Sideshow Podcast: Cheryl Strayed’s “Dear Sugar” is The Internet’s BFF

The internet is doing great things for advice columns. Andrew W.K., T-Pain, and Haruki Murakami are the latest to start life-coaching online, but Dear Sugar, the bygone column at the literary website The Rumpus, remains the fan favorite. “She really has this willingness to share herself in her responses to other people’s problems,” says the writer Ann Friedman, who praised the column in New York Magazine last year. Though Friedman was a Dear Sugar latecomer, she immediately connected with the writing. “It feels like talking it out with a friend – the most articulate, compassionate friend.”

Dear Sugar was launched by the writer Steve Almond in 2010, but it wasn’t long before he handed the reigns over to Cheryl Strayed, who wrote the column until it was retired in 2012. The end of Sugar coincided with the beginning of Wild – Strayed’s best-selling, Oprah-endorsed memoir about hiking the Pacific Crest Trail after years of personal turmoil. The book inspired this year’s Academy Award-nominated Reese Witherspoon movie:

Though Wild has kept Strayed plenty occupied for the past few years, she yearned to return to advice-giving. “I always felt like I had not quite finished my work as Sugar,” she says. When Almond suggested they resurrect the column as a podcast, she signed on immediately. “It sounded like fun to me. And I let my gut drive a lot of my decisions, as I advise other people to do as Sugar.”

Strayed and Almond co-host Dear Sugar Radio and employ “radical empathy” to respond to listeners – a term that refers to sharing one’s own experiences as a way of recommending a certain course of action. “I don’t know the answers,” Strayed says. “But what I can do is help you find a way to ask deeper questions.” After a lifetime of offering stories of her own infidelity, drug use, and woe, Strayed isn’t afraid to over-share. “I’ve always been the person who is interested in going one step further when it comes to risking intimacy,” she says. “I’m sort of famous for being really bad at polite cocktail party conversation.” 

Our Cheryl Strayed interview originally aired on CBC’s Q. Thanks to our friends at Q for letting us make a Sideshow out of the whole affair.