about it, she didn’t seem terribly excited to see a proposal for a “Dear Sugar” collection any time soon. I think she thought it was just this little sideline Internet project I was doing. That changed after she actually read the columns. Once Robin had acquired Tiny Beautiful Things for Vintage, I think there was some anxiety about bringing out two books by the same author so close together, but what fun is life if we only do what we’ve done before? I feel lucky to have a publishing team behind me that likes to roll the dice now and then.

Despite the fact that Wild is from the perspective of a 26-year-old woman, readership seems to transcend gender. In fact, on the book’s Amazon page, it’s featured alongside Jon Krakauer’s Into the Wild and is a bestseller in the categories of “Hiking Camping,” “Nature Travel” and the “West.” Was any of this positioning planned in your proposal process, or did it all evolve later?

I’ve always been adamant about the fact that I write for humans, not for one gender or another. Women writers so often get unfairly framed in this regard. Our stories are cast as particular rather than universal and marketed in ways that make it very difficult to attract a male audience. I was prepared to go to battle to keep Wild from that fate, but I didn’t have to. Men started reading galleys of the book early on—sales reps and booksellers, mostly—and they were excited about it. They weren’t seeing it as a story for their female customers. They were seeing it as a story for them.

You revealed that you were “Dear Sugar” and received a deluge of thousands of thank-you emails. Wild came out in spring 2012 to widespread applause. Tiny Beautiful Things follows in July 2012 and will likely create a second gush of publicity for both books. Reese Witherspoon has optioned rights to Wild and would potentially star in the film if she produced it. This sort of wave of publicity is almost unprecedented. Was it all planned?

I’m amazed and grateful. I didn’t see the wave coming. I don’t think you can when you’re inside of it. From the outside looking in, I suppose it looks like one big great wave that happened all at once. But the experience itself is much more incremental. It started with writing the book. And it ended with people reading it and liking it enough to say to others, “You’ve got to read this.” That’s all that matters to me. Everything good that has happened for Wild (and also the “Dear Sugar” column) can be traced back to the fact that I wrote something I would have written regardless of what sort of splash it did or didn’t make. That doesn’t mean I don’t work hard to help my writing find an audience—I do. And I’m greatly aided by my wonderful publicists at Knopf and Vintage in that endeavor. But that promotional work has to rise from an authentic place or it’s going to fail. Any publicist worth his or her salt will tell you that too.

Can the rave reception your books are receiving set an example for other writers? What advice would you give to writers, successful or aspiring, when it comes to steering their careers toward the limelight while keeping their integrity intact?

When I sold Wild, George Saunders, who’d been my mentor in graduate school, wrote to me and said, “Keep your head down.” I think that’s really great advice, to be reminded that the writer’s task is the work, and the work is the writing. If you keep faith with that, I don’t think you can go wrong. It’s hard to be full of yourself when you spend most days alone in a room with your puny sentences. Professional success does not equal a loss of integrity, though it’s interesting to me that we as a culture often think in those terms when it comes to artists. We tend to consider them most pure when they’re starving and unknown. I feel fortunate to have many successful writer friends as my role models. Most of them have used their time in the limelight in ways that make me respect their integrity even more.

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For ideas for more unconventional approaches to getting your work noticed, don’t miss our complete feature on “Rewriting the Rules of Marketing” and the rest of our special “Rule-Breaker’s Issue” lineup in the July/August 2012 Writer’s Digest.