The Whimsical Guide to Writing Well
A practical and emotional guide to writing in the age of LLMs—we traverse the 9 circles of AI slop hell to remember why we write and how we might recover our true voices.
If the question is, “Why do you write?”
Then our answer is this:
When you are a writer you are effectively a translator of sense—of vision, of experience, of the visceral, of the sublime—and so I write to listen closely to life so that I may capture what it is saying faithfully, and make it legible to others: its immediacy, its force, its unflinching horror, its insistent beauty.
Also this:
To understand who we are. I write to make sense of the nature we’ve inherited and the nurture we’ve learned—to surface the stories we have carried within us all along.
What we’re saying, in many words, is this: anyone alive with words has the capacity to be a writer. She who perceives, he who feels—both are writers.
In past posts, we’ve described a disorientation of sense at the hands of large language models. Our helper bots can rearrange words, giving you a menu of ways to express the same thing; speak in metaphor decently well, though often too cloyingly; and drop bars that have all of the trappings of beauty, and yet are not beautiful.
But our bots do not write, or speak, or mean. They mimic symbolic patterns, convert those patterns into phonemic ones, and produce something that “means” something only in the sense that it has semantic meaning. Now, we’re not linguistic philosophers (though one of us is descended from one), but we posit that semiotics—or the study of meaning-making—has to do not only with the arrangement of symbols and their dissemination in context, but also with the consciousness (or lack thereof) of the messenger. To convey meaning is at once a practical act and a metaphysical one. The uncanny valley is boundless. No matter how advanced the models become, they will always remain just that: models. Representations. Replicas. Forgeries. Frauds.
When we reach for an LLM to anesthetize our fear of the blank page, we bypass the disquieting uncertainty that makes writing truly meaningful. As Flannery O’Connor wrote: “I write because I don’t know what I think until I read what I say.” Joan Didion came to a similar conclusion: “I write entirely to find out what I'm thinking, what I'm looking at, what I see and what it means.” This process of discovery and distillation requires the writer to metabolize the world slowly: to release heuristics and falsehoods and clichés and half-truths; to regard the order of things with receptive curiosity and reverent attention; to arrive, finally, at something true. Writing is a form of thinking as well as self-making: in the pits of ambiguity, and in the misfires of off-kilter sentences, we discover what we want to say, and in turn who we are.
But it’s not an entirely solitary activity: to communicate is a social act, driven by our instinctive drive to be heard and known by others. Good writing will offer, “Here is how I see the world…does it speak that way to you, too?” And it will offer this communion across time and space, as writers are always speaking to their invisible friends, to you, and to me, and to someone yet to come.
If we let machines speak for us as proxies before we’ve found our own voice, we risk not only truth, but also love.
AI creep
You’ve likely noticed an insidious style of writing begin to creep over the internet like an invasive species. It’s benign enough to ignore, you think—easy to read, good enough considering the efficiency gain. We at Whimsy HQ are no strangers to a good LinkedIn hate-scroll (doom-scrolling = endlessly scrolling through vacuous or negative information, symptoms: dissociation, despair; hate-scrolling = endlessly scrolling through garbage or provocative information, symptoms: anger, also despair). The posts on our feeds come from profiles that represent real humans—maybe even real humans pasting their GPT’s output into the text-box—but there is no mind, only machine.
We often send each other marked-up screenshots of AI language slop—not to mock the humans posting it but to mourn the graveyard of fully fledged ideas: post after post of voiceless, viral content, provocative theses neatly outlined with emoji bullet points that garner an endless stream of likes and comments in unspoken praise of the LLMs that wrote them. People share the post, but no sharing actually happens. It’s a holographic feast that leaves you nauseated and starving.
It’s only towards the end of the hate-scroll that we notice the sadder thing, the loosening grip—the surrender. We’d rather hide behind LLMs than reveal our true thoughts, take cover under words that fit the formula for viral growth than risk having our own words fall flat on engagement metrics. After all, if AI represents the promise of super-intelligence, do we then represent the embarrassment of sub-intelligence? Every time we scroll, we imagine ourselves hacking through the invasive plant’s thick and gnarled branches trying to clear the way back to reality.
In honor of our journey through the thicket, we’re here to map the perils. (Note: this doubles as a drinking game.)
Our 9 Circles of Written Hell™
Buzzword Bingo (this one’s a layup).
To quote Mama Virginia Woolf: “Words do not live in dictionaries, they live in the mind.” And I promise you—“paradigm shifts” do not live in my mind. Is your startup idea really “unprecedented”? “Future-proof”? And while we’re on the subject, when you ask us to differentiate between a 10x founder and a 100x founder, are we still on a linear scale? Perhaps the next decade begs for the i5x founder, since the whole thing's imagined anyhow.
The Overwrought Antithesis.
“It’s not X, it’s Y.”
“The real question isn’t if ___, but how ___.”
“This isn’t just about ___, it’s about ___.”
Or, bonus example including the ubiquitous question-answer structure: “The risk? Minimal. The reward? Massive.” (Show! Don’t tell us the answers!)
Look for them—once you see them, you can’t unsee them.
The Alliterative 3s!
“Speed, scale, stability.” “Code, context, capability.”
Growth, grit, guacamole. Leverage, liquidity, linguini.
This is your brain on ChatGPT.Anaphora Inferno
Repetition is powerful.
Repetition is persuasive.
Repetition is predictable.
“The Adverb Is Not Your Friend.” (Stephen King)
An example is best:
She gently touched his arm and softly whispered, “It’s going to be okay,” while he nervously glanced around the room. The wind howled eerily outside as the candle flickered weakly on the desk. He slowly touched his keyboard, tepidly erasing the adverbial letters “L,” “Y.”
versus
She touched his arm. “It’s going to be okay,” she said. He glanced around the room. The candle flickered on the table. Outside, the wind howled. He touched his keyboard and erased the adverbial letters “L,” “Y.”
Binary Bait
You’re either building AI—or getting replaced by it.
Ship fast or die trying.
You’re either part of the solution or part of the problem.I wonder, if we introduced an “and” to sentences like these, how much more interesting the internet might be…
You’re building AI and getting replaced by it.
Ship fast and die trying.
You’re part of the solution and part of the problem (relatable).
The Hollow Hedge
Even as they confidently assert brazen hallucinations as well-researched facts, our large language models are apparently also not too sure of themselves and just want us to like them! Somewhere along the way, they picked up a manufactured politeness—probably from junior women asking for raises (we, too, were trained), perhaps in an attempt to pass the Turing Test.
Common examples: “Just something to think about….” or “It’s kind of amazing how we do this…” I particularly like “A bit of a shift is happening” and am curious how one distinguishes the shift from the bit of the shift.The Prophetic Catchphrase
“The future is here.”
“That’s the thing about X—it’s Y.” For example: “That’s the thing about time—it always runs out.”
If it belongs on Home Goods wall art, it doesn’t belong in your prose.
The Em-Dash Witch Hunt!
Before you come for my precious, beloved, unassailable em dash—that wonderful embodiment of the stream of consciousness—as the telltale signature of ChatGPT, consider all of the above. How the em-dash—which, speaking of semiotics, is a legitimate symbolic representation of a break in a thought like this one—became the single scapegoat, we do not know, and we are here to come to its defense.
Take Emily Dickinson’s “Crumbling is not an instant’s Act” (not only for its lovely use of the em-dash, a punctuation mark she loved and used liberally, but also for its warning to us in our time…). Here is the last stanza:Ruin is formal — Devil's work
Consecutive and slow —
Fail in an instant, no man did
Slipping — is Crashe's law —The em-dash after “slipping” enacts the slip — one slip — and then another. The poem ends at this last slip—crashes as promised by the penultimate word. It seems abrupt until you realize that the em-dashes carried you there. Crumbling is not an instant’s act. It is the result of one too many slips.
TLDR: it’s not the em-dash’s fault!!! God, even our accusations of what makes writing unoriginal aren’t original. Think bigger, people. Leave the em-dash alone.
New Rules on the Block
We’ve returned from hell and brought the em-dash back with us. To restore the ground beneath our feet, let’s come back to what good writing should feel like. Because LLMs are trained on all of the good writing rules, you’ll notice that a few of these rules are now worth breaking. We’re also not saying we’re experts, so we’ve borrowed a few principles from the greats. And before you say “this is only applicable to fiction, why would I use this for work?”—just pause, take a breath, think about it…
Play with structure. Try flipping the narrative arc, or starting in the middle. Let form follow feeling. “All style is, is the awkwardness of a writer in stating a fact,” Hemingway once said, so if the sentence feels awkward, instead of criticizing it, let it be a signal that you’re on your way to saying something. Then edit it. Then edit it again. Then leave it when it feels like it’s awkward in just the same way that you so delightfully are.
Let the rhythm stutter, as one might in conversation. Try overlapping thoughts, or interrupting yourself. Pull a Virginia Woolf and just write long sentences given relief only by semicolons—or take em-dashes for a spin.
Give resolution a rest! Leave the question unanswered, let your readers bask in the tension of silence…
Write badly, for yourself. Then edit. Then remember your reader. Hemingway again, “The first draft of anything is shit.”
But also: “When you first start to write you get all the kick and the reader gets none, but after you learn to work it’s your object to convey everything to the reader so that he remembers it not as a story he had read but something that happened to himself.”Don’t wait to be inspired. As a callback to the beginning of our piece, “She who perceives, he who feels—both are writers.” So, hate to break it to you, but you are indeed a writer. And writers don’t get to wait until they are decidedly “in the mood” to put thought to paper. From Octavia Butler: “The second [rule] is to write, every day, whether you like it or not. Screw inspiration.”
Use whatever medium gets the words out. Moleskin, Notes app, your favorite Speech-to-Text provider—we’re not so stodgy as to say that writing must start with a pen and paper (even if it hurts). The form can evolve as long as the thinking persists.
LLMs are (sometimes—mostly not—but sometimes) okay. AI editors can be helpful for proofreading or editing grammar after the fact—that is if you’re not intentionally trying to break away from grammatical convention. For the process of writing itself, we think it’s best used as negative space against which to define yourself. Maybe you have a couple of stray thoughts you want to stitch together, and you ask ChatGPT to help out. Resist the temptation to accept what it feeds you. Respond to it, resist it, wrestle with it: is that really what you mean—really, really? Listen closely for your own voice—we bet it’s telling you what you really want to say.
“Keep human!” wrote Henry Miller, “See people, go places, drink if you feel like it.” Stories are alive in the world around us—look up and breathe in. Even your LinkedIn post will be better for it.
Pay close attention. Tell us about what your protagonist is holding—not “fruit,” but the dusty skin of a peach, thumb-split and half-bloomed in the Southern heat. Not “depression,” but “the way the eye of a tornado must feel, moving dully along in the middle of the surrounding hullabaloo” (Plath). Not “anxiety,” but “the cousin visiting from out-of-town depression felt obligated to bring to the party” (Benaim).
Conceal strategically. The details that matter, matter. The details that don’t, don’t. “Description begins in the writer’s imagination,” Stephen King reminds us, “but should finish in the reader’s.”
Be patient. Good writing takes time. Just as knowing yourself takes time. Take your thoughts out on a date, and let your drafts teach you. They will reveal, gradually, the truth. Writing is not an instant’s act, either.
For more pointers, see the Marginalian’s summary of Zadie Smith’s 10 rules of writing, Kurt Vonnegut’s 8 guidelines for a great story, David Ogilvy’s 10 no-bullshit tips, Henry Miller’s 11 commandments, Jack Kerouac’s 30 beliefs and techniques, John Steinbeck’s 6 pointers, Neil Gaiman’s 8 rules, Margaret Atwood’s 10 practical tips, and Susan Sontag’s synthesized learnings.
Here’s to blank pages, and happy endings.
P.S. If you ever feel like you can never quite capture the truth of what you see, or how you feel, know that you’re not alone. Here’s a poem, and a prayer, for those moments. To remind you that yes, it’s impossible, and yes, it’s urgent to try anyway.
Epilogue
By Robert Lowell
Those blessèd structures, plot and rhyme—
why are they no help to me now
I want to make
something imagined, not recalled?
I hear the noise of my own voice:
The painter’s vision is not a lens,
it trembles to caress the light.
But sometimes everything I write
with the threadbare art of my eye
seems a snapshot,
lurid, rapid, garish, grouped,
heightened from life,
yet paralyzed by fact.
All’s misalliance.
Yet why not say what happened?
Pray for the grace of accuracy
Vermeer gave to the sun’s illumination
stealing like the tide across a map
to his girl solid with yearning.
We are poor passing facts,
warned by that to give
each figure in the photograph
his living name.
You are such great writers! I learned a lot from reading this piece.
If is a coincidence or a metaphysical manifestation that the publication on my birthday is about a topic I value? Unsure! It is, regardless, a gift! Thank you 🫶🏾