How Cheryl Strayed's Book of Advice Columns Made the Jump To Off-Broadway—and Even HBO

Once upon a time, Strayed dragged an email from Hamilton director Thomas Kail into her "to-do" folder.

Six years ago, Cheryl Strayed's writer friend Steve Almond approached her with a proposition. Would she like to take over an anonymous online advice column he'd been writing? Under the name "Dear Sugar," Strayed interwove her own heart-wrenching, angry and fucked-up life experiences with answers to questions like: "What would you tell your 20-something self if you could talk to her now?" The column quickly developed a cult following, and in 2013, she received an email from Hamilton director Thomas Kail. She did not answer right away.

This was when Strayed was busy with the paperback tour of Wild, which had made the New York Times bestseller list within its first week of publication, but had not yet been made into a Golden Globe-winning film adaptation. While still editing Wild, Strayed had compiled her columns into the full-length part memoir, part advice book Tiny Beautiful Things. Kail read the book and reached out to Strayed about adapting it as a play. She dragged his email into her "to-do" folder.

Related: An Oral History of the Wild Boot

"I don't even know why I have a to-do box," Strayed says. "Who ever does what they're supposed to do?"

She promptly forgot about the email. But seven months later, Nia Vardalos posted on her Facebook page that she wanted to work with Strayed and Kail, a friend of hers, to turn the book into a play. Both Strayed and Vardalos happened to be in L.A. that week, and when the two met for tea, they decided to go forward with the play. Strayed relinquished control of the adaptation to Vardalos and Kail.

Strayed had already practiced letting go of her own work. "What I found with Wild is to sit back and let those artists express themselves," she says. "We read books differently than we sit in a room watching live theater. You can't sit there all day watching the performance." Many people probably would, though. The off-Broadway play, which opens in November, stars Vardalos as Dear Sugar, in what Strayed calls "columns brought to life." The play sold out its seven-week run in a few hours.

Related: Cheryl Strayed says she'll fight to have TV version of Tiny Beautiful Things filmed in Portland.

The TV proposal was born not out of tea, but late-night drinks in London. Strayed, Witherspoon, Laura Dern and one of the producers of Wild were looking for another chance to work together, so they decided over cocktails to create an episodic TV drama about an advice columnist who lives in Portland and is in her 40s. It's fiction, Strayed insists.

"We're completely free in the world of fiction. She'd be a friend of mine, but she is not me," Strayed says, who's writing the show, along with her husband Brian Lindstrom. "The columns will be used in a different way…a little more sidelined. You're not going to watch TV and have the column laid out before you."

But writing a TV pilot for HBO is a new challenge for the seasoned writer. "I sort of laugh at myself because I'm such a prose writer," says Strayed. "I want to describe how the soap in the dish looks and the room smells. Then, I'm 10 pages in and nobody has said anything."

Strayed says she has to follow her own counsel when writing: "It's me taking my own advice and saying, 'OK, you can do this.'"