10 of the Best ‘Dear Sugar’ Advice Columns by Wild Author Cheryl Strayed

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Photo: Tim P. Whitby/Getty Images

The last words that Reese Witherspoon utters in Wild come directly from Cheryl Strayed’s memoir (no spoilers, but trust us: You may tear up when you hear them) and will certainly send many people rushing out of the theater to buy a copy of the book. Wild — both iterations — is about many things (nature, infidelity, forgiveness, grief, heroin, finding properly fitting hiking boots), but among them, it is a love letter to words: the words Strayed’s mother said to her before she died, the words in the books Strayed carried with her on her 1,000-mile trek across the Pacific Crest Trail, and the words she finally allowed herself to believe in order to move on with her life and find peace. Strayed’s words are powerful, strong tools, both spoken and on the page, and her ability to say exactly the right thing at the right time may be most apparent in her pre-Wild writing, before the country knew her name. In fact, it was before anyone did: She only went by Sugar.

Strayed started writing the weekly "Dear Sugar" advice column on the literary site The Rumpus in 2010, quietly taking over for writer Steve Almond as the glowing, all-knowing oracle who would answer reader queries with empathy and depth. Strayed had already written and published a novel called Torch, but she chose not to reveal her name for the Sugar project, and it was behind this veil of anonymity that she began to do some of the most surprising, raw, and heartbreaking writing on the internet. Sugar became a phenomenon, and soon she had an army of “sweet peas” clamoring to know her identity.

When Strayed finally decided to unmask herself in February of 2012, I helped throw her a coming-out party in New York at Housing Works Books. I enlisted several fellow writers and Sugar fans to read their favorite columns, and Strayed stood onstage and read a beautiful passage from Wild, which had come out that week. The event was sold out, and there was a line down the block and around the corner — we were all superfans of Sugar long before your aunt was weeping over Wild in book club, and that devotion was rewarded with a book of its own, Tiny Beautiful Things, the collected advice columns. The book is essential, recommended reading, but if you are eager to start your Sugar obsession now, all of Strayed’s Rumpus columns are still available online. (And starting in January, you'll be able to hear her advice in podcast form.) Here are our selections for some of her best work to get you started.

1. Tiny Beautiful Things (on advice to a twentysomething just starting adulthood)
"One Christmas at the very beginning of your twenties when your mother gives you a warm coat that she saved for months to buy, don’t look at her skeptically after she tells you she thought the coat was perfect for you. Don’t hold it up and say it’s longer than you like your coats to be and too puffy and possibly even too warm. Your mother will be dead by spring. That coat will be the last gift she gave you. You will regret the small thing you didn’t say for the rest of your life. Say thank you.”

2. The Ghost Ship That Didn’t Carry Us (on whether or not to have children)
“I’ll never know and neither will you of the life you don’t choose. We’ll only know that whatever that sister life was, it was important and beautiful and not ours. It was the ghost ship that didn’t carry us. There’s nothing to do but salute it from the shore.”

3. We Are All Savages Inside (on insatiable jealousy)
“Awful Jealous Person, there is hope for you. You, too, can be a person who didn’t give up. Most of the people who didn’t give up realized that in order to thrive they had to dismantle the ugly jealous god in their heads so they could instead serve something greater: their own work.”

4. The Bad Things You Did (on finding redemption after doing wrong)
“Years after I stopped stealing things I was sitting alone by a river. As I sat looking at the water I found myself thinking about all the things I’d taken that didn’t belong to me and before I even knew what I was doing I began picking a blade of grass for each one and then dropping it into the water. I am forgiven, I thought as I let go of the blade that stood in for the blue eye shadow. I am forgiven, I thought for each of those fancy soaps. I am forgiven, for the dog figurine and the pretty sweater, and so on until I’d let all the bad things I’d done float right on down the river and I’d said I am forgiven so many times it felt like I really was.”

5. The Magic of Wanting to Be (on being single at an older age and wanting to find love again despite years of baggage)
”I remembered a younger version of myself as I pondered your letter. I recalled a time fifteen years ago, when I was sitting in a café with Mr. Sugar. We’d only been lovers for a month, but we were already in deep, thick in the thrall of the you-tell-me-everything-and-I’ll-tell-you-everything-because-I-love-you-so-madly stage, and on this particular afternoon I was telling him the harrowing tale of how I’d gotten pregnant by a heroin addict the year before and how I’d felt so angry and sad and self-destructive over having an abortion that I’d intentionally sliced a shallow line in my arm with a knife, even though I’d never done that before. When I got to the part about cutting myself, Mr. Sugar stopped me. He said, ‘Don’t get me wrong. I want to hear everything about your life. But I want you to know that you don’t need to tell me this to get me to love you. You don’t have to be broken for me.’”

6. A Big Life (on finding an emotional and financial identity separate from one’s parents)
“You know the best thing about paying your own bills? No one can tell you what to do with your money. You say your parents are emotionally unsupportive. You say you’re weary of their intentions. You say they don’t see you for the vibrant woman that you are. Well, the moment you sign that paper absolving them of their financial obligation to your debts, you are free. You may love them, you may despise them, you may choose to have whatever sort of relationship you choose to have with them, but you are no longer beholden to them in this one particular and important way. You are financially accountable only to yourself. If they express disdain for the jobs you have or the way you spend your money, you can rightly tell them it’s none of their damn business. They have absolutely no power over you in this regard. No one does. That’s a mighty liberating thing.”

7. Tiny Revolutions (on changing oneself in midlife "before its too late")
“Real change happens on the level of the gesture. It’s one person doing one thing differently than he or she did before. It’s the man who opts not to invite his abusive mother to his wedding; the woman who decides to spend her Saturday mornings in a drawing class instead of scrubbing the toilets at home; the writer who won’t allow himself to be devoured by his envy; the parent who takes a deep breath instead of throwing a plate. It’s you and me standing naked before our lovers, even if it makes us feel kind of squirmy in a bad way when we do. The work is there. It’s our task. Doing it will give us strength and clarity. It will bring us closer to who we hope to be.”

8. The Future Has an Ancient Heart (what Sugar would say if she gave a graduation speech)
“It’s really condescending to tell you how young you are. It’s even inaccurate. Some of you who are graduating from college are not young. Some of you are older than me. But to those of you new college graduates who are indeed young, the old new college graduates will back me up on this: you are so god damned young. Which means about eight of the ten things you have decided about yourself will over time prove to be false. The other two things will prove to be so true that you’ll look back in twenty years and howl.”

9. Write Like a Motherfucker (writing advice to a woman who thinks she "writes like a girl")
“How many women wrote beautiful novels and stories and poems and essays and plays and scripts and songs in spite of all the crap they endured. How many of them didn’t collapse in a heap of 'I could have been better than this' and instead went right ahead and became better than anyone would have predicted or allowed them to be. The unifying theme is resilience and faith. The unifying theme is being a warrior and a motherfucker. It is not fragility. It’s strength. It’s nerve. And 'if your Nerve, deny you –,' as Emily Dickinson wrote, 'go above your Nerve.' Writing is hard for every last one of us — straight white men included. Coal mining is harder. Do you think miners stand around all day talking about how hard it is to mine for coal? They do not. They simply dig.”

10. How You Get Unstuck (on moving on after unimaginable grief)
“This is how you get unstuck, Stuck. You reach. Not so you can walk away from the daughter you loved, but so you can live the life that is yours — the one that includes the sad loss of your daughter, but is not arrested by it. The one that eventually leads you to a place in which you not only grieve her, but also feel lucky to have had the privilege of loving her. That place of true healing is a fierce place. It’s a giant place. It’s a place of monstrous beauty and endless dark and glimmering light. And you have to work really, really, really fucking hard to get there, but you can do it, honey. You’re a woman who can travel that far. I know it. Your ability to get there is evident to me in every word of your bright shining grief star of a letter.”