“Writing is hard for every last one of us… Coal mining is harder,” Cheryl Strayed told an aspiring writer in her no-nonsense advice on faith and humility. But there is an enthralling ease — or willingness, perhaps — with which Strayed herself digs into the impenetrable surfaces of things and mines the raw material with which to warm our souls, be it in her celebrated Dear Sugar advice column or in Wild: From Lost to Found on the Pacific Crest Trail (public library), her magnificent memoir of mourning and self-redemption in the wilderness, which rose to such levels of cultural resonance as to become a major movie starring Reese Witherspoon as Strayed.
On the fantastic Longform podcast — a belated but befitting addition to these favorite podcasts for a fuller life — Strayed dives into the depths of her writing process, her credos and how she channeled them as Sugar, and the singular and quite possibly unrepeatable-in-our-time experience that precipitated Wild. Her immensely vitalizing conversation with Longform founder Max Linsky emanates the very personhood from which Strayed’s enchanting prose springs.
A necessary note here: We live in a culture that expects us to cushion a conversation with a phenomenal person with the apologetic caveat that it’s two hours long but it’s brilliant and well worth it — a tragic symptom of our shortcuttism. As I’ve lamented elsewhere — incidentally, in a long conversation — real conversations (much like a good book, which requires the same investment and rewards with the same intimacy of insight) are among the few ways to invite meaningful ideas into our lives, for we don’t arrive at meaning via sound bites and status updates. Lest we forget, William James was right — conversation is how “bound energies are let loose.” True thinking — the kind of deliberate reflection that welcomes wisdom — takes time. Digging past the surface of things — getting to what Strayed herself calls “the subterranean river” of truth and meaning — takes time. Time alone may not be a sufficient condition, for the conquest of meaning also requires thought and wholeheartedness and resolute intentionality, but it’s an absolutely necessary one.
Which is all to say, let’s begin to reclaim our humanity by reclaiming our language, which both reflects and shapes our thought. Let’s revert to the lucid conjunction: When it comes to communing with a shimmering mind, the conversation is long and therefore it’s brilliant and well worth it. And so: This conversation with Strayed is indeed brilliant and deeply rewarding in its totality. Below, I’ve transcribed some of the most shimmering parts.
On the latent recognition of how our seemingly unremarkable experiences add up to our becoming, something Strayed addressed beautifully as Sugar:
Some of the most interesting experiences, maybe all of them … become more interesting in retrospect, in hindsight. You know everything that happened and how it came to be.
On good books being the product of processing life’s raw material at its rawest and how that transmutation of sorrow into story into solace fueled her Dear Sugar column:
All of my life has been a processing… Having to forgive and cry and understand mortality and love … you have to do this, I think, to write a book.
We can’t essentially escape who it is that we are, and I am — for better or worse — a writer who likes to go into that subterranean, emotional world and to talk about the mysterious and dark and beautiful places inside of us… I always felt that story was the greatest consolation in my own sorrow, so when I started to help people in their sorrows and their confusions, I had to tell stories.
[In Dear Sugar] I might have told a story about myself, but it was really about the letter-writer — it was really about how can that story illuminate a truth that is universal, not just for me, not just for letter-writer, but for [the readers]. That column was like doing therapy in the town square.
On the misconception that her Dear Sugar column was about giving answers to others, while it was really about showing up for the questions throbbing in her own self and, in doing so, providing the sort of assurance that brings others closer to their own answers:
Ultimately, the truth is that we have to help ourselves — we all benefit from people helping us, but we will never get anywhere if we don’t help ourselves… [There is a] universal truth that we are all are responsible for our lives — that we all suffer and we all need to find light in that darkness, strength in that weakness.
It’s not as if I’m some sort of font of wisdom and perfection — what I’m speaking to is my own struggle. I’m talking to myself, too — all the time, every day. It’s not as if I have the answer and I’m giving the answers. I’m, instead, really down there in the struggle, speaking to it, trying to speak as openly as possible about what it means to be human.
On how great art transcends its creator and speaks to our own lives in the universal voice:
When we see a painting that we love, we’re not standing there thinking about the artist who made it — we’re thinking about how that painting makes us feel, what that reflects to us about our lives and the world. And so I love when love exceeds … its creator, which is the whole goal of art…; when it becomes not about the person who created it, but about the people who consume it…
This is especially true in memoir, where you’re writing about yourself — it has this horrible, false reputation of being the narcissistic form, which I think is pure bullshit. No good memoir is really about the writer — and yet it’s deeply about the writer.
On the three main narratives undergirding any good memoir — common threads of the universal language that illuminate the commonality between Strayed’s memoir, a form predicated on introspection, and her advice column, predicated on empathic outrospection:
If we go back to the ancients, those three narratives are there — they’re in the first writing that we have: It’s about sorrow, it’s about redemption, it’s about journey — the hero’s journey… When I teach writing, I always tell my students: “You might think you’re writing about your divorce, or your infertility, or whatever it is — remember the ancients, because nobody wants to read your book about your little tale.” Nobody should read my book because I took an interesting hike and I loved my mom a lot and she died. That’s just a very small, insignificant story — insignificant to anyone but me. And so my job, as a writer, was to make it about other people…
That’s the writer’s work — it’s consciousness. It doesn’t happen by accident that you learn how to use your life as material for art — this is what we talk about when we talk about having to really apprentice yourself to the craft of writing.
When you’re speaking in the truest, most intimate voice about your life, you are speaking with the universal voice.
On the great leap into the unknown that writing requires, the intuitive flow of which should still be tempered — as Ray Bradbury famously believed — by the intelligent discernment gained only through deliberate practice of the craft:
I’ve been a serious writer since I was nineteen or twenty, and I would say that the difference between being a writer now in my forties versus being a writer in my twenties is that I have just learned how to trust the mystery of the writing process… The most important thing that I’ve learned to trust is that I don’t know where I’m going to land, and it’s okay — but to follow the path where it leads me… I trust that there’s some intuitive place within me that’s driving me forward.
So you trust the intuition, but there is this point in the writing process where you damned well better know what you’re doing — you damned well better know the connection… The intuition falls away — you trust the intuition to get to that place you need to go as a writer, but then it’s not just, like, “Oh, I don’t know how it’s connected — I just know it is,” this kind of, “It sounds poetic, so it must mean something.” That never has worked for me — I’ve always had to eventually say, “No, this is the bridge.”
On the necessary capacity for duality, the complex relationship between our minds and our bodies, and the well-meaning but wholly misguided and infuriating cultural narrative that one should only “think positive” in order for positive outcomes to occur:
My mom was forty-five and she had a terminal diagnosis — she died seven weeks to the day after she was diagnosed… She wanted to live — and she didn’t. And she didn’t have any power over that… For a long time, I was very angry … at this very prevalent idea that we could conquer these terminal diseases with positive thinking — because, the fact of the matter is, sometimes people just get sick and die. And sometimes you just have to live with that fact, no matter what you want.
[And yet] you have to be a positive thinker — you really do have to control your mind in some way and think “I can” instead of “I can’t.” But I think that the danger of saying that is always [the question of] will this be misinterpreted [and] taken to its extreme [of believing that] you can actually reverse course on something like a terminal diagnosis with positive thinking…
If I had to say, in one fell swoop, what is Sugar, what is Sugar trying to espouse, it’s that two things can be true at once — even opposing truths. It could be true that you will suffer forever because you were sexually abused as a child — it can also be true that you can overcome that and not let that experience define your life. And you can hold those two truths in two hands, and walk forward.
I think it’s the same way with the positive thinking — you can’t necessarily think your way out of lung cancer, but you can have a happier life if you think positively in the face of profound sorrow.
On how she applied this dynamic duality to her own life when her memoir became a movie and she was played by the gorgeous Reese Witherspoon, which called for a real discipline in not succumbing to self-comparisons and resisting the tyranny* of perfectionism:
It can be, sometimes, really hard to rise at the most beautiful moments of our lives… I decided that I was going to try to shine, in a sort of Hollywood way — I was going to wear those pretty dresses and get my hair and makeup done and not feel out of place in that world, but I was also going to be who I am and be the size that I am and have the body I have and be the forty-six-year-old that I am, and not allow myself to feel bad about it.
So I did … this mind-control thing, where every single time I thought [something negative about myself], I said, “Don’t think that — you’re not allowed to think that.” And it’s amazing what that can do — when you actually don’t let yourself be mean to yourself… You’re saying, “There you are — I see you, I acknowledge your presence, and you will not rule me.”
And I think that is so essential to any kind of success. We’re all flawed, we’re going to fail, we’re all going to be afraid sometimes, we’re all going to feel terrible about ourselves sometimes, or regret what we did or said… But you have to say, “Well, who is going to be my ruler?” — almost on a moment-by-moment basis.
On growing up poor and being a struggling writer until only recently, then being plunged into a very different world after the staggering success of Wild and learning to reconcile her lifelong values with the realities of her new life as she raises her kids:
[My kids are] going to have to learn what my struggle taught me about the world — they’re going to have to learn that another way. And that’s the thing — I think you can… You can learn as much from your privilege as you can from our oppression, but only if you’re aware of it and only if you have consciousness.
On our mythology of success, which once again bespeaks our difficulty with holding duality:
Every day of my life since the crazy-ass shit happened with Wild, I am fully aware that this is crazy-ass shit. Now, this doesn’t mean that I don’t think I worked my fucking hiney off to have that success — I did. I actually worked my ass off. I also know that it would be true that I worked my ass off if nobody read Wild… The hard work is what’s true — the crazy-ass shit is … just the luck of life, the great fortune of life.
The distinction I’m trying to make here is that there’s a long history of women saying, “Well, I just got lucky.” I didn’t just get lucky — I worked my fucking ass off, and then I got lucky. And if I hadn’t worked my ass off, I wouldn’t have gotten lucky — so you have to do the work, you always have to do the work. And part of the work is about getting comfortable being uncomfortable, learning how to say, “Hello, fear, thank you for being here, because you are my indication that I’m doing what I need to do.”
On learning to dance with the fear and the inevitable self-doubt which, as John Steinbeck’s diary so grippingly attests, bedevils even the greatest of writers:
The way it feels to write a book is that you can’t write a book.
Complement with Strayed’s advice to aspiring writers and her reflections, by way of Adrienne Rich and Marie Curie, on what power really means.
You can — and should — subscribe to the Longform podcast here.
* No era was more tyrannical in its unwillingness to hold paradox than the Victorian, which arguably cemented not only our superficial beauty standards but also our inability to live with duality. A mere century and a half before Strayed, another woman genius was constantly tormented by the pressure to choose between poetry and mathematics. But it was ultimately the fusion of the two that made Ada Lovelace the world’s first computer programmer. Even so, she wasn’t spared the era’s tyrannical resistance to duality — Lovelace, unlike Strayed, didn’t engage with the era’s ideals of ladyhood, leading her contemporaries to describe her as “poetical in appearance,” which was euphemism for unkempt and badly dressed, and only one step removed from “writerly in appearance.”