Cheryl Strayed on How to Get Started

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Brian Lehrer: Brian Lehrer on WNYC, and during our fall pledge drive, we'll be hearing from our favorite professional advice givers, as part of the show, on thorny topics you might need help with like relationships, finances, and etiquette. Today, we're kicking off the series with writer Cheryl Strayed. You may know her as one of the Sugars from the Dear Sugar advice columns, and podcasts, and author of the bestselling book, Wild, a memoir about her 1100-mile hike on the Pacific Crest Trail, inspired by the grief of losing her mother.

Well, after nearly two years of the pandemic, we thought Cheryl would be among the best people to answer your questions about how to transform pain and darkness-- or even if you're not in pain and darkness-- into something generative and creative, so here, with me, now, to answer your core questions about the creative process, both in art and problem solving, is Cheryl Strayed, bestselling author of Wild, Tiny Beautiful Things, and Brave Enough. Hey, Cheryl, thanks so much for doing this. Welcome back to WNYC.

Cheryl Strayed: Thank you, Brian. It's a pleasure to be here.

Brian: Listeners, do you have a question for Cheryl Strayed about the creative process, including how it's been affected by the pandemic? 646-435-7280 is our on-air line, not our pledge line for those questions. Maybe you can't get yourself to sit down and start, but you want to, what's keeping you from doing it in whatever your creative medium is? Is it your job? Your relationship? Is fear getting in the way of being the creator that you think you can be? Maybe you're having writer's block right now, and that's why you're listening to the show. Call in and tell us about it, 646-435-7280, 646-435-7280, if you have a creativity advice question for Cheryl Strayed.

Cheryl, as some calls are coming in, last year, when the lockdown was really in effect, people said, "This is a great time to write a novel, screenplay, book of poetry," but I think for a lot of people, it was actually hard to be creative, as it turned out. Right?

Cheryl: Absolutely. I think a lot of times, we tend to talk about experience during the pandemic in this way that is kind of uniform. Different people had different experiences in all kinds of ways, but especially in creativity, for some people, I think this was an opportunity for the first time, perhaps in their adult lives at least, to tackle that big project or think more deeply about what direction they really want their life to take professionally. Other people were wildly distracted and found it really hard to write, or to make whatever art they do, whatever kind of creativity is theirs, found it very challenging.

Because, for example, in my case, I'm a writer, I suddenly had two teenagers home all the time, doing online school. I had to keep working and writing, but it was harder than ever, because there were so many distractions and other obligations.

Brian: A great Dear Sugar question on this topic came to you from a then 26-year-old woman named Alyssa. She calls herself a pathetic and confused writer who can't write. She also criticized herself for when she could write for, "writing like a girl" about emotion, about love. I'm curious how much that characterization surprised you that she would admonish herself for writing "like a girl".

Cheryl: It didn't surprise me at all, because those were some of the things I struggled against as a writer, and I think that a piece of that is obviously specific to gender. I think for a long time, women writers have been told that their material isn't the kind of universal experience of great American literature, and so we've had to battle against that, but I think that it really applies across the board. So often the things we feel most driven to explore creatively, we have to find a way to give ourselves permission to explore it.

For whatever reason, one of the anxieties so many creative people have is like, "Well, who's going to care about my story? Who's going to want to hear about my experience? Who's going to want-- fill in the blank-- whatever it is I have to offer?" I would say that that is one of the first barriers, when thinking about how to be creative. You really have to believe that it doesn't matter. You don't have to answer that question.

You don't have to say, "Well, here are all the people who are going to care." What you have to do is care enough that you make it in the world and then accept that the world will receive it however, it wishes to.

Brian: It's a tension, I guess, for creative people. How much are you being other-directed and thinking, "I'm writing because I want to write," or whatever your creative medium is. "I'm writing, I'm composing, I'm painting, I'm doing-- whatever-- because I want other people to like it," versus, "There's something side of me I need to express."

Cheryl: Yes. It's the ultimate tension, and it's completely understandable. All of the ways that we sort of mark success have to do with acclaim, and money, and fame, and recognition. When you're endeavoring to do creative work, you really have to accept that your work, your main task is to make the art, whatever it is, and you do not have control over the way it's received. This is the history of art and literature, by the way. There are so many great writers and artists we love, composers-- the list is endless of people who in their time didn't receive the recognition that they had hoped to receive.

You do really have to keep faith with the work itself and take pleasure in the creativity. I want to just put an asterisk next to pleasure. Making things is often also agonizing. I don't always love to write. In fact, I seldom do, but I know that it's my call, and so I keep faith with that and do it.

Brian: We saw that the culmination of your advice for Alyssa was not something we can say on the radio in full, but you said, "Write, not like a girl, not like a boy, but like a mofo," and I can't say that whole last word. We did just check Alyssa's Twitter, and just recently, she published her first book. Yay. She thanks you for getting her there, and her pin tweet is "Write like a mofo."

Cheryl: That's right. I was just going to mention that, that Alyssa, like so many people, me included, who have agonized and struggled, and thought we would never cross that finish line, or thought we couldn't do it. we couldn't do it, we couldn’t do it. went ahead and did it. I think that that's always the challenge, and I have to say, even as a published writer myself, you'd think that now, I'd be just sailing along, writing that next book, and everything's easy. It's not. During this last year, or during the pandemic, I wrote a feature-length screenplay. I've written a whole bunch on my next book, and I've written some short stories.

I've done a lot of writing, and all of it was hard. All of it, I had to ask those same questions that Alyssa asked me, honestly, "How do I do this?" At the end, that core question is who is going to care? My answer is, that's not the question you need to be asking. It's, "What is my work?" and, "How am I going to find a way to get it done?"

Brian: Listeners, we have time for a few creativity advice questions for Cheryl Strayed. Maybe you read her in Dear Sugar or heard the podcasts. 646-435-7280, as we go through some of the pieces of advice that she's already given to others that we find particularly interesting. 646-435-7280. If you want access to Cheryl Strayed directly for yourself, 646-435-7280. Or you can tweet your question @BrianLehrer. One of the last Dear Sugar columns you co-wrote for the times was to a questioner who wanted to write a memoir but was afraid of what it would reveal to their parents?

The author had trauma that they never told their parents about, and your advice, "Focus on writing, not publishing." That's an interesting distinction.

Cheryl: It's really what I'm trying to say here earlier. I think that we can get ahead of ourselves. So many people want to stop themselves before they write the thing, because they're so afraid of the consequences of what they write. What I've learned so often as a writer is that the first draft is in some ways the truest draft. Get it all out there. It's just yours, it's a private document. Then you think about, "Well, what are the consequences of publishing this?" I want to say that sometimes we think there will be negative consequences, when that's not the case.

Sometimes, relationships could use a little bit of honesty or openness, or that you tell your parents about an experience you had, and that could make you closer. One thing, I restarted the Dear Sugar column about a year ago, Dear Sugar is now a Substack newsletter. I have so many emails from people really standing on the edge of that kind of, "I want to be creative," and maybe the pandemic has put more people in a situation, where they're thinking about that and exploring that. So many of them really talk about fear first. Fear that people around them will judge them, fear that they won't be good enough, fear they won't succeed.

What I want to say, this is a really important central piece, I think, of being a creative, is to understand that fear is part of the process. It's actually telling you that this is an important endeavor. Instead of letting that block your way saying, "Fear, sit down beside me, I'm going to be afraid while I do this thing, but I'm going to do it anyway." You always have to decide, is fear going to be your ruler?

Brian: Julia, in Greenpoint, you're on WNYC, with Cheryl Strayed. Hi, Julia.

Julia: Hi. It's such an honor to talk to both of you. I love you both.

Cheryl: Thank you.

Julia: Of course. I want to talk about distractions, because I'll know, I'm really excited, I'm not fearful. I want to start the work. I'm a writer and a house [unintelligible 00:10:57] designer, and whatever I'm doing, if the space isn't tidy enough or-- something's always going to distract me. I almost feel like I need to make it perfect to then begin the work so that I'm devoid of distractions. Then I spend the whole day reorganizing my studio or sharpening and all my pencils. I'm not usually like that in life. I can let things go and be casual, but when it comes to creativity, it's like I can't even get into that, if there’s things distracting me, even physical things in the space.

I wonder if that's something that you deal with before even sitting down at your desk or wherever you write.

Cheryl: Yes, Julia, you are so, so not alone in that struggle. I think that it really is ultimately about an anxiety, about starting the work, settling into the hard thing, and it is hard work. One of the things I said in the column that Brian referred to earlier that we can't name because it has a swear word in it-- [crosstalk] thank you. Writing isn't coal mining. There are the harder jobs, I guess, but writing is hard, and creating, painting, music, fill in the blank. The reason is you are making something where there is nothing. You have to create something out of-- you have to make something into existence. That's really hard labor.

I think that desire to suddenly clean the floor or organize yourselves is about anxiety and about avoidance. What I've done is I've really, again, wrapped my arms around it, just like with fear, I say, "Okay. I'm going to feel this way, and I'm going to really get calm and try to override that feeling and get to work." Maybe your mantra should be, "Get started, get started," and really maybe use some mindfulness practices in advance to not allow yourself to get sidetracked. Because if you get sidetracked all the time, you'll never get started. I think that's a really powerful thing to learn how to kind of control those impulses that really are about fear.

Julia: Totally.

Brian: Go ahead. You had a quick follow-up?

Julia: No. I was just going to say anxiety is not a new beast to me, and it's just probably so right on that it's another iteration of that. [laughs] That's really great. I'll put some of my other mindfulness practices to my other anxieties towards this, because maybe it's just about fear of getting started. [laughs]

Cheryl: It is. Just get started, because as you probably know-- I know I have the same struggle as you, but what I find is once I do get started, it's so much easier to keep going because there you are. You're already doing that work.

Brian: Thanks, Julia. I hope that's been helpful. Here's one from Twitter, listener asks, "If you are writing, and various tangential subject start to arise, do you keep allowing them to change the structure or try to corral them into an obedient structure, ha ha," and says, "Thanks for your work." That's interesting, we once had famous author on the show who said that she has the structure of a novel in her mind before she sits down. She knows how it ends.

Then other people called up and said, "No. You don't have to do it that way. If that's good for her, great, but you don't have to do it that way. You can just start writing and create your characters, and see where they take you." How do you take this listeners question about tangential subjects, when they start to arise?

Cheryl: Well, first of all, I want to say there is no one right way to write. If you're the kind of person who has to work off its structure, and that's what works for you, that's great. What I do is I follow those tangents. I think that I'm going to tell you that some of my very, very best writing, in fact, I would say most of my best writing has come from following where the work leads. That you begin the work, you'd have an idea of where you want to go, and then things come up. I think it's really important to trust your intuition.

Creativity is so connected to the deepest parts of ourselves, parts of our brains that we don't necessarily even have access to in kind of regular life. Things will be uncovered as you write, connections will reveal themselves as you write. Anyone who knows the Dear Sugar column knows that I'm constantly connecting one story that seems completely different from the question that has been posed to me as Dear Sugar. Almost every month, as I write the Dear Sugar letter, I have to go through this process that that tweet describes, where I find myself on a tangent, and I find my way back.

The work is deep, because I've trusted that intuitive sense that I have, when I'm being creative, so I would say, go with it. Now, of course, at the end of the project, there is a kind of you do need to harness it all and organize it, and say, "Well, this doesn't fit," or, "That doesn't fit, " but in the creative process and the creation stage trust, where the work leads you.

Brian: All right, listener Terry, I hope that helps you with some good advice. It was Margaret Atwood, by the way, for those of you who are saying you're curious, who was it, who said on the show that she knows how her story ends before she sits down to write it, but everybody works differently. All right. We're just about out of time, Cheryl. Quick-fire round, you ready for like a lightning round? Short questions, short answers. Better to write in the morning or evening?

Cheryl: Okay. Whenever you feel that you're the best writer is the best time to write.

Brian: Some people swear by a 52-minute rule. Write for 52 minutes and then break for 17. Others go on for 25 or for five. What's your pace?

Cheryl: Here, again, I think it depends on the day, but I do think it's important to have a goal, a discipline and stick to the plan. Whether it be five minutes or five hours, follow through with what you said you were going to do.

Brian: When should you show someone a draft?

Cheryl: When you've made it as good as you can possibly make it yourself, after having read it over and over, and over again, and revised and revised and revised.

Brian: Last one, what's a good prompt for when you're stuck?

Cheryl: Right about when you knew it was over.

Brian: Great one, and you know what? That's how we know it's over, so we leave it there, with Cheryl Strayed, bestselling author of Wild, Tiny Beautiful Things, and Brave Enough and known on Substack now as Dear Sugar. Thank you so much for joining us. This was great.

Cheryl: Brian, it's always wonderful to talk to you. Thank you for having me on the show.

Brian: Brian Lehrer on WNYC, more to come.

 

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