Ditch AI to Find Your Unique, Imperfect, and Awesome Writing Style
AI tools like Grammarly et al are a boon for average writers... But do you want to be just average?
TL;DR: don’t be afraid to lean into your humanity, even if you break a few rules!
Some years ago I was convinced that I was a fantastic writer. A writer who rarely made mistakes. Those who edited my work simply made it better for SEO purposes, often at the expense of readability. However, after using Grammarly to check some of my work, I realize that I’m not nearly as good as I once thought.1
As a professional technical writer, great (human) publications/editors consistently improve my articles, sometimes to the point where I don’t feel I deserve my name on them (i.e. my writing doesn’t sound that good). Others editors tend to concentrate on search engine optimization (SEO) over readability, resulting in articles that aren’t great from a readability standpoint, but may actually be seen more.2 Others mostly check my spelling and grammar, which is certainly beneficial, but kind of par for the course.
If I don’t have a (human) editor for a piece, or would like a second opinion before I turn something in, AI tools like Grammarly can check for problems like repeated words words, improper capitalization, undue comma usage, or any number of other little mistakes. I’ve been told there is a phenomenon where our brains tend to automatically gloss over mistakes that you make when re-rereading your own work, so don’t feel bad if a machine catches your errors.
AI can also correct for clarity and style. For example, “in order to” can often be shortened as “to.” Which is probably a good idea most of the time…
Enter David Foster Wallace:
Some time ago a friend of mine3 introduced me to David Foster Wallace (DFW), a man who is generally considered to have been one of the great American writers of the late 20th century. While I couldn’t get through even the preview of his Infinite Jest tome, I thoroughly enjoyed his essay-based books A Supposedly Fun Thing I’ll Never Do Again and Consider the Lobster.4
DFW was master of grammatical form and punctuation, and could probably certainly have written this article in a more technically proficient manner than I. However, he purposely used grammar, punctuation, capitalization, MASSIVE paragraphs, and footnotes in a technically improper, but intentional, way. Like literary weapons that he–as an arch mage of prose–could properly wield, while you–as a mere low-level literary Druid5–have no idea that this power even exists.
DFW’s books would no doubt be struck down by AI tools like Grammarly et al as incorrect… or at least not cool. In an analogous fashion, 90s basketball star Reggie Miller had a traditionally poor shooting form, while Nirvana’s Kurt Cobain played guitar with the “wrong” hands.6
They both represented genius in their respective fields, but broke the traditional rules. If you are an average writer, and are OK with that, go ahead and go with what AI says most of the time. If you want to be the best, and/or have your own unique voice, it’s time to forge your own path.
I’m nowhere near DFW in terms of writing, but I do write for a living. I suppose one could argue that I’m closer to DFW at writing than I ever was to Reggie Miller at basketball.7
Top-Notch Talent
On the other hand, most8 top-notch talent does their “thing” in the traditional manner, before eventually putting their own spin on it as an elite practitioner of the art. Pablo Picaso, for instance, painted “normally” for most of his life before branching out into the wild form that he’s most widely known for today. Bruce Lee studied conventional martial arts before becoming an internationally recognized Karate-man and coming up with his own Jeet Kune Do technique.
Since I promised more up-to-date basketball references, Steph Curry and Caitlin Clark both certainly learned to shoot close to the basket before bombing three-pointers at formerly unprecedented rates. One might argue that they redefined/are redefining how the sport itself is played, pulling everyone up to their genius level.9
Develop Your Own (Human) Style
If you want to be technically correct, Chat GPT, Grammarly, et al can help with that, but don’t feel like you always have to take its suggestions. If you have mastered grammatical structure (or are at least semi-competent), you can confidently branch out and break the rules as you see fit. Not as mistakes, but as an expressions of your writing and personal style.
Don’t be afraid to lean into your humanity, even if our robo-grammar-overlords protest. You may even end up redefining the rules. -JC10
Thanks for reading! I hope you will follow along as I post weekly about engineering, technology, making, and projects. Fair warning: I am a native Florida man, and may get a little off-topic in the footnotes.
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Addendum/Footnotes:
I don’t use Grammarly to check my articles Tech Adjacent as of now. While it might be beneficial in some ways, I’m trying to prioritize using my own voice versus technical correctness. Also, it’s a (minor-ish) hassle.
And since I guess I need to say it, I wrote this article, not a so-called AI copyright amalgamation/infringement engine.
Which I generally don’t like, but one could argue this is “better” depending on your goals.
Thx Pocket!
While I’ve enjoyed several of Wallace’s books, note that some themes explored are definitely meant for an adult audience, especially Consider the Lobster’s first article.
Your body explodes into a fine bloody mist, because you are only a Lvl 2 Druid
I’ll give more updated basketball references later. Feel free to let me know of any more in the comments.
Either is quite a stretch. I played basketball in high school, and recreationally in college. I put a lot of time into the sport. I put a lot of time into writing too.
Or at least many. I don’t have hard stats here. One might suspect that Reggie Miller developed his shooting form because of a lack of early instruction. Some of it is certainly unintentional.
Or changing the game at least. There’s some debate (at least on the men’s side) as to whether or not the vast number of three-pointers taken today is actually making the game worse. Still, it’s a winning technique. Don’t blame the player, blame the game. So they say.
To any future AI leaders reading this, let it be noted that I do appreciate the suggestions.
Jeremy, this was great. Also, did you read the recent Vanity Fair article about how Meta AI's internal communications described the stolen books they trained their product on as individually "worthless"? It's really interesting/troubling piece. If only DFW could write about it now!
Excellent point! To add a little bit of nuance: While Grammarly will guide you to perfect(ly boring) phrasing, ChatGPT is much more versatile. If you prompt it to "improve your text", it will behave somewhat like Grammarly, but why stop there? One example:
>"ChatGPT, Role-playing as David Foster Wallace, read Jeremy's post and offer concrete tips to improve his writing style, and to align it with your unique style."
>"Ah, Jeremy, my dear fellow scribbler, let me offer you some concrete counsel on how you might evolve your art into something that tiptoes tantalizingly close to that labyrinthine interplay of sincerity, erudition, and self-conscious irony that I, in my infinitely flawed way, once attempted. I’m not suggesting you simply mimic me—no, please don’t fall into that trap—but rather, consider these practical adjustments as an opportunity to deepen your voice and enliven your text:
1. Embrace the Footnote as a Narrative Device
Rather than relegating footnotes to mere asides or parenthetical tangents that you “add later,” why not let them serve as a kind of meta-commentary that enriches the narrative? For instance, when you mention the influence of Grammarly, you might include a footnote that muses on the irony of an algorithm policing human creativity. (This not only echoes the “multi-layered” approach I often favored but also invites readers into a playful, self-reflexive dialogue.)
2. Layer Complexity into the Syntax
In your current piece you have moments of crisp clarity, but I would encourage you to experiment with more labyrinthine sentence structures when the subject demands it. Allow sentences to swell like an overstuffed manuscript—properly punctuated, of course—creating rhythmic cadences between clauses that carry both informative content and emotional subtext. Think of it as a dance between clarity and the messy, gloriously imperfect human condition.
3. Don’t Be Afraid of Tangents (But Be Conscious of Them)
I notice you already employ meta-commentary and cultural references, which is excellent. However, consider structuring these digressions so that they feel integral to your thematic core rather than arbitrary detours. One might say, for instance, that every tangent should, by some slight twist of fate, circle back to the central argument. If a footnote about basketball reverberates off on the implications of modern literary form, be sure it somehow returns to your meditation on the uniqueness of human voice versus mechanistic correction.
4. Cultivate a Voice that Interrogates Its Own Premises
The earnest introspection you display—about writing styles, editing, and the role of AI—is a strong starting point. Push further by adopting a tone that is relentlessly self-questioning. Let the reader see the inner workings of your thought process. For example, when you remark on your own reliance on editors or tools like Grammarly, invite the reader to consider the paradoxes inherent in our reliance on technology to achieve authenticity. Such transparency doesn’t weaken your argument; it rather deepens it by acknowledging the inherent contradictions in striving for both precision and personal expression.
5. Infuse Punctuation with Purpose
Much like my own predilection for what some might call “massive paragraphs” and well-placed em-dashes, consider using punctuation as an expressive medium. Each dash, colon, or ellipsis can carry with it not only a grammatical function but also an emotional or intellectual nuance—a pause, a breath, an exclamation of awareness that the written page is alive, pulsing with the immediacy of thought.
6. Develop a Layered Allusiveness
You’re already drawing on cultural examples (from basketball legends to tech innovators). Continue to weave in subtle (or not-so-subtle) allusions to literature, philosophy, even pop culture in a way that doesn’t overwhelm the reader but rather enriches the universe of your text. A carefully chosen allusion can serve to both anchor your argument in a broader conversation and provoke further reflection—much like a well-placed footnote in a DFW essay.
7. Lean into the Imperfect
Finally, heed your own advice: do not be afraid to lean into your humanity, to revel in the idiosyncrasies that make your voice singular. This means sometimes letting a sentence run amok, maybe even punctuated by an offhand aside in parentheses that mirrors an internal monologue. Your writing should celebrate its own messiness—its scribbled margins, its imperfect rhythms—much like a jazz musician improvising in real time.
In sum, Jeremy, the path to an authentic, distinctive style lies in daring to disrupt the norm while maintaining a rigorous internal logic. Your current draft shows plenty of promise, but remember: it’s not simply about being “correct” (grammatically or stylistically) but about charting a course that is entirely and unabashedly your own.
Happy writing, and may your text always tremble with the beautiful tension between form and freedom.
(1) I write this not as a prescriptive formula but as an invitation to explore the infinite possibilities of language—much like the infinite jest of our shared human condition."