Why the Best Writing Advice Is Often the Weirdest

In “Thirty Recommendations for Good Writing Habits,” an essay published in 2013, the writer and translator Lydia Davis offers a cardinal rule: “work on your character.” (She happened on a variation of this maxim, by Stendhal, in her copy of the “New Basics Cookbook.”) Davis is famously precise, and the way she uses “character” has multiple dimensions: it could mean a writer’s habitual gestures and ethical traits, their quirks and turns of phrase. Or it could mean, simply, the character in a story. This is advice that feels like a dare, if not a rebuke: your writing will become interesting only if you spend your days becoming witty and wise. It’s not calculated to put anxious writers’ minds at rest—most of us already live in fear that our flimsy characters will be exposed through our work.Putting words on the page seems too low stakes to get worked up about, and yet the terror of saying something taboo—or just being boring—feels like a terrible fate to most writers. I see this every day as a writing coach, a job I’ve done since 2019, first teaching online classes and now mostly working with students one-on-one over Zoom. My task is to read their unpublished, often unfinished writing—less as a teacher or as an editor than as a cheerfully unlicensed therapist. I ask the writer to read their work aloud. They begin by delivering the words like an embarrassed waiter. About five minutes in, the writer’s voice steadies. They might cry, moved by their own words. They hear the false notes but also the truth of what they’re saying. It’s not “good,” not yet, but it’s a start. I ask questions, look for the story behind the story, and review sentence-level decisions. I watch for moments when the author is having fun.The work is as relational as it is technical: my students almost always solve their own problems by being heard, talking their way into an answer, and gaining the confidence to bat away my bad ideas. I’ve found that coaching works best when the writer is willing to gradually stop relying on me as an authority. As Leslie Dick writes in her 2018 essay “Soft Talk: Thoughts on Critique,” we all wish for someone “who can guarantee and validate our identities and our practices” but “the one who knows doesn’t exist.” That’s good news even as it feels like a loss. When writers stop performing for an imagined judge, the language loosens: the prose becomes more like riffing with a friend than giving a speech, and the unconscious pipes up with its desires and fantasies, some ugly, some dumb, some funny, some profound. All workable.In a talk on the “art of rough drafting,” George Saunders, the Phil Jackson of writing teachers, says he’s learned, through writing and revision, that “there is a mind greater than the one I’m talking to you with right now . . . and it’s smarter than me.” In my coaching sessions, I try to help a writer reach this smarter, intuitive mind. As much as I admire Davis’s exhortations to work on one’s character—and I do return to them—they point toward what an aspiring writer can become someday rather than the move they usually need to make in the moment.In an interview with the website Public Parking, the writer Lucy Ives describes ad-libbing a writing exercise to kill an awkward classroom silence. After leading her students through a couple of bluffed warmup prompts, she asked them to “describe something that they’d completely forgotten.” As she explained, “I wanted it to be impossible to do the exercise ‘correctly.’ ”Ives’s new book, “three six five: prompts, acts, divinations (an inexhaustible compendium for writing),” is built around the premise that an exercise succeeds when there is no right answer. “How to walk backward” begins: “Write a description of your bed after you have slept in it.” Then, a chair you’ve sat in, a room you’ve left, a glass you’ve drunk from, a person you no longer know, a belief you no longer hold; each instruction receding a little further until you’re trying to see “something so far out of sight that it cannot be seen.” I tried this prompt and snagged on my own incomprehension. Knowing Ives’s work, I suspected this was the point. I can’t say I enjoyed the feeling, but I did keep going. I wrote about the worn neck pillow on my unmade bed and my iced coffee in a Bonne Maman jar. It felt dutiful and boring. Then I stopped trying so hard, and the protagonist of my novel came into focus. The exercise concludes: “Turn towards the now-invisible place from whence you came. Wave slowly.” As someone who has tried more than my share of silly writing prompts, I’m annoyed when this kind of thing succeeds—and it did. I wrote a scene I’d been avoiding.“Three six five” continues a project Ives has been pursuing for years. Within a sprawling œuvre—more than a dozen books of poetry, fiction, and essays—the act of writing itself is often the main character. As she put it in a Granta interview: “narratives are always tied to and emerging from other narratives.” Her books resemble metafictional mises en abyme, stories within stories within stories not unlike the mini-narratives that make “three six five” appealing as both a guide and a work of literature in its own right. Since her 2009 début, the poetry chapbook “My Thousand Novel,” she’s taken on, among other things, fake Wikipedia entries, an abecedarian essay, and a #MeToo systems novel, “Life Is Everywhere,” in which the story detours through several texts in the main character’s bag.Ives’s 2019 novel, “Loudermilk: Or, The Real Poet; Or, The Origin of the World,” is set at the Seminars, a backbiting M.F.A. program that is a fictional version of the Iowa Writers’ Workshop—Ives’s alma mater. The book follows Harry, an introverted poet, and Troy Augustus Loudermilk, a handsome blowhard who pretends in workshop that he wrote Harry’s poems. The book is one of the funnier portrayals of a writing program. (A sample line: “Harry is reawakened by the sensation of something stiff and damp prodding his face.” It’s a Sharpie.) But it’s also an earnest inquiry into the social forces behind writing education and the romantic notion of “genius” that sustains it. At one point, Marta Hillary, the Seminars’ star faculty member, describes what writing is to Loudermilk, saying, “We’re here to . . . confront the fact that, as humans, we are fated to make things, and we are, meanwhile, the subjects of history.” We can’t produce words without being subject to the hostile systems that produce us in turn. Loudermilk, of course, misses the point of this monologue.The image from Ives’s body of work that best evokes the feeling of suffering through a draft is one from her 2021 story “The Care Bears Find and Kill God.” The story begins with the narrator battling a fear of flying. She is in the air, listening to a recording of herself reading a PDF she found by Googling “meditation script fear flying.” The script is bad at anticipating her eccentric panic: “I visualized stripy colorless surrounds, wobbling with narrative instability—my body’s collision with the infinite.” Still, she keeps listening. The manically therapeutic clichés (“Panic attacks cannot hurt you! You are free from panic attacks when flying!”) offer scant protection. And yet the plane lands.Writers have a bevy of mantras—“show don’t tell,” “kill your darlings”—that mainly help by giving the writer a sense that there are rules. But the rules can’t govern the place the work comes from. As Dick writes in “Soft Talk,” “Whatever we intended to put out there is exceeded by our unconscious thoughts and wishes, as well as by our social construction as subjects within discourse.” The unconscious doesn’t take direction. I see this show up in coaching sessions as transference: writers project the role of parent, teacher, judge, and executioner onto me, asking for reassurance that their writing is not bad and that they aren’t either. Writing guides wrestle with the contradiction of needing to be the “one who knows” while also tacitly admitting that they can’t possibly make a writer’s crucial decisions for them. The strictest guides—classics like Strunk and White’s “The Elements of Style” or William Zinsser’s “On Writing Well”—sidestep this contradiction by limiting their authority to questions of technique. But technique isn’t where most writers get stuck. Anne Lamott’s “Bird by Bird,” a modern classic and a workshop staple, finds an elegant (possibly unconscious) solution: It appears to be a straight-shooting craft manual—sections include “Getting Started,” “Plot,” “Finding Your Voice”—but the useful tips keep getting swamped by Lamott’s catalogues of writers’ neuroses, including her own. Describing her jealousy when a less talented writer succeeded, Lamott writes, “I was literally oozing unhappiness, like a sump.” It’s as if she is failing strategically so that the reader’s growing disillusionment with her propels them toward self-sufficiency. Her most enduring concept, the idea of a “shitty first draft,” lets other writers know that they, too, can drop their pretensions.Where “Bird by Bird” slyly undercuts the “one who knows,” books like Julia Cameron’s appealingly woo-woo “The Artist’s Way” outsource it to “the Great Creator,” “Higher Power,” “the universe,” or, simply, “God.” Cameron’s 1992 mega-best-seller, a twelve-week recovery program for blocked artists, exemplifies a much-imitated, spiritually inclined self-help approach to the perils of creativity. Adherents range from Elizabeth Gilbert (“without The Artist’s Way there would have been no Eat, Pray, Love”) to Tim Ferriss (“the most cost-effective therapy I’ve ever found”). Many otherwise cynical writers have a grudging allegiance to ​Cameron’s rituals: writing stream-of-consciousness “morning pages” every day, combatting “blurts” (i.e., negative self-talk) with affirmations, and taking oneself out on “artist’s dates.” “Everything about the book is mortifying, and it totally set me free. Its ridiculousness is matched only by its effectiveness,” Meaghan O’Connell wrote in an article in The Cut called “This Terrible Self-Help Book Is Actually Making Me a Better Artist”“Three six five” falls into this lineage, even as it offers a more radical alternative. The book design signals that readers are in for something more expansive and less cringe than “The Artist’s Way.” With its gradient-colored cover—a royal blue that shades into a bright green—dyed page edges, ribbon place markers, and debossed lowercase text, the book resembles a devotional text or a mood ring. Inside, each of the three hundred and sixty-five exercises breathes on its own page. Spindly line drawings by Nick Mauss pop up periodically—surreal figures like a lobster telephone—though they don’t illustrate the text so much as shimmy​ and dream alongside it. The prompts offer tasks ranging from reviewing “an imaginary book,” to repeating a word until it stops making sense. (A punk friend gave Ives this mind-bending idea when she was sixteen.) They are gnomic (“create a circular work”) and ambitious (“write a thirty-page sentence”). If you can pull off that last one, Ives assures us, “you are ready for the big leagues!”The publisher of “three six five,” Siglio, was founded in 2008 to publish unclassifiable text-image hybrids like Ives’s, which draw on the twentieth-century avant-garde. The book’s clearest precursor is Yoko Ono’s Fluxus-coded “Grapefruit,” from 1964, a compendium of conceptual art instructions that includes intentionally nonsensical prompts such as “imagine one thousand suns in the sky at the same time.” Ono’s husband, John Lennon, later acknowledged “Grapefruit” as the inspiration for his song “Imagine,” and said that Ono deserved a co-writing credit (in 2017, she got it). In a 1971 interview, he said, “I think this is an important book to help people act out their madness. If you do some of the things in it, you stop going crazy in a way.”Self-doubt and fear have always made writers feel crazy. The material conditions we work in have become more demoralizing, as authors have less time to reach a more distracted audience for little pay. And yet every day writers call me from conference rooms at their day jobs, or cramped kitchens with their children, or cars sitting in their driveways—sometimes the only place quiet enough to think. Ives gets at what draws writers back to the craft when she observes that “the contemporary era is beset with forces who want to convince us that language can be lossless-ly quantified.” The same forces are at work on the people who use the language. Figuring out what you really think is one way of remembering that you’re human.In the last volume of “In Search of Lost Time,” after more than three thousand pages of autobiographical excavation, Marcel Proust writes that literature is an optical instrument a reader turns on himself. Ives asks the writer to look through the wrong end of the telescope and recognize their own character. My favorite prompt from “three six five,” “weak spot,” turns the turbulence of the writing life into something that, on a good day, feels like a joyride. Ives says to take one of your drafts that isn’t working and “try to write even more intensely in its style.” Failure is a reliable and infinitely renewable resource. Every day, we board the plane. ♦