Before Cheryl Strayed became famous for Wild, her memoir about hiking the Pacific Crest Trail, she was Sugar. Nobody knew it at the time. She wrote the Dear Sugar advice column on The Rumpus, a literary website, without pay and under a pseudonym. People wrote in with their worst problems. Strayed answered them by telling the truth about her own.
This is not a conventional advice book. A twenty-something writes in paralyzed by jealousy of more successful writers. Strayed responds with a story about her own years of paralysis, her mother’s death, her descent into heroin, and the long climb back. A man asks how to deal with his father’s homophobia. A woman wonders whether to leave a partner she loves but is no longer in love with. Each time, Strayed meets the question with an answer that is specific, grounded in her own failures, and stripped of the safe distance most advisors maintain.
The columns work because Strayed does something unusual: she refuses to protect herself. She writes about infidelity, drug addiction, grief, abortion, poverty, and ambition without hedging or performing. The effect is that readers feel they are getting advice from a friend who has been through worse and come out the other side, not from someone perched above them.
The book is organized loosely by theme, but it does not need to be read in order. Individual columns stand on their own. Some are funny. Some will level you. The column titled “Write Like a Motherf*cker,” addressed to a struggling writer, became one of the most shared pieces of writing advice on the internet for a reason.
For entrepreneurs and ambitious people, the book has unexpected relevance. Many of the questions touch on themes that founders deal with constantly: self-doubt, envy of peers, the fear that you are wasting your life, the tension between what you want and what feels safe. Strayed does not solve these problems. She sits with them and tells you what she sees.
Tiny Beautiful Things was adapted into a play staged across the country and a Hulu television series. Strayed’s identity as Sugar was revealed in 2012. The book debuted at number five on the New York Times bestseller list.
