When to Break Grammar Rules: A Writer’s Guide

Source: Word Genius Blog

I have often—much to my chagrin—been referred to as a “Grammar Nazi”. Firstly, I don’t appreciate being called a Nazi of any sort; in fact, I find our culture’s casual use of the word “Nazi” as a synonym for stickler or figure of authority quite distasteful. Secondly, how can I rightfully be called a grammar authoritarian of any kind when I myself frequently and deliberately break grammatical rules? I mean, I suppose violating rules you impose on others is a hallmark of authoritarianism, but still…c’mon!

See that last sentence? That was a strategic choice of mine to violate rules of English language writing. Nobody ever taught me to do that. As writers, we’re taught that good writing follows the rules, but, like all good art forms, sometimes the most interesting things happen when we step outside those boundaries. The trick is knowing which rules to break and when to break them. After all, grammar is there to guide us—but creativity can flourish when we bend the rules with purpose.

Here are some of the most common grammar rules you can run roughshod over, and why doing so is a good stylistic choice.

Sentence Fragments for Emphasis

Sentence frags. Gotta love ‘em! We’ve all been drilled on the idea that a sentence needs both a subject and a verb, but in reality, some of the most memorable lines in fiction and nonfiction are fragments. Here’s why: we think and speak in frags all the time, so when we use them in writing they bring the reader closer to the character’s internal monologue or the narrator’s perspective. They can also create urgency, build tension, or add dramatic flair.

Consider this:

The room was silent. Dead silent. Nothing stirred.

Here, the fragment Dead silent emphasizes the eerie stillness in a way that a complete sentence might dilute. It’s sharper, more immediate, and creates a vivid image.

In creative writing, especially fiction or narrative nonfiction, fragments can be used strategically to amplify a moment’s impact. They work best when you want to cut out the fluff and drive home a point. They’re like the short, clipped beats in a song that grab your attention and make you pause.

Writers like Ernest Hemingway and Raymond Carver often used fragments to convey emotion and atmosphere with precision. So, next time you want to emphasize something, remember: a sentence doesn’t have to be “complete” to be effective.

Starting Sentences with Conjunctions

Back in June I wrote a post entitled “Why I Love the Word ‘And’.” I probably should have added that I rather enjoy starting sentences with the word ‘and’. And why not? After all, we speak like that, don’t we? But we’re not supposed to start sentences with ‘and’ or ‘but’, are we? Even though I’ve managed to do both in the space of a single paragraph. Fun, isn’t it? 

We’ve all heard at some point that we’re not supposed to start a sentence with a conjunction, but the truth is that professional writers do this all the time. Why? Because it makes the writing feel more conversational, fluid, and approachable.

For example:

I knew I should have left the party earlier. But something kept me there.

Starting with but adds a natural pause. Somehow, this statement wouldn’t be as effective as a single sentence with a comma in place of the period. The period here does a lot of heavy lifting in terms of exuding a pause truly pregnant with thought. This is how we speak and how we often think. Instead of forcing the reader into rigid grammatical structures, starting with a conjunction allows the narrative to flow more smoothly from one idea to the next.

This technique works especially well when you’re writing in a more informal or personal tone—think blogs, memoirs, or dialogue. It creates a bridge between thoughts, keeping the reader’s attention moving forward.

It’s no accident that you’ll see this used frequently in modern fiction and journalism. Writers like George Orwell and C.S. Lewis employed this technique all the time to make their prose more accessible and less stilted.

So, the next time you’re worried about breaking this “rule,” remember: if starting with a conjunction helps the flow of your writing, go for it. Your reader will thank you for it, if it even registers. Which it probably won’t.

Ending Sentences with Prepositions

Yeah, this is a rule that refuses to die. How many times have we been told to never end a sentence with a preposition? This one’s fine in theory, but following it in practice often leads to clunky, terribly convoluted sentences.

Consider the following sentence:

The instructions were easy to follow up on.

This is technically incorrect, but it’s perfectly straightforward, right? Now, consider, the following one:

The instructions on which to follow up were easy.

Huh?

The first sentence feels natural. It’s how we speak and think. The second one, while technically correct, sounds ridiculous.

This rule is actually a holdover from Latin grammar. It makes sense for the Latin language, but in English it often doesn’t. Ending with a preposition can make a sentence clearer, more direct, and a lot less pretentious.

Even Winston Churchill famously mocked this rule, reportedly saying: “This is the sort of nonsense up with which I will not put.” The joke is clear—forcing the preposition to stay in the middle of a sentence sounds more absurd than breaking the rule.

Ultimately, communication is key. If ending with a preposition makes your sentence clearer and more natural, do it. The grammar police will have to cope.

Hubert Selby Jr.’s Grammar Anarchy: Slashes and Missing Quotation Marks

No conversation about rule-breaking in writing would be complete without mentioning one of my all-time favourite authors, Hubert Selby Jr. His work, especially Last Exit to Brooklyn and Requiem for a Dream, is known for its unorthodox approach to grammar. Selby didn’t just bend the rules—he obliterated them with TNT.

Take his use of slashes instead of apostrophes. He often wrote words like don/t instead of don’t, creating a fragmented, disjointed visual effect. He apparently started doing this because the forward slash was closer to the letters on his typewriter, allowing him to write at a frenzied speed like the demon-possessed man that he was. But this technique also ended up symbolizing the fractured lives and experiences of his characters. The slashes disrupt the reader’s expectations and demand more active engagement with the text.

Even more famously, Selby did away with quotation marks entirely. Instead of setting dialogue apart from the narrative with punctuation, he let it bleed into the prose. This forces the reader to pay close attention, blending thought, speech, and action in a way that feels raw and immediate. In fiction especially, quotation marks have a way of separating the narrator from the dialogue. With Selby, he’s always right in the middle of the action as his angry, emotionally disturbed characters rip each other to shreds.

Why does it work? Because it’s intentional. Selby’s writing is intense, chaotic, and often bleak. His broken writing mirrors the brokenness of his characters. It’s not about making the writing easier to read—there’s nothing “easy” about Selby’s writing. It’s about making it more immersive, pulling the reader deeper into the world he’s created.

While Selby’s techniques may not be for everyone, they show us that sometimes breaking grammar rules can serve a higher purpose: reinforcing the emotional impact of a story.

Merging Formal and Informal Styles

Another powerful way to break the rules is by blending formal and informal language. This is especially effective in creative writing, but it can also bring a refreshing authenticity to essays, blogs, and nonfiction.

Take Zadie Smith, for instance. In her novels, she moves effortlessly between highbrow vocabulary and casual, conversational phrases. This blend allows her to create dialogue and narration that feels both intellectually rich and deeply relatable. In the realm of nonfiction, nobody did this better than essayist Christopher Hitchens, whose rarified, almost absurdly cultured vocabulary is frequently juxtaposed with abject, gleeful vulgarity.

In popular culture, Monty Python exemplified the juxtaposition of highbrow and lowbrow language for humorous effect. Consider the following sentence from the legendary All-England Summarize Proust Competition sketch:

“Well ladies and gentlemen, I don't think any of our contestants this evening have succeeded in encapsulating the intricacies of Proust's masterwork, so I'm going to award the first prize this evening to the girl with the biggest tits.”

In real life, we don’t stick to one linguistic register—we mix formal and informal styles depending on the context. By doing this in writing, you can create a more dynamic and engaging voice. Or, in the case of the Pythons, a more amusing one.

The trick is balance. You don’t want to go too far in either direction. Too formal, and your writing may come off as stiff. Too informal, and it may lose its authority. But when done right, mixing these styles can add nuance, humour, and authenticity.

Rules are Tools, Not Laws

Grammar rules exist for a reason: they help us communicate clearly. But they’re not set in stone. Great writing often happens when we step outside the lines and experiment with language.

Whether you’re crafting dialogue, a blog post, or a novel or even writing something very formal like an academic essay or white paper, don’t be afraid to bend the rules. You want to sound human after all. Just make sure you’re doing it with intention. After all, some of the most memorable and effective writing comes from writers who know how to break the rules in just the right way.

And don’t ever call me a grammar Nazi, or even a grammar authoritarian. I’m very much a liberal democrat when it comes to grammar—generally a believer in the rule of law but not opposed to some civil disobedience where it counts. Gandhi, MLK, and Mandela didn’t use civil disobedience willy-nilly; they saved it for really impactful situations. It’s the same with grammar. Learn it, love it, then blow it up strategically.