Cheryl Strayed: How To Become A Writer & Advice Every Creative Needs To Hear

Hey, it’s Marie Forleo and you are watching MarieTV, the place to be to create a business and life you love. Today you are in for such a treat because we have one of my favorite writers of all time on the show.

Cheryl Strayed is the author of the number one New York Times bestseller Wild, Tiny Beautiful Things, Brave Enough, and Torch. Her books have been translated into 40 languages. Wild was the first selection for Oprah’s Book Club 2.0 and made into an Oscar nominated film. Cheryl’s essays have been published in The Best American Essays, the New York Times, The Washington Post Magazine, Vogue, Salon, The Sun, Tin House, and elsewhere. She’s the co-host of the Dear Sugar radio podcast and lives in Portland, Oregon.

Cheryl, thank you so much for being here.
Thank you for having me, I’m thrilled.

Yes. So when we met at Super Soul Sessions, I was just…

Oprah introduced us.

Yes, which is a big deal.

Yeah, it’s a nice start for us.

And I knew having you on MarieTV was going to be just exciting. So let’s take it back, way back. You didn’t grow up in a household of writers.

No, I didn’t.

How early did you know that you wanted to be a writer?

Very early. I mean, soon after I learned how to read, when I was about six. I… you know, I fell in love with books, but in particular I had one experience that I read this one book, it was a chapbook of little poems. There were watercolor pictures. It was the 70s and so everyone was into these little sort of watercolor chapbooks. And each little poem described one aspect of the beauty of nature. And I remember very distinctly it was the first epiphany of my life that I just was so struck, so pierced, truly, by the beauty that somebody could create simply by words on the page. You know, I appreciated those pictures, but it was the words that transported me. And, you know, it was one of those very early ideas. I certainly at that point didn’t think, “This means I want to be a writer.” But as I grew up and became a writer I very much remember that as the moment that I became aware of this thing that I can only describe as a calling.

Did you ever think to yourself, like in your teenage years, oh, I could potentially do another career? Or was something in your heart always writer?

You know, what I thought is that I absolutely had to do another career. When I was growing up, I didn’t have any idea that I could actually make a living off of writing books and I don’t know exactly how to explain that except to say that even though I loved literature, I felt that the people who made those books were people who were so distant from who I was. Many of them, you know, many of those books that I was assigned in high school, just like you, you know, they were by dead white men, essentially. They were created somewhere in a land, in a time far off. And so I never imagined that I would grow up and be able to make my living that way. It was always the thing I would do because I was called to do it, because I was passionate about doing it. And then I would earn my living in some other way. And I remember when I was in high school I was always a feminist and I was one of, you know, I subscribed to Ms. magazine. And I remember at one point reading this story that was about Joyce Carol Oates and I was so struck by it because I was like, wow, there’s a woman, she’s living among us, and she’s writing books. I’d never heard of Joyce Carol Oates, but I was fascinated by this profile of her. And it was the first glimmer of an idea that I had maybe I could be a writer. And then when I went to college and started to take English classes and some of my professors were teachers and authors and, you know, and really they opened that door for me of possibility.

Isn’t that interesting? That I think for all of us and for so many women too, it’s like we need to see someone do it.

Absolutely. Modeling, right? I mean, I think that’s why, you know, it was so powerful when Barack Obama was elected president. We suddenly all became aware of, you know, not only the historic moment of that, but what that would mean to children of color all over the world to see him become the president. And, you know, I think the same thing with Hillary Clinton. I think that those things are really powerful in big and small ways. I mean, you know, I’m not being hyperbolic when I say that I didn’t… I couldn’t imagine what was possible until I could see that somebody else had done it.

Let’s talk about the realities of making a living writing. So many people in our audience are creatives, they’re aspiring creatives. Whether it is writing books or painting or starting their own business. Take me back. How did you earn a living in the early days? What were you doing?

I did a bunch of different things. So I… really when I graduated from college I was a double major in English, creative writing, and women’s studies. And I knew that I wanted to dedicate myself to writing. I knew that this was going to be a years long apprenticeship. It wasn’t something… I never bought into this false notion that, like, I’ll just sit down and, you know, spend the next 6 months writing a book and then that’s, you know, then I’ll be done. I knew that it was going to be a long slog. And so I decided to try to find work that would support me in my writing rather than contradict those goals. And for me that was becoming a waitress, because it was a job that I could walk in, do the work, and do honest work, but not take it home with me. You know? And I knew that I feared that if I got a job, you know, that was in some ways fulfilling, like I’d also worked as a newspaper reporter for a brief time in college and I loved it. And I was writing and, you know, so I was sort of filling that need but I wasn’t doing the real work that I wanted to do. So I avoided sort of that work in my field, if you will, for a good… the better part of a decade. And then, you know, I tired of waiting tables. It made me feel diminished and sad. But, you know, it was a great way to earn a living for a while. And I would write when I wasn’t waiting tables and I would go back to work. But then I thought, you know, I need to do some more meaningful work. And I did a number of different things. I started, you know, teaching writing because I’d started to publish a little bit. I started also writing pieces for magazines because it was a way in some ways to begin to feel like I was a real writer to get published. One of the early decisions I made was to not focus on getting published, but to rather focus on my craft, which I think was a very wise one. But there did come a time that it was time to start reaching out.

I think that that’s such an important distinction. So many people are in such a rush to monetize whatever the thing is that they are truly passionate about, that they feel is their art. And I don’t think that I’ve ever heard anyone articulate, you know, I deliberately held back and wanted to work on my craft. And how did that feel for you? Was it exciting to be able to just say I’m not gonna pressure myself to get this out into the world?

Well, you know, so much about creative work and certainly about writing is, you know, the way you survive is by, you know, running along at the speed of your own engine. It’s not going to be because somebody from out here validated you. Like, it really… writing is very much generated from within. I think any kind of art making or any kind of creative work, you have to ultimately be doing it because you feel driven to do it, you feel passionate about doing it. You… you’re engaged with something that feels important to you in your life. And certainly in the arts what I can say is if what you’re going to rely on is that exterior validation, you’re just not gonna… you’re not going to get it. You’re not gonna last long. And so, you know, that decision was about learning, really learning how to keep faith with my vision or my dream or my work. And then, you know, once that became like actually that inner strength is what I drew on to compel me every day forward through another day of trying to write something that meant something to someone else, you know, once I really developed that muscle within then when I did go into the world and people said nice things about my work, it was thrilling, it was beautiful, but it wasn’t the thing that made me keep writing. And I think, you know, you’re so right about this. I teach writing sometimes, or I certainly talk to a lot of people on airplanes and so forth. How do I write a book? You know, what’s your advice? And the advice is always kind of depressing to people because the absolute only advice I really truly have for somebody who wants a life as a writer is write. Write. And keep writing, and keep writing and see what happens. It’s not about, like, go to this party or go to this conference. And those things come up along the way. Like, I do think at a certain point it’s important to start to meet people, meet your tribe, meet people who are doing what you’re doing, put yourself out there. I think the most important thing is to learn how to make a home with the work that you’re doing, because then you have something to offer the world. You know, a lot of people want to make that offering before they’ve created anything.

Yeah. Let’s talk about your rituals because I’m always fascinated by people who create any kind of art, but especially writers. Do you and had you developed a practice of writing every day? I’ve also read you binge write.

I’m a binge writer. I’m not an every day writer.

Not an every… ok, so this is all so fascinating. There’s a book that I love called The War of Art by Steven Pressfield and several other books. And some people that I know and they’re great writers, they do, they have this discipline, they write every day. So I’m curious, yeah. Tell me about your binge writing.

Yeah. It’s really interesting because for a long time I thought I’m a renegade. I’m a bad writer. I’m not a real writer because I’m not doing this thing that many times, you know, this is the advice that writers are given.

Yeah.

If you don’t write every day or most days, that means you’re not a writer. And that’s… if that’s true, I’m not a writer then. You know? And what I can say to you is what’s to me really important is, I use this phrase before, keeping the faith, which to me is connected to discipline. To say what really is meaningful for me, the work that’s meaningful for me, is writing. And so I’m gonna find a way to do it. And for some people that… what works for them is every day.

Yeah.

Very… there are certain stretches of my life, times in my life, where that’s what I did. You know, there were many times for 3 months in a row I wrote every day. But there are also many times for 3 months in a row I didn’t write a word. And what I’ve found is when, like, I make an appointment with myself and I don’t look at each day. I look at the calendar ahead. And it’s been really helpful for me actually also to decide when not to write, because I can look sometimes at my calendar and say, “I’m gonna be really busy for the next month,” or, “I just gave birth to a child,” or, you know, I have to work really hard at this other project because that’s important to me too. And then I just put the writing aside and know that I’m not going to feel bad about it, I’m not gonna get into some sort of shame loop about I haven’t written. I tell myself you’re not going to write now and then you’re going to write then. And then what I do is I make good on that promise. That’s the other piece of it. This isn’t about being, you know, using lazy excuses. It’s not using this methodology in order to not write. It’s actually the opposite. It’s saying this is when I work best or when I can work best. One of the most moving experiences I had, you know, I give so many talks about my books, usually about Wild or Tiny Beautiful Things that, you know, the Dear Sugar column, and so often people, the response they have to that is about the stories they tell me about their own losses or their own struggles or how the book helped them in one way or another. But I will say, one of the most moving comments I got after one of my talks is just during the Q&A afterwards. Somebody had asked me what my writing process was and I said about this binge writing.

Yeah.

And I said, you know, I don’t write every day and sometimes I write once a month. And this woman came up to me afterwards and she said, she was crying, and she said, “Thank you so much.” She said, “I have always felt like I wasn’t a writer. I’m a single mom, I have 4 kids, and I can write once a month, the day my mom takes my kids. And I think you’re the first person who told me that I can still say that I’m a writer even though I only write once a month.” And I just grabbed her and I was like, “You are absolutely a writer. Because if you write once a month, guess what happens by the end of that year? You’ve written 12 days. And I know you can do a lot of beauty in 12 days. Because I’ve done it too.”

It’s a relief for me. I’m one of those people, my audience knows this, I put a tremendous amount of pressure on myself, and that is the writing every day thing. You can start to hear, I can hear the voices in my own head. Like, you’re not really one. Or I’ve even beat myself up over this one. I wrote a book years ago but I haven’t written one in a while, but I write and produce this show and I can sometimes hear the voices in my head going, “Oh, I’m not a real writer because I’m not writing books like everyone else is.” So I will echo that woman’s thank you for that. And I know there are thousands of people watching this right now who are also thanking you for that.

You know, it’s interesting to me, this idea what happens when we’re gentle with ourselves. Like, that voice that you just talked about in your own head, it’s… that’s about shame.

Yeah.

That’s about… do you work well from a position of shame?

Absolutely not.

I don’t think anyone does. But what about, you know, I think sometimes we have associated gentleness or tenderness with a kind of slack or kind of letting you off the hook.

Yes.

And actually what I’ve found is only just when I’m gentle with myself can I actually really let go and do the work. To say, ok, it’s been hard to sit down at the computer. I’m gonna forgive myself and move forward now. And it’s not about shame, it’s about forgiveness, it’s about gentleness. I think that’s really important when you think about a creative endeavor. And that goes back to this idea I said about how… if you are the engine, you know, of your own dreams, if you are the only one who’s really gonna propel you forward down the path in those ways. Because you are. Like, nobody’s going to come to you and say please make a show, please write a book, please make a song or do a dance for us, or paint a painting for us. Nobody’s… especially at the beginning. You know, nobody for years did that for either of us.

Right.

Right? And so you have to find, you know, you have to find that way to do it yourself. And so maybe in some ways what I sort of subconsciously did is like, you know, how do I give myself the gift of that? And one thing I realized early on is I have to let shame out of my life. Like, I cannot make shame part of my writing life.

So powerful. So you’ve said, which is a perfect way to follow up with this conversation, “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.”

That’s right. So much of writing, I mean, I love… the reason that that metaphor came to me is that I think of writing, the word I use all the time is excavation. And it feels like a literal excavating to me, you know, we begin with the empty computer screen or the empty page and we are creating something out of absolutely nothing. You know, even if you’re writing nonfiction, even if you’re writing about your life or something that happened or something you know or think, you know, you’re creating something out of nothing. And almost always that process entails then, you know, going beneath what you thought you were going to write, and then beneath it again. And then you show it to somebody to read and they say, “Well, what’s this about?” and then you have to dig. When I teach writing I make this… I put on this butcher paper in front of the room what I call kind of my literary lasagna. And it’s like, you know, up here is the, you know, the top layer, the lovely cheese. And then… so you’re looking at it, a lasagna sideways, and you have to get all the way down to that bottom layer to really do your work.

So speaking of your teaching, I noticed there are two questions that you pose to all of your writing students, and I think that these questions are incredibly important for all creatives. Would you like me to read them?

Yes.

Ok, great. So what’s the question at the core of your work and what question are you trying to answer for others?

Yeah, that’s right. Because I think especially… this is true in fiction too, but it’s literally true when you’re writing about your own life or your own experiences is that, you know, I think we almost always begin out of that place like that thing that we’re seeking for ourselves.

Yeah.

And when you write memoir, when people talk about memoir in negative terms, it’s almost always that they say it’s the form of narcissists. Like, who would be interested in you? Who would be interested in my childhood? And the answer to that is, kind of, nobody. And the artist’s job is to make it interesting. And the ways that we make that interesting is that you can read about my childhood and see your own in it, even if it’s totally different. You know, even if you came from a different place or lived in a different time or, you know, inhabit a very different reality. And I think that that’s what I’m always striving for as a writer and a teacher when I say, you know, what is that personal question at the core of your work and how does that translate to the culture? And, you know, just an example I can give you, in Wild, for years it’s my memoir, it’s about my hike on the Pacific Crest Trail. But it’s also very deeply about my grief. I went to hike that trail because I honestly didn’t know how to live without my mother. I really felt I couldn’t live without my mother. And I think that all those years later when I wrote the book, I was still there. I was like I was still wondering, how do I live without my mother? How do I live without my mother? Asking that over and over again. And what I realized in the course of writing Wild, and actually what compelled me to write Wild, is by examining that question in my own life in a memoir, what I was really examining is how is it that we live with our losses? How do we bear the unbearable? How do we endure our suffering? Because, you know, one thing I know about that is we do and also we all do. You know, and so right there that translation goes from me and my loss about my mom, which is a very particular and individual thing, and I’m going to tell you a story about it. But what I hope to tell, what I hope to tell really in that telling of that story is that larger, you know, universal struggle that we all have about how we figure out how to bear our losses.

And I also want to thank you for this because I still have my mom… I’m gonna totally cry.

You’re making my cry looking at you.

I just love her so much and your work has given me, like, an even deeper appreciation for the time I have with her, so thank you for that.

Yeah. That’s one of my favorite things, people telling me, you know, people who have living parents say, “You know, I finished your book and I called my mom and I said thank you.” And let me tell you, there’s also an entire tribe out there of people who don’t have their moms. They either don’t have them because they died or they don’t have them because they lost them to drug addiction or mental illness or incarceration. And those people come to me and feel recognized in the work too. You know, that has meant more to me than, you know, all of the glorious, glamorous things that have happened in response to that book.

And I think that’s the beauty of art and that’s the beauty of words and that’s the beauty of vulnerability and sharing what is in your heart with others. So thank you for that.

Thank you. The power, too.

Yeah.

I mean, beauty and power. When we… when we say that art has power, that’s what we mean. We mean your tears right now.

Yeah. I wanna talk about something that you mentioned at your Super Soul Session, which is the paralyzing pressure that we can often put on ourselves to do something great.

Right.
Especially when it comes to writing or our art or our businesses. And how there was that time when you were in Massachusetts where it was almost you couldn’t do it.

Yeah.

You’d said…

I was paralyzed by my own dream!

Yes. Can you talk to that?

Yeah. It’s really… so much of the interesting stuff in life I think, you know, there’s so much contradiction inherent. On one hand I want to say, you know, dream big. You know, aim high. I’m an incredibly ambitious person and I always have been. You know, I was the person, I said in that talk, I was the kid at 5 who’s like, no, I’m going to be the first woman president. You know, I’m gonna just, like, always go for… I’m gonna reach really, really hard and really high. But there came… which I think is wonderful. I mean, it is in part what brought me here, Marie. It’s how I got here with you today. Right? That ambition. It also was the thing that I had to turn away from for a time of my life and I’ve learned periodically to turn away from it. I’m in a different moment of my life that I’ll explain in a moment. That I also have to turn away from this ambitious side. And that is to say, you know, when I was sitting there in Massachusetts at my little cottage in Massachusetts trying to write my first book, I suddenly felt like I can’t do this. And what that was about is realizing I can’t sit here and make greatness. What I can sit here and do is write one page and then another page and then another page. And I don’t really know what those pages are going to be in the world beyond me, and maybe they’ll be nothing. And for me today to have to surrender this vision of me being, like, the great American novelist was painful, but it’s the thing that allowed me to actually write my book. You know? It was… I realized I had to set aside those big dreams and those ambitions and all those things I’d internalized and be humble and to just say I’m gonna do my best. I don’t know if anyone will like it and it’s absolutely none of my business if they do. I mean, it’s just like I’ll do my best and I’m just gonna say, “Here’s my best, world.” You know, take it or not. And that’s what we always are doing. I mean, we think… we like to think otherwise. That’s about like, you know, thinking that we can always control the outcome of everything, but we don’t really know. You know? When I was writing Wild, I had no idea that it was going to become a best seller. I wouldn’t have written it any differently. You know? I wrote the same book I would have written if it were still in my drawer right now at home. Ok? And so I think that’s a really important thing to remember. And when I said earlier about how I’m kind of in this moment now in my life.

Yes.

Here I am for the first time writing a book that people are, like, waiting for. You know? When I wrote Wild I had published a novel, I had a nice little fan base, but it wasn’t like there was some great clamor like, “When’s your next book?” You know? And now I do have that, that feeling of people being present in my mind as I write. And I’ve had to just let it go. I’ve had to say I don’t know if this next book is going to be as good as Wild. I don’t know if people are gonna love it. But the only thing I can do is write page after page after page. One of my favorite quotes by Margaret Atwood, whose writing I love, she says, “A word after a word after a word after a word is power.” And I always try to remember that. That my work, my job in trying to create power, is just putting one word after another word after another word.

I want to shift to the after-Wild success. And I want to talk about something that I don’t know if a lot of folks picked up or they may not have seen your follow-up interview with Oprah where you shared that Wild had just come out, filmed the interview with Oprah. So many people have this idea or this notion that if it’s Oprah or, you know, some other television show, they have you on and all of a sudden financially you’re a big success and everything is ok, but that wasn’t the case. Tell us about what your life was like in that.

Yeah. It was… it was really one of the strangest experiences of my life. The entire process of what happened with Wild, when it first was published in March of 2012 right out of the gate the first week it was out it was number 7 on the New York Times bestseller list. And I distinctly remember getting the call from my editor that my book had made the New York Times bestseller list. And I just thought this is the mountaintop. You know? Like, I have reached… I had not even really dared to imagine that. You know? I wanted that but I was like I’m not going to define myself by that kind of that measure of success. I’m going to define success in other ways. This is all true. I believe this sincerely. But it’s also true that that was a really beautiful moment. And I thought that it was the peak of what was going to happen. But of course what happened is things kept going and going and then Oprah called and I went on the Oprah show and, you know, the book sold and then the movie came out and all of those great things. But you’re right, you know, that what happened along the way in addition to that success is that my life changed. I went from being this, you know, essentially the classic starving artist who had two little kids, my husband is a documentary filmmaker and we were living hand to mouth. And during that transition time when I was, you know, in the world as this incredibly public success, I was also home and broke. The month that Wild came out and was on that list, our rent check bounced. And my husband texted me, I was on my book tour, and my husband texted me and said the rent check bounced. Why did it bounce? And I texted him back because we don’t have any money. And we were so sad and alone because, I mean, we laughed about it too. He called me then, I remember that we were saying to each other nobody knows this but us. And part of that… and, I mean, that’s part of the reason I talk about it.

Yes.

Because part of that, you know, we have… we have really, I think, bad ideas about money as a culture. You know, we flaunt wealth, but we don’t speak realistically about what money is or what, you know, especially in a, you know, the creative arts. It’s like what does it… what do you expect? You know, what’s realistic? It’s like this big secret that we want to keep from each other because it’s impolite to talk honestly about money. And so I think it’s important to just, you know, I’m proud to say, ok, yeah. There was this time that I looked really successful to the outside world, but I was very much still struggling financially. And one of the most interesting things happened during that time. Another writer who’s very successful, I won’t name her because just in case she doesn’t want to be outed, who I’d never met got in touch with me and she said… and I hadn’t shared any of this stuff with her. She just saw that Wild was a success. And she said, “Let me guess. Everywhere you go with all of your friends they expect you to pick up the tab because they’ve all decided you’re rich. But you don’t have any money. Your credit cards are maxed out.” And I was like I love you forever and ever. Because I could sort of talk to her about that in that moment. And so there was this real collision between, you know, who the world perceived me as in that moment and what was really happening in my life.

And you’ve also shared, you know, the writing life doesn’t move in a straight line.

That’s right.

And that no matter how many successes, and even though we do have some successes, rejection still comes.

Yeah. Well, and I mean, I think this is always true. I’ve never… I’ve met so many successful people. I’m friends with so many successful people. And you know, one thing really pretty much across the board, no matter how grateful you are for your success, how astonished you are that you had such good fortune, there’s always something that you want that you didn’t get. Some award you were passed over for, some project that you undertook, you know, after your success that was a failure or rejected or not as well received as other things. You know, it’s really… it isn’t a straight line. I mean, not just in the creative arts. I mean, I think in all of life that’s true. And I think that’s actually a positive thing rather than a negative thing. Can you imagine how awful we’d be at the end of our lives if it was all just, like, an upward trajectory?

It’d get so boring and we would never grow.

That’s right. I mean, so much of growth… really, this is the other thing. Having met so many successful people, especially in these last 4 or 5 years, I always ask people about their stories, their origin stories. And really what they tell you about along the way are the things that they failed at, the lessons they learned the hard way. And those things really deeply contribute to our success. I believe that absolutely. There’s no way around that because they are the things that we remember. They are the things that give us the opportunity to rethink, to alter our course, to be humble. You know, I think that that humility is such a core piece of being able to succeed, which really runs contrary to, I think, the American view of what, you know, how do you achieve success? You’re this arrogant blowhard, I won’t name names. And that’s, you know, you’re the boss. You own the room. Or even as we say, you’re the man. You know? Which is, you know, I think a really false idea of what success looks like.

I agree with you 100%. I’m shifting us to, you know, I love all of your books but Brave Enough, your quotes…

Thank you.

So many I have clearly marked. I want to read you one, but this is one that we love on our team and I think everyone loves it as well. “Nobody’s going to do your life for you. You have to do it for yourself. Whether you’re rich or poor, out of money or raking it in, the beneficiary of ridiculous fortune or terrible injustice. And you have to do it, no matter what is true, no matter what is hard, no matter what is unjust, sad, sucky things have befallen you. Self-pity is a dead end road. You make the choice to drive down it. It’s up to you to decide to stay parked there or to turn around and drive out.”

That’s right. That’s right. And I think it’s ok to drive down those dead end roads sometimes. What’s not ok is getting stuck there. You know, I think that because the only person you’re harming with staying in that mode of self pity is yourself. You know. There’s absolutely, you know, we are responsible for our lives, as I said. I mean, I’ll just, like, paraphrase the quote.

Yeah.

And I think I learned that in so many different ways over the course of my life. How… why does that quote resonate for you?

I think because I’ve always grown up feeling like I’ve gotta take care of myself. And there is a beautiful side to that, which is self-reliant. And I think the underbelly of it, for me at least as an individual, is always resistance to ask for help. But there’s something about that just really owning no one’s gonna do it for you. And I think it’s a good message for all of us to hear that we can pull ourselves up by our bootstraps and make things happen. I also wanted to shift into, you know, as Dear Sugar, you field thousands and thousands of questions. And it’s part of what we do here on MarieTV. We have thousands of questions that people write into us. One of the themes that we notice that people write in about is this fear of making the wrong decision, whether it’s in their careers or it’s in their relationships. So much of what you’ve talked about you’ve learned because something bad has happened. Can you speak to that, the power of not worrying about whether or not you’re making the right decision?
Right. You know, I think most of us, we want to stay safe and we want to stay comfortable, and this is why we stay in jobs that we don’t really like. Because it’s like, oh, this is the reasonable thing to do. Or we stay in relationships that aren’t serving us or good for us anymore. Or maybe never were. We stay in friendships or relationships with people who are destructive to us. You know, and it’s… and I think that the root of that is about fear and is about having to experience that kind of pain or discomfort that happens right after you make that move, you end that relationship, you quit that job. And everyone around you is saying, “Why did you do that? He seemed like a great guy. Well, what are you gonna do for a living now? How are you gonna pay the rent?” All of those questions that you get in those rocky periods after we actually shake things up. You know, I think many of us sort of innately recoil from them. And what I’ve learned is, you know, basically there’s no way around that. The other option is to stay in the thing that sucks.

Yes.

And then what happens? Then you… then you look up and it’s like, you know, you have a life of regret, you have a life of I wish I would have done this 10 years ago. I can’t tell you how many middle aged and older people are in my writing workshops who say to me I always wanted to be a writer. I always wanted to be a writer, but I… but it was… it didn’t… it wasn’t… it didn’t make sense. And they never… it haunted them all their lives. And then they’re finally in my workshop and they have a sense of regret. All those years they could’ve been doing what they loved. And, you know, this, it’s also true that, you know, I grew up working class and poor. I’ve spent most of my adult life really having to figure out in a deep way how to pay that next bill. Until, you know, recent times, that’s been a reality for me. So I don’t say this from a position of, like, don’t worry. Just go be a painter and you can, you know, somebody will pay your bills. That’s not what i’m advocating. It’s a very fine point. When I say you have to make your own life, you do have to figure out, as I say in one of my Dear Sugar columns, you have to pay your own electric bill. You have to figure those things out. You know, there are practical ways that you can build all of that into your life, you know, nurturing your creative soul while also putting it together to pay the rent. I’m not just speaking from that place of privilege.

I think one of the other things that’s so utterly endearing about your Dear Sugar columns is how you’ve managed to embrace these extremely difficult situations and give people perspective and advice, so to speak. It just walks this line of duality that two things can be true at once. Something can be extraordinarily annihilating to our souls and we can still get up and move forward.

Absolutely. I think almost always two things are true at once. Right? You know, I mean, I think about all of the best things in my life, every single best thing in my life is also incredibly hard. You know? It’s incredible. I mean, being a mother, being a wife, being a writer. You know, all of those things, they entail so much. You know, there’s… it’s not all, like, joy and rainbows and unicorns. Yeah. And so I think about that too, you know, like what I just said, ok, so follow your dreams and live out that vision that you have for yourself even if it is gonna be hard to earn money doing it. And also, oh, you’ve got to earn money. You know, that it’s not one or the other. I think really when we try to find, like, carry both of those truths, you know, in both hands, that’s almost always when I think we feel the most actualized. I’ve been thinking lately about, like, what is happiness? You know, what is the definition of happiness in my life? And for me it’s really very much that my… that what I appear to be in my exterior life is very close to who I really am inside. You know, the joining of, like, that I’m not pretending. That I can say, you know, what really makes me excited as a creative person is writing and that I’m somebody who does write. You know, it’s… it’s such a tragedy when you have… when you meet those people in the class, “Oh, I wanted to write for 30 years and didn’t until now.” And they look at me with such loss in their eyes. Or that marriage or that job, whatever it is that makes people feel that they have to pretend rather than live out who they are inside. I think that that is a far deeper suffering than any sort of difficulty that might be felt when we make that leap.

So I want to go to a quote that you have that speaks to the power of us revisiting our own narrative, something that I feel like I need to do more of. And I think all of us maybe perhaps. “Don’t surrender all of your joy for an idea you used to have about yourself that isn’t true anymore.” Have you been examining your own narrative? I can only imagine that you have with how much has happened in these past few years.

Yeah. It’s an absolute ongoing process. And what a difficult and humbling one. The biggest one for me is most definitely, you know, that I’ve always been a person who leapt into the world and the answer was yes. Everything. I wanted to do everything. I wanted to take every opportunity that came my way. And it was really a part of, you know, part of how I, you know, made it as a writer is, like, always grab every rope that swings by. Grab it and climb up it and see what happens next. And what happened with Wild, and I think this is, you know, it’s partially because of the success of Wild. It’s also partially because of where I am in my life. You know, I’m 48 and I know that so many of my female peers in particular had reached this phase in their lives at this age where you start to say, you know what? I’m not going to say yes to everything. Because part of saying yes to everything was that thing, you know, that I’ve always said can’t be the answer, and that is making other people happy, making… getting my validation from outside. You know, the thing about yes is when you say yes to everyone, everyone’s happy with you, but there did reach a point… there has reached a point lately where I’m like, but I’m not happy with myself. That I need to learn that word no. And this seems like a really small thing. It’s been a real shock of the last few years for me that it’s a very difficult thing for me. I mean, it’s really difficult. It’s like epically… it’s a struggle that goes down to, like, the core of who I am and I am trying to learn how to do it. I’m not… I’ve made some progress and I’m not, like, I’m not on the other side of that. You know? And so I think that that’s, you know, when I say, well, what’s the story I tell myself about, like, who I am in the world? Part of it, I’m trying to in some ways embrace a side of me that is less pleasing to others so that I can protect myself more. And that’s just incredibly hard for me.

No is… it’s a word that for me comes up… I have this little phrase that we teach our B-Schoolers, our online business program, and I talk to them about getting a first class ticket on the no train. Because I remember for myself, yes to everything. And it is part of, especially in the beginning, what helps you climb and develop strength and start to put yourself in the way of amazing opportunities to contribute and grow. But then there does come a certain point where it’s self-preservation. And I think also for me, there’s a dimension of that of pushing against societal definition of success. More isn’t better, bigger isn’t better.

Right.

And so I am with you in that constant reevaluation and really taking my yesses seriously. And the no has to come up and it is, it’s challenging. And part of it for me is I want to support people and I want to contribute and I want to help.

I’ve always… all of those things for me.

And so… and then there’s that part of me when I say no I feel like, gosh, am I being ungrateful? You know, am I being ungenerous? And all those things. So I just think this is a great conversation to have because I’ve met so many women who are also feeling that same way, trying to find that balance of being able to say no to the world so they can say yes to themselves.

Absolutely. And, you know, one thing I always sort of feel a little bit of better… I take comfort in is I think that people who are ungrateful probably never stop and ask themselves, “Am I being ungrateful?”

That’s right.

You know what I mean? Like, just the fact that you’re asking that question, you know, tells me you’re not. And that’s because you have consciousness about gratitude. You have consciousness about helping others and giving back. And I absolutely feel like one of the greatest gifts of the success I’ve had is bringing all of these people along with me and helping and giving voice to people who didn’t have voices or, you know, all of that stuff. Like, I’m… sign me up. You know. But what I realize is I can’t do it all. Because in so many ways, what it will keep me from doing too is the thing that got me here in the first place. You know? Writing those books.

Yes.

And writing does entail saying no to everything but me in a room and the silence.

Yeah. And I do wanna point out, because I researched this about you, that now, because your life is very different. And, you know, writing when we’re in our teens or twenties and we don’t have families and mortgages and pets and husbands and kids, that sometimes you will just take yourself to the Marriott.

That’s right.

Down the street.

The local… like, I’ll go on hotels.com, like what’s the cheapest hotel within, like, a mile of my house and just check into a hotel and spend a night or two writing. Because I am a binge writer. I write best when I can write in, like, 14 hour stretches. And so I do that. You know, I’ll also escape sometimes, I have a cabin now up on Mount Hood in Oregon, it’s like an hour from my house, escape to the woods to write. You know, and those are really important things. Silence, it’s never become more difficult to get that because of the beautiful world of the internet and so forth. But I think it’s really a valuable thing to reach for.

Yeah. And I actually think, if I can make a prediction, I think within the next 5 or 10 years we’re going to start seeing a lot more places that will be wifi and technology free.

Yeah, I think you’re right.

Little havens for folks to go and just disconnect from…

Yeah, it’s kinda like when real butter went out of fashion for a while. Margaine.

Yeah, and now it’s back.

It’s back.

It’s really back. Ok, two more things before we wrap up. Future dreams. Any future dreams for you?

Yes. Well, there are books I want to write. You know, when I think about my professional life, that’s the most meaningful work for me. And, you know, I’m working on a book right now and then I’ve also started, like, the book after that. And I had to set it aside so I could work on the book I’m writing right now. And they both live within me. They’re like these kind of phantom children that I haven’t yet brought to life. And I really am very deeply invested in carrying those out. And with each book I think, like any writer, I want to learn more and do better and tell a deeper, bigger, more important story about what it means to be human. And so I’m, you know, always endeavoring in that direction. All of my dreams, when it comes to my creative work really, I mean, I do all kinds of things, but it’s really like writing those books that matters the most.

Time in the cabin.

Yeah. It’s really just that I want to go stay at the Marriott. Room service!

That’s right. Let’s wrap with one of your favorite quotes, I believe from your mom. Putting yourself in the way of beauty.

Right.

For anyone watching, if they find themselves, their life circumstances right now are perhaps in frustration or maybe they’re in the midst of a deep loss, how might that quote give them some comfort?

Right. Well, what that quote means is, you know, my mother, who did not have an easy life, who often had reasons to feel stressed out or upset or, you know, even depressed, would say to me and my brother and sister when we were complaining about anything, “This is… this is on you.” Life will always present us with challenges. Life will always be difficult. Life will… things will always disappoint us or hurt us or make us feel bad, but you don’t have to stay in that feeling. That every day the world at large gives you the opportunity to witness beauty, and so put yourself in the way of it. Put yourself in the way of beauty. There’s always a sunrise, there’s always a sunset. You get to choose to be there for it or not. And that’s been a really important way of thinking about life for me, because, again, it isn’t saying that life is easy. It’s not… I don’t like the quotes that are all about these kind of pie in the sky, everything is beautiful and so let us never sully that. I love beauty that’s grounded in struggle. And that’s what my mother meant about putting yourself in the way of beauty. That life will always be hard and life will also always be beautiful. You know, I think about… I was just last night with a friend whose son died a couple of years ago, his teenage son, and we were talking about, you know, how have you survived this loss that makes you feel like every day you can’t keep living? I mean, I really… that’s what that loss feels like to him every day. And I already knew the answer. I don’t even need to ask it. Because every day something also is beautiful. And it’s right there alongside all of our sorrow and all of our loss and all of our ugliness. And so we… that’s the piece of life that we can control. We can’t control whether your kid dies when he’s 16. Right? But we can control what we do with our days, where we find that light to go on.

Cheryl, you are a national treasure.

Thank you.

Thank you so much for being here. Thank you for your body of work. You’re an incredible human and I adore you. I love you. I look forward to all of the rest of the work that continues to come out of you.

Thank you. It was so lovely to be here. Thank you for having me.

Now Cheryl and I would love to hear from you. We talked about a lot of amazing things today. What’s the single biggest insight that you’re taking away from this conversation? Leave a comment below and let us know.

Now, as always, the best conversations happen after the episode over at MarieForleo.com, so go there and leave a comment now. Once you’re there, be sure to subscribe and become an MF insider. You’ll get instant access to an audio I created called How to Get Anything You Want and you’ll also get some exclusive content, some giveaways, and personal updates from me that I just don’t share anywhere else.

Stay on your game and keep going for your dreams because the world needs that special gift that only you have. Thank you so much for watching and I’ll catch you next time on MarieTV.

I could’ve said things to make you cry so much harder.

Oh my God, you’re such a sweet…

I scaled it back there.

You’re a skilled woman.