Cheryl Strayed Has The Only Advice You Need This Year

Credit = Photo: Jonathan Leibson/Getty Images for Variety.
Cheryl Strayed fans, rejoice! Just in time for your post-holiday ennui, the Internet has brought us good tidings of great joy: Dear Sugar is back, people. The cult advice column that catapulted Strayed's career has been reborn in podcast form as Dear Sugar Radio, launching this month from WBUR. Though the original column was technically anonymous, Strayed divulged deeply personal stories from her history to respond to reader queries. Cheryl officially "came out" as Sugar in 2012, just before the release of her bestselling memoir, Wild — which then became the gorgeous, heart-bursting film starring Reese Witherspoon. In Dear Sugar's radio incarnation, hosted by Strayed and Steve Almond (who created the column), the pair take on listeners' questions with the same hardcore love and radical honesty that changed millions of readers’ lives.
I got the chance to chat with Cheryl about the new show, the Wild juggernaut, and how she cuts through the bullshit of life’s little (and large) quandaries. If you’re hoping to change your life this year, take heart and leap — because Sugar is back, and she'll hold your hand or shake you by the shoulders whenever you need it.

Congratulations on the movie and the new show! The first episode was so raw and poignant; it really caught me off guard, in a good way. What made you and Steve Almond decide to bring Dear Sugar back as a podcast?
"When I revealed my identity in 2012, I had every intention of continuing the column. But, it was also right before Wild [the book] came out, and I had no idea that it would become this big bestseller that demanded a lot of my attention. So, time passed, and I always felt like I hadn't quite finished Dear Sugar the way I wanted to.

"Along came Steve Almond — the one who had originated the column and asked me to write it. He'd been working with WBUR to develop some shows and suggested that the two of us do Dear Sugar Radio together. People still write to me as Sugar, and I have thousands of letters, so I just picked a few to answer, and it became the first show."

Does it feel different to do the podcast without that veil of anonymity you had with the column?
"No, I never felt like I was writing through a veil of anonymity. I know that other people experienced it as such, but I was always very clear from the outset that I would put my name on those columns, someday. So, it never felt anonymous to me, if that makes sense.

"But, this is definitely a different form. I really crafted those columns. I spent probably eight hours on each, making sure each sentence was worked over. On the podcast, it’s a discussion. In conversation, you say things you didn't think you were going to say.
"I’m always like, ‘Okay, Cheryl, you better watch it. Don’t say something you regret.’ Because, I don't put my guard up. I just say what I think, you know? So, I have to be careful because we're still sharing stories about our lives in this podcast. For example, I talk about my marriage. When I was writing about my marriage in the Dear Sugar column, I would have my husband read it and ask him if he was comfortable. Now, I'm just mindful that I don't want to blurt out something that could be hurtful to somebody in my life."

I often write about personal issues on our site, and it’s a double-edged sword. It creates such intimacy with the reader when you expose your own deep, dark corners. But, there are ramifications in your personal life because there are other people in those deep, dark corners with you. How do you feel about that self-exposure in writing your memoir or doing the podcast?
"There's no question: That’s the hardest part of it. I mean, it really is. I care deeply about not hurting people and not invading their privacy. There are a couple horrible people in my life [laughs], and I have a right to speak my truth about what they did. In one case, I didn’t talk about it at all, and in the other I did it very carefully, because of the various consequences.

"Sometimes, it's just not worth it. Both my siblings, for example, have gone on incredibly difficult and interesting trajectories that would be rich fodder for Dear Sugar. And, I have not really written about them in full, because I don't want to invade their privacy and hurt their feelings. Then, there are other people, like my father, who is alive. He was abusive, and I don't have a relationship with him. I speak about him openly, but also carefully. Because, it's kind of unfair. Unless you're talking about another writer, they don't really have that same ability. They can lash out at you on Facebook or whatever, but they don't have a column where they can write about you. So, I do consider it deeply. I ask myself, ‘What's my story? What stories do I have the right to? And what stories don't I?’"

Right; you don't want to blow up somebody else's life because you're sharing their secrets.
"Well, unless if it affects your life. There's where it gets complicated. There are some things I wrote about my brother in Wild, where if you read carefully, you can surmise some of the struggles that he may have had, which impacted me as well. But, with each draft of my memoir, I took stuff out about him. Because, I didn’t have the right to tell the world his story.

"With memoir-writing — and also in advice-giving — there are consequences, both for you and the reader. What if you suggest something and they do it and it’s disastrous? That’s why I don't often tell someone directly what to do. I usually address the larger issue — the question beneath the question they have. The hardest questions are always like, 'I'm pregnant. Should I have an abortion, keep the baby, or give it up for adoption?’ I could never tell you in a million years what to do, because it's really all on you."
Photo: Courtesy of WBUR.

Another great thing about Dear Sugar is that you honor that ambivalence and uncertainty. For example, in the first episode, you and Steve discussed the quandary of possibly having a third child in your respective families. You wound up in different situations there.
"Yeah! And, the thing is, we were both right. Steve and [his wife] Erin would be fine if they'd decided to have just two kids, and Brian [Cheryl’s husband] and I would be fine if we'd decided to have a third. Something different happened in each of our lives. So much of life is like that. Trust me: The year I was 40 and thinking, Do we want a third child? I spent days agonizing over that question. Now, I can have a total nonchalance about it. It would have been fine if we'd had a third child. I would just be slightly more grumpy right now than I am already [laughs]. I would also have this other person I love madly. You know what I mean?

"I think, in the moment, we forget that usually everything's gonna be ok. These things will figure themselves out. I've been reminding myself of that so much lately."

"Oh yeah. Like, whenever I worry about my kids — wondering if they’re spoiled, if they’re brats, or why aren’t they listening to me. I think, Okay, are they probably going to be fine in 10 years? Yes. The answer is always yes.

"We get all upset about the daily stresses. Is this issue going to be that stressful next week? Something's going to happen. You're either going to get that damn essay in on time, or you’re not. And, what if you don't? What's going to happen to you? I try to have perspective. The older I get, the more I have it, which is one of the great advantages of getting older. Sometimes, the moment feels difficult, but life moves on, and you're usually fine."

That's a good reminder, because we make a million little decisions every day. Sometimes, it feels make-or-break, but when you step back and frame it in the long term, everything changes.
"Yes. Another great thing about the long view is that it allows you to figure out what your real feelings are. For instance, friendships. You know, when you're really annoyed or offended by a friend in the moment? Sometimes, I'll think, What if I got a phone call and found out that they died? What would I be feeling at their funeral? Usually, I realize that I would just be feeling how much I love that person, and how awesome that person is. It really helps you forgive the imperfections of life, when you take a longer view."

Sometimes, I'll find myself answering a reader email or giving a friend advice that I, myself, really need to take. Do you ever find yourself in that situation?
"Oh, all the time. These questions I get — they're the stuff of life, including my own life. For instance, all these questions about love and long-term relationships. So many people write to me and say they love their partner but they’re not in love anymore. They haven't had sex for ages. The romance has gone away. You hear this over and over. And, the problems are each different, but the baseline question is always the same: How do we keep romance and sex alive over many years in monogamy? That is a huge question. I want to answer it, not just for the listeners. I've been with my partner for 19 years; Steve has been with his for 15. We're there, too. How do we do this?

"One of the most beneficial aspects of Dear Sugar is that no one is talking to you from above. Sometimes, with the newspaper columnists, like Dear Abby (whom I have so much respect for), the format demanded that she at least seem to be like a superior moral being. I never wanted to put myself in that place.
"But, there are other times when I respond from a place of experience. For instance, in the column titled, 'Write Like A Motherfucker,' or 'We Are All Savages Inside,' which is about professional jealousy. I'd been through those things and came out the other side, so I do know the way out of that problem. Those are my most stern columns."

Well, it's helpful! The high horse is helpful when you have it available to climb up on.
"Right, and the only way that I got to the high horse is that I had been down in the mud, just like the letter-writer. In those cases, I was like, 'I'm going to give you a talking-to. Here's how you succeed. Not by sitting there, whining about what you think you deserve.’"

The New Yorker once wrote that many of the readers appear to be seeking your validation or attention, and maybe even your scolding, rather than advice, per se. Do you see a lot of that in the letters?
"Sometimes, yeah. People came to trust Sugar as someone who would be both loving and honest. Scolding might be too strong a word, but…no, you're right, I was scolding in those letters. But, it wasn't condemnation. It was affirmation. Sometimes, affirmation can be harsher than we think it is.

"I always wanted the column to be helpful to people. But, we so often see self-help in this kind of soft, entitled, unchallenging way. Like, 'whoever you are, that's okay.' I do think that whoever you are, that's okay. And, I also think you can do better, and you should. I'm not into thinking, ‘Oh, wherever you are, that's the place to be.' I think that that can lead to some really nasty shit. Some of the most entitled assholes I've ever encountered thought of themselves as evolved hippie children of the new age. Give me a right-wing republican over that any day. At least they’re not congratulating themselves on being emotionally evolved while at the same time pushing everyone else out of their way."

It’s true. Sometimes, self-help can foster a kind of narcissistic passivity.
"Yeah! So, I do think you should accept yourself. And, I do think that you should strive to be better. And, I include myself in that. You always need to be conscious of the ways in which you are in contradiction to the ethical or moral values that you espouse."

I think of the columns as something akin to a firm shoulder-shaking. Often, it's as if you're saying, ‘Come on, you know the way. Be honest.’
"Yup. So often in the questions, people basically tell me what they already know to be true. They're just afraid to know the truth. ‘I know I need to do this, but it's so hard.’ They need someone to say, 'Yep, it's hard. It's hard, but you've gotta do it, because it's harder not to.' You reach that point in your life where it's harder not to. Some people spend 50 years waiting to reach that point. Some people never do it. But, you always know.

"I think giving advice is just helping to hurry people along toward the good thing. I see it all the time. There you are, over in that hell pit. All you have to do is step over here, and then you’re not in it. This is the rest of your beautiful life. Step into it. Yes, I know it's hard to step into it. And, yes you can, and you must. Or you're going to live your life in the hell pit. It really is that simple. The biggest change is so, so simple. It really is."

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