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Becoming Dear Sugar

Author Cheryl Strayed is the anonymous (until now) writer behind the powerhouse advice column

Cheryl StrayedSince March of 2010, writer Cheryl Strayed has had a secret.

Every week, after she has put her two children to bed, she would pour herself a glass of red wine and sit down to write the “Dear Sugar” column, which appears on the San Francisco-based literary web site The Rumpus.

Prior to becoming Sugar, Strayed had never written an advice column in her life; her experience with the medium consisted of infrequently skimming “Dear Abby” and “Ann Landers.”

Now, two years later, her readership is devoted to the point of fanaticism. The column has garnered more than two million pageviews, and counting. Mugs and t-shirts sporting her iconic tagline —“Write like a motherfucker” —have been crucial fundraising tools for the website.

“I thought it wouldn’t interfere with what I had known as my real writing life,” Strayed said. “I thought, ‘this will just be something I do on the side.’ ”

By Strayed’s own admission, what began as a lark has become a phenomenon. But for the thousands of readers who have relied on Sugar’s honest and emotional advice, Strayed’s big reveal poses a question: does destroying the author’s anonymity diminish the experience of reading Sugar? Will the column survive if it’s not “Sugar”?

As one reader put it, “I’m afraid knowing will ruin the magic you’ve created here.”

The regular feature began in 2009 as a side project for Steve Almond, a Boston-based author and essayist who wrote the column’s first 26 installments. During his tenure as Sugar, Almond shaped the persona into a tough-talking, wisecracking trickster – one who warned readers that “insulting questions get surly responses.”

Almond’s Sugar was a modest hit. But when other writing commitments interfered with regular columns, (It was, after all, an unpaid gig) he suggested to Stephen Elliott and Isaac Fitzgerald, The Rumpus’ editors, that Strayed take his place.

At that time, the team debated the merits of keeping Sugar anonymous. In an email exchange between Almond, Strayed, Fitzgerald, and Elliott, Strayed wrote enthusiastically about taking on the role of Sugar, but was ambivalent about whether to remain anonymous. After toying around with a few initial ideas – renaming the column “Ask Cheryl,” or keeping the “Dear Sugar” title but posting her byline at the end of each column – she reached a decision.

“I have come to the conclusion that I think Sugar should remain just as she is: totally anonymous,” Strayed wrote on Feb. 26, just two weeks before her first piece went live. “I like the idea of making up all kinds of crazy and interesting stuff, of really developing a whole life for Sugar, a life that will come seeping out as I answer questions.”

The initial plan was to “be funny” and run with it, Strayed said – to use Sugar’s anonymity as a means of removing herself from some of the responsibilities (and potential culpabilities) inherent to writing an advice column. But as the weeks passed and the questions stacked up in her inbox like Tetris pieces, she found herself turning inward – using her own life stories as jumping off points for conveying guidance.

After a while, she had detailed incidents of sexual abuse at the hands of her grandfather. She had admitted to once being “ridiculously tangled up with heroin.” She had written about her marriage and the infidelity that preceded it, about losing her mother, and about raising her children.

“I began Sugar thinking, ‘I can’t do this. I can’t be as good as Steve Almond,’” she said, “And I really kind of turned it into something that was mine, rather than trying to emulate what he did.”

As she developed her style, Strayed also expanded her readership in jagged bursts. In the column’s 44th installment, “How You Get Unstuck,” she urged “Stuck,” a woman who had recently miscarried, to embrace her sadness. The misery of losing a child, Strayed wrote, is “just there, and you have to survive it.”

Up until that point, “Dear Sugar’s” readership had hovered around 20,000; “Unstuck” was read more than 55,000 times.

Then, just a month later, Strayed fielded a question from Elissa Bassist, a writer seeking advice about her struggles with depression and writer’s block. “How does a woman get up and become the writer she wishes she’d be?” Bassist wrote. Strayed’s answer – a 1,959-word excursion through her own doubts, insecurities and triumphs, ended with a nugget of concise instruction: “Write like a motherfucker.”


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