Photo by Joni Kabana

Cheryl Strayed was revealed this past February as the author behind the wildly popular advice column Dear Sugar. As Sugar, Strayed addresses questions about love, family, addiction, grief, abuse, afflictions, fears, friends, gossip, among other topics — and in each of her answers, without fail, she meets the letter writer with a kind of startling compassion; what Steve Almond termed “radical empathy.” Dear Sugar is an advice column like no other.

Yesterday saw the publication of Tiny Beautiful Things, a collection of Dear Sugar columns. Strayed is also the author of a best-selling memoir, Wild, as well as a novel, Torch.

I spoke to Strayed on the phone about honesty, changing one’s life, writerly success, and the most popular question that Sugar gets asked.

Nika Knight: How many letters do you think you get now, as Sugar?

Cheryl Strayed: Well, I have thousands in my inbox. I have maybe three to five thousand emails that are letters seeking advice. I have a lot.

Do you think you’ll be able to actually read all of them?

I read all of them. There’s no way I’ll be able to answer them all. And a lot of them are the same letter. I mean, that’s the thing — a lot of the letters at this point, too, because I do answer the letters so globally, a lot of the time I’m like, “Well, I’ve basically already answered that.” Like, my answer is — you can just find it in column X or Y or Z.

Is there any question that you’d say you get more than others?

Yeah, I would say probably the most common question is, “How can I recover from this heartbreak?” A lot of twenty-somethings, especially, who have lost that first big love. And they think that their life is over. That their life is very sad and that they kind of don’t know how they’ll ever heal or recover. I get that letter a lot. A lot. And you know, they have all these different details, situations, scenarios, and I’m sure the letter writer — it feels like a very, very original and specific experience, but it’s a very universal experience. Most of us do get our hearts broken in a pretty big way in our twenties. At least once! At least once. And then it always feels like you can’t go on, and yet you do. I haven’t answered that letter a lot, because my answer is, “Oh, you poor thing. But it will be okay.”

There has been such a huge and positive response to Dear Sugar. Was that response something you expected?

I always think, “My work is to do the very best writing I can, in every situation, and then come what may.” I didn’t expect anything to happen with Sugar. I had no expectations. I just did what I did, and then this beautiful thing was born. And I was just amazed by it. Amazed by the response and the amount of love given me in response to the column and the impact it’s had. I mean, so many people have written to me, talked to me and told me that my column actually changed their life. They actually did something or thought something or changed the pattern or left a relationship or started one because of something I wrote. Which is amazing!

Do you hear back from the letter writers?

About half the time I hear from the letter writer. Either they send me an email or [they write in] the comments section, sometimes. It’s always amazing. I’ve never received an email from a letter writer saying — you know, being upset with the advice I gave them. They’ve always been really wonderful, and it’s really great to hear, in some cases, how they took my advice and actually made changes for the better. That’s really cool. I’ve received some really, really beautiful letters from the letter writers.

Do you ever worry about giving bad advice?

I do. I think really hard about the advice I give. I search my soul. And a lot of times I don’t give advice where I’m like, “You absolutely should do this thing.” I try to instead help the letter writers think more deeply and clearly about their situation. But there are some times . . . there was a letter writer who was like, “Should I invite my dad to my wedding?”  And I was like, “No, you absolutely should not.” And I laid out my reasons. Or when I say to people, “Yeah, if you really feel this strongly that you want to break up with this person, you probably should.” And I don’t do that lightly. I always think it all the way through. I make sure that I’m sure about it. And I’m always sure about it when it’s essentially — when I sense really deeply that the letter writer is sure about it, too, but they just need permission or clarity. That they know what the right thing to do is, but they need someone saying, “Yes, this is okay. You can choose this thing for yourself.”

One thing that I think makes the Dear Sugar column so distinctive is that you write these kind of long, personal essays in response to the writer. Was that planned, or did that form sort of evolve as you wrote the column?

It really evolved as I wrote. I mean, I truly was just finding my way along and not exactly knowing how I was going to do it. I just sort of said “yes” on a lark, and then there I was, left to give advice. And pretty quickly I realized, you know, that storytelling was going to be a piece of it for me, because storytelling has been so powerful to me in my own life when it comes to working out my own problems or feeling consoled in my sorrows. And it was also the best way for me, in some ways, to really excavate the complexity of many of the situations that were being presented to me.

And so pretty early on — I mean, if you go back and look, number 27 was my first column, and then it wasn’t long after that that I began to pull in features of my own life and then pretty soon after that I would tell a full-blown story; like a whole, you know, block of what could be described as memoir, really. And like you say, writing these essays in response rather than just a column is kind of a misnomer, isn’t it?

Tiny Beautiful Things reads like a collection of personal essays.

It does kind of form a little bit of an anecdotal memoir.

The form of the advice column seems particularly unusual, in that you’re addressing the letter writer directly but then you’re publishing it for a wide audience to read. Are you aware of both audiences while you’re writing it, or do you just write for the letter writer?

I would say that I’m aware of both. First and foremost, there’s the letter writer. I’m really trying to communicate very directly with the person who wrote me a letter. And so it’s interesting because there’s that intimacy: here’s someone who is writing to me. And even that letter writer knows that he or she is writing to me, but if I choose the letter it’s going to be published and thousands of people are going to read it. Hundreds of thousands of people. Maybe more! And then what I’m doing is replying directly, but mindful that there’s an audience. And so I do always try to really be mindful . . . that, you know, this is an exchange that’s taking place on a public arena. And I try to sort of make — I always take those [specific] questions but I try to make them more global and more universal via my answer. I try to answer a bigger question, a deeper question, and sometimes a more particular question than the letter writer even asked.

For example, in that column, “A Bit of Sully in Your Sweet,” where that woman, you know, she doesn’t know if her sister and her brother-in-law should walk her down the aisle because they’ve had a less-than-perfect marriage. And so it’s like I’m both answering her in my reply, and also making a bigger statement about this whole idea of a perfect relationship. Questioning that, in a bigger way.

One of the reasons that I think the column feels very powerful to me, at least, is the letter writers are so honest and a lot of the times the questions are so deeply personal, and your answers are, too. For example, in that column you just mentioned, you revealed how your own relationship hasn’t been perfect. Are you ever afraid to publish the letters, and your responses? Did it make you afraid to come out as Sugar?

Well, I always wrote the column knowing that I would someday reveal myself. So I always was mindful not to write what I wouldn’t be comfortable putting my name on and being identified with. And so that was helpful. I think that it would have been a very different endeavor if I had decided to be anonymous and made sure that that secret stayed kept. I knew that I was someday going to say, “This was Cheryl Strayed who wrote this.” And so I wrote with that consciousness, in the beginning. And also as you know, when you read Wild, I write very honestly. It was funny, some people would be like, “If you reveal your identity, then you won’t be as honest in your column!” And I [said,] “Just trust me.” Because under my own name, I write that honestly.

To answer your question, sometimes it is very scary and uncomfortable. I sometimes think very hard about what pieces of my life I’m going to reveal, and I don’t reveal all of it. I don’t write about everything. And especially when it comes to invading other people’s privacy — in that column we just mentioned, I talked to my husband about it before I wrote it, and essentially he agreed that there was a story that he felt okay with me telling, even though it definitely gave him a stomach ache, you know? . . . The day it was published, he was like, “Is everyone going to hate me now?” I said, “No they won’t, actually.”

There is always that fear that we’re going to be condemned. And what I’ve learned is when we’re honest about ourselves, we’re usually met with a lot of love. It’s an interesting dynamic, because we do think that condemnation — that we’re going to be met with condemnation when we tell the negative things about ourselves. But I’ve found it to be the opposite.

There’s a line in one of your columns where you say, “this is a lesson I’ve learned over and over again.” A lot of the things that you advise in the column are very basic, like “listen to your gut” or “be a bigger person” or “be kind to yourself” — but they’re lessons that I feel I also continue to learn over and over again. Do you also find yourself having to relearn the the things you advise in your column?

Oh, absolutely. I’ve certainly continued to learn them. All of those things, they’re so basic, right? And you think, “Okay, why can’t I finally learn this? Why can’t I just know this?” . . . And yet they’re so profound. I think it takes all of us a lifetime to truly learn them. I think so often that that advice I give as Sugar is like my best — the best version of myself speaking out of that truth. That’s my true inner voice. . . . And so much of life is learning to listen to that voice, to trust that best self instead of falling back on the worst self. I think that I’m constantly trying to move in the direction where — not so much that I listen to my best self 100% of the time, because I think that nobody probably could do that — but [I’m hoping] the percentage increases.

You wrote a line in one of your columns that I really like: “Change happens at the level of the gesture.” Could you talk a little more about what that means?

I think that’s in my column “Tiny Revolutions,” is that right?


I think the next sentence after that is, “It’s one person doing one thing differently than he or she did before.” So often, at least for me, [this stuff] is so in my head — I think, “Okay, I have to make this change about myself, I have to transform myself in this big and dramatic way.” And really, I think the way that change is more realistically enacted is the things that you actually do; the things you do with your body in your life. Actually having an argument with your partner and being slightly more mindful of how to listen, instead of how to yell. To me, that’s what I mean about that phrase, “change happens at the level of the gesture.”

Or in that case — the woman who feels so self conscious of her body [in “Tiny Revolutions] . . . just one day, instead of allowing herself to think, “Oh, I look terrible,” “I’m fat,” or “I’m ugly,” [if she] just [looked] at herself in the mirror and [said], “I’m okay. I’m okay.” Accepting herself, you know? Even once. I think that’s how change begins. . . . It’s not like she’s going to get this idea and then feel great about herself, but on the level of the gesture she can change. If she can start to, one time, not allow herself to go down that self-hate path, maybe the next time she can do it again. And again, and again.

Since you’ve revealed yourself as Sugar, have people been coming to you in your day-to-day life for advice?

You know, not as much. Certainly, I get all kinds of emails. Sugar gets tons of emails from people asking for advice, but I wouldn’t say that people expect me now to, like, give them direct advice in a way that they didn’t before. Probably part of it is that most of my friends — the people who actually knew me — they knew I was Sugar before I revealed my identity. What’s funny is that I do get a lot of people who interview me, you know, for websites and papers and magazines and stuff — what’s funny is they’ll say, “Okay, now, could you just give me a little advice about this or that or the other thing?” Reporters have been asking me for advice a lot, which always makes me laugh.

But I’ll say it’s been interesting. I kept telling people before I revealed my identity, “I don’t think anything will really change much.” Just because you know who I am doesn’t change the nature of what I do or the column or anything. Some people didn’t believe that, but I think it’s really been true. I’ve only written two or three columns since I revealed my identity, because suddenly my life exploded and I became so busy. But even when I write the columns — if you go back and read the columns written post-reveal, they’re very much — they’re exactly the same. I still write as Sugar, and I don’t talk about — I call Mr. Sugar “Mr. Sugar” instead of “Brian,” you know? I still maintain those kinds of bounds of the Sugar world. And so people kind of maintain them with me, too.

It’s funny, because I have a Sugar Facebook page, and I also have a Cheryl Facebook page — a couple people who have written on Sugar’s Facebook page will address me as “Cheryl,” and a few people have then written and said, “Oh, don’t do that on Sugar’s page.” They’re breaking some kind of barrier, you know? Some boundary. And I see their point. It’s kind of interesting.

Do you think that even though people know who you are, there’s still a kind of persona that exists? A separate “Sugar” persona?

Yeah, I do. It’s funny, because Sugar is me, and the things that I write about as Sugar are things that are about my life. They’re not some imagined thing. And yet, even I can talk to you about Sugar in the third person. . . . What it is is [that] the nature of the work I do as Sugar is pretty specific — just because of it being writing an advice column — so it does feel like it is a version of myself; a slightly altered persona that is incredibly close to who I really am.

You’ve published three books now: a novel, a memoir, and now a collection of advice columns. Was the process very different for each of them?

The process has been shockingly similar. Writing is writing, to me. I throw my whole heart and energy and spirit into whatever it is I’m doing at any given moment, and so I’m really absorbed in that thing. It always feels the same. People will say, “You write both fiction and nonfiction — aren’t they so different?” And they don’t feel different, even though of course each form has its own boundaries and environment and so forth. But it feels the same to me, in the body . . . I’m always trying to create vivid, real, important, honest work. And so it’s just — to me it all feels of a piece. Even though now I think Tiny Beautiful Things is technically going to be classified in the self-help genre, even though it’s also literary nonfiction, because it’s advice. It’s like, how did I become an author of fiction, nonfiction and now self-help? It’s really kind of nuts. And it feels all the same to me.

There was a lot written this spring debating the responsibility of nonfiction to tell the truth — such as the book The Lifespan of a Fact by John D’Gata. How much does truth matter in nonfiction? What do you think about the divisions of genre between fiction and nonfiction?

I definitely am not one of those writers who says, “Well, I don’t think there’s any difference.” When I write nonfiction, I’m definitely drawing on my life and I’m writing it as I remember it, and I try to be as factual as possible. While at the same time saying, absolutely, memoir is a form of subjective truth. This is my remembrance, or my version of a story. And I go to great lengths to be fair to people and to research things I can, but it’s tough. Memory is — it is what it is. It’s my memory, and that’s what I’m writing. And with fiction, you know, the world is open. I can draw on my actual life, but I can also make all kinds of stuff up.

I do avoid doing that in nonfiction, and in my Sugar column, when I write stories of my life — I was always mindful. “Okay, this is nonfiction.” I wasn’t making stuff up. . . . I think John D’Gata with his Lifespan of a Fact was sort of changing facts in ways that make me feel a bit uncomfortable. But I also know there have been a lot of different writers who have been trying to figure out what the form is, still. For me, now, fiction and nonfiction feels the same way, to write it, but I follow slightly different rules with each. The line is: I don’t make stuff up for my nonfiction, and I do for fiction. It’s pretty straightforward.

In one of your most famous Dear Sugar columns, “Write Like a Motherfucker,” you say that when you wrote your first book, you had to let go of the desire to become a really acclaimed or famous writer and just focus on the work. Do you find that that has changed with all of the success that Wild has had, or are you still able to separate the response to the work from the work itself?

It’s more than ever true. And I’m so glad —I really can’t imagine having this kind of success if this were, like, my first book and I was 25 or something. Because I think that I would maybe think, “Oh, this is just how it goes.” I mean, I’m terribly thrilled, don’t get me wrong. It’s just incredibly exciting, all that’s happened, but it definitely feels separate from me, and separate from, in some ways, the work. Which sounds strange. The thing that I really feel is my part of the work is writing the work. And then once it’s out there, promoting it too. But it’s the readers who really — they own the book in a different way. They make it something else. I always try to keep faith in the work itself, and focus on that being my task, and not try to measure my success by those kind of external factors.

When I think about all the many exciting things that have happened around Wild, I remember the day I finished the book. That was the most exciting thing of all. And it would be the same book if two people read it, or if two million people read it — it really would be. And I have a very sure grip on that. When I think about writing the next book, what excites me about it is being alone in a room and doing that kind of work that you do as a writer.

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