Cheryl Strayed talks 'Wild,' 'Tiny Beautiful Things,' Oprah, and 'Dear Sugar'

When Cheryl Strayed initially set out to write about the three-month hike on the unforgiving Pacific Coast Trail that she took at the age of 26, she expected it to be a long essay. It turned into a memoir, Wild, somewhat on accident, and now it’s an Oprah’s Book Club pick, sitting at No. 1 on the Hardcover Nonfiction list.

Before Wild became a major best-seller, Strayed was an accomplished essayist and novelist (2006’s Torch), and she already had a large, passionate reader following in “Dear Sugar,” the terrific, at times brutally honest advice column she’s been writing for therumpus.net since March 2010. She wrote as Sugar anonymously until she outed herself in February of this year. Vintage has released Tiny Beautiful Things, a paperback collection of her advice columns, some of which haven’t been published before.

Very much in demand these days, Strayed has been traveling the country talking to fans of both her new books. She took a moment to talk about Oprah, Wild, and Tiny Beautiful Things. She also has some helpful advice to all the aspiring writers out there.

Were you surprised by the success of Wild?

When I was writing it, I focused on doing the best work I could and come what may, so of course I was surprised. When I see Wild atop the list like that, I still think, “What? What?” I can’t truly absorb it. Part of me still feels like I’m in some kind of alternate reality, a science fiction novel. It’s very strange. It’s delightful, but it’s very strange, too.

Was it surreal sitting down and discussing your book with Oprah for hours and hours?

Yes! That was a little weird. But honestly, what was so weird is that Oprah is exactly how I thought she would be. For years, watching her on TV and seeing how funny and warm and authentic she comes across on TV, that’s how she is in real life also, only more so. When I first sat down with her, my first thought was, “I’m sitting down with Oprah Winfrey! What is this?” Pretty quickly that fell away, and I was having a great conversation with an intelligent woman. She wasn’t “Oprah Winfrey” in capital letters. She was a woman named Oprah.

“Dear Sugar” and Tiny Beautiful Things are so great. Do people feel free to approach you and ask for advice now?

To some degree. What’s funny is that the group of people who ask me for advice most is reporters and radio interviewers. [Laughs] They’ll ask, “Are people asking you for advice?” And then they go, “Because I was thinking there’s something I wanted to ask you.” It’s really funny — I’ve given a lot of reporters advice, so if you have any troubles, I’m happy to help! And, obviously, my friends, because one of the things you do with friends is counsel each other. But I have had some people write to me and say, “I’d like to talk privately with you because I have a situation and I don’t want it to be published in the column,” and of course I can’t do that. The whole reason I’m writing that column is really to help people, and to write something and create a public document, so I try to get out of giving too much individual, personal advice unless somebody’s actually my friend.

Fans of “Dear Sugar” are unbelievably fervent. If you look at the comments on one of your columns, the readers even start sounding like you. Why is that?

That’s the thing that really struck me early on. There was something about the way people responded to Sugar that’s on a different level. It’s a more fervent level of fandom, and I think it is because it’s so personal. People who are writing to me are really, truly writing to me for real about their actual sorrows and secrets and struggles, and I’m responding likewise. I’m responding from a really true place and talking about my secret sorrows and struggles. I think it just creates a really intimate exchange, so when people do read it, they feel like they’re being brought to a place where we often aren’t brought, especially in a public forum and especially on the internet. It’s very personal. It’s not just an entertainment. They feel that they’re having an emotional experience with the work.

There was a whole community that was really built around the column online and now that Tiny Beautiful Things is out in the world, I’m starting to get e-mails from readers who’ve read the book, and it’s a very similar kind of expression. It’s interesting because people do the same with Wild. Wild is also a personal book. I mean, in most of my fan mail, the first sentence or two is about the book, and then the rest — the next 5 or 6 paragraphs — is a story from that person’s life, people sharing their lives with me very personally.

What was the column from Tiny Beautiful Things that was the hardest to write, the one that caused you the most doubt?

I would say the “Obliterated Place,” which is about a man whose son was killed by a drunk driver. He was suffering so much. That one really caused … it wasn’t so much doubt — I certainly had words for him, but because I”ve never lost a child, I wanted to make sure I was both acknowledging his pain, which is just tremendous, and also pushing him to go beyond it. There was a piece of me that was going, “Well, what right do I have to do this?” I’ve certainly suffered and lost someone who was really essential to me, my mother. But I do know as a mother myself that losing my child would be on a whole other level. Sometimes it is difficult to talk to a pain that I have not experienced directly. I always take a little extra care. Am I really saying what needs to be said here? It wasn’t so much doubt as agony, that letter, because I was so touched by it. He says, “How do I become human again?” And of course, he is entirely human and anyone who reads that letter of his knows that. So it’s a big question to answer. It was really important that I consider it hard.

Which column was the most fun to write?

I think “Write Like a Motherf—er.” I think was really fun for me to write because I just felt really sure about what the letter writer needed to hear, which was essentially, “Quit your bitchin’.” She was complaining about not being able to write and not being a genius yet, and it was like, “Oh come on, get over yourself.” When I was her age, I too needed to get over myself, and I think every writer does at some point and it’s usually fairly early on in the trajectory. You do need to let go of those notions of your own importance before you do the work. So I was telling her to do that. It was fun for me. Part of it is because in some ways, it was like I was writing to a younger version of myself in that advice. So that was fun. And I got to use the word “mother—er.”

What was maybe the harshest column from the book?

The other writing advice letter in the book, “We Are All Savages Inside” – people have been saying that is the harshest column in the book. It’s not because I was trying to be at all mean to that person. It was just that I know how seriously one has to struggle with envy and jealousy when you’re a writer. That’s a part of the writing life, and here, again, you just have to get over it, and if you don’t, you will fail. It’s like trying to be the prettiest person in the room your whole life, and you can’t be. With writing, I was trying to say to that letter writer, “You know, okay, how much power are you going to give these negative feelings? And how are you going to let them prevent you from letting you succeed because that’s what it’s about.” I came off harsh because it’s something I have a lot of clarity on because I myself. This is what I’ve done for a living. Again, it was almost like advice to a younger version of myself, those two letters about writing.

You’re very in demand for media and interviews. Are you looking forward to getting back to actual writing, and also being a mom?

Oh my God, yes! It’s definitely very challenging right now. I do really want to get back to writing, and I’m hungry for that. But the harder part, for sure, is being a mom to kids who are six and eight. I’m trying to balance the demands of this time, which I absolutely want to rise to. I’ve spent my life working for this moment that I never really dreamed would come true, then here it is. My husband and I said, this is a time when I just have to do my work and it does keep me away from home more than I want to be, but it’s a short period of time and my kids are fine. They’re really resilient and we have quick, intense visits here, there, and everywhere. But I do look forward to things mellowing out a bit and going back to regular life.

What will you write next — fiction or nonfiction?

Both! I think that I will always go back and forth. Before this wild, crazy, Wild year started, I had begun writing a novel that I’m really interested in and I’m really interested in going back to when things calm down. I write personal essays, and I love writing nonfiction and I started a long essay — I don’t know what it’s going to turn into — but I was very deep into that. So I think I’ll pick both of those things back up when I get back to writing. I also have to get back to the Sugar column as well. I’ve been on this hiatus because I’ve been so busy. I didn’t intend to take such a long break, but that’s what’s had to happen. I think throughout my career, I’ll write both fiction and nonfiction because they’re both very interesting to me as a writer.

It’s amazing how broad the appeal of Wild is. I’m 26, the same age you’re writing about in the book. But I just gave it to my middle-aged Korean mother, and I’m sure she’ll like it, too.

It’s so funny. I don’t know how I managed to write a book that people’s mothers like. I’ve had so many mothers give it to their kids. Somehow, all these really elderly people have written to me. I mean, tons! Tons and tons. People are like, “I’m 80 years old, and I read your book.” It’s been such a great lesson to me. Don’t judge a book by its cover. Just because somebody is a certain gender or age or whatever, that doesn’t mean that they can’t relate to essentially the universal human experience. That’s just really touching to me that it’s reached such a broad group.

It also helps that you’re writing about being 26, but you brought perspective to it as your 40-something self.

I never said, “This is my 40-year-old self writing this book.” But it was. The consciousness behind it was not my 26-y ear-old self even though I was absolutely writing about being 26.

Plus, it’s way cooler than the average mom read.

There’s sex, there’s drugs, there’s rock n’ roll!

Any parting advice?

Yes. Write like a motherf—cker!

Follow Stephan on Twitter: @EWStephanLee

Book Review: Tiny Beautiful Things

Amazon picks its top 10 books of 2012 so far

Cheryl Strayed: Hiking 1,100 Miles to a Fresh Start