TL;DR version:

Most grammar rules are either the fault of an eighteenth-century bishop with a Latin fixation, or schooldays scaffolding that never came down. They are not (despite their confident manner) laws of nature. Language changes constantly — always has, always will, largely without anyone’s permission. Every attempt to freeze it in place is a rearguard action that eventually loses, as forty sword-carrying French academics in fancy coats have been discovering since 1635.

In marketing, the only question worth asking about a sentence is whether it works: whether it’s clear, whether it sounds like a human wrote it, and whether it moves the reader forward. The reason people invoke school rules in content meetings is not grammatical principle. It’s that judgement is frightening and rules are somewhere to hide.

This is understandable. It is also, at the precise moment it happens, the moment you’ve stopped thinking about your reader and started thinking about yourself. Which is, for marketing purposes, entirely the wrong way round.

There is a particular moment that happens in content meetings.

Someone has written something. It’s good — clear, human, does what it needs to do. And then someone else reads it and says, with the careful air of a person delivering difficult news:

“You can’t use ‘they’ as a singular. It’s grammatically incorrect.”

Except it isn’t. It never was. It’s been in continuous use in English since at least the fourteenth century¹. Chaucer used it. Shakespeare used it. Jane Austen used it in Northanger Abbey, which is not generally considered grammatically lawless.

The singular “they” is older than a singular “you”. And people never seem to question if that can be both singular and plural².

The rule against it — the confident, categorical, everyone knows this rule — dates from the eighteenth century. A bishop wrote a grammar book³. He had Opinions. The opinions spread. Somewhere along the way they became Law, despite being, in the technical linguistic sense, entirely made up.

This happens more than you’d think.

(While we’re on that topic, have a look at this piece showcasing the evolution of English, and see how far back in time it still make sense.)

A brief and somewhat depressing history of rules

The story of English grammar rules is largely the story of people looking at Latin — a language English is not descended from and does not structurally resemble — and deciding English should (obviously) work the same way.

Latin cannot split an infinitive. The infinitive is one word. You cannot insert anything into a single word without it ceasing to be a word and becoming a mess. English infinitives are two words — to go, to write, to pontificate — and have always been cheerfully splittable. E.g.: to boldly go⁴

This did not stop eighteenth-century grammarians from decreeing that you shouldn’t split them in English, on the basis that you can’t in Latin⁵. Which is a bit like telling people they shouldn’t eat soup with a spoon because chopsticks work differently.

The ban on ending sentences with prepositions? Same era, same logic, same Latin fixation. The King James Bible ends sentences with prepositions throughout⁶. Nobody complained. This was 1611. The rule hadn’t been invented yet.

What we have inherited, in other words, is not a set of eternal truths about language. It’s the opinions of a handful of eighteenth-century grammarians who were very fond of Latin and very confident about everything else.

They were not always right. But they were always Very Sure.

What school did with this

School took these rules and did something understandable with them: it taught them as Facts.

Which makes sense. You have thirty children⁷, a limited amount of time, and a genuine need to establish some shared conventions before anyone can do anything useful. Simplification is necessary. “Don’t start with And, don’t split infinitives, don’t end with a preposition” is a workable scaffold.

The problem is that nobody came back later to dismantle it.

Nobody said: right, you’ve got the basics, now here’s the more interesting part — the part where you learn to judge. Where you work out what a rule is actually doing, and decide whether that’s what you need right now, and bend or break accordingly.

Instead, the scaffold became the building⁸. The training wheels never came off. And people carried these rules into adulthood, into workplaces, into content meetings — still wearing their school uniforms (mostly metaphorically, unless they went to one of the fancy schools that wear suits), slightly bewildered to find themselves there.

The thing nobody says out loud

Here’s what I think is actually going on when someone invokes a school rule in a professional context.

It’s not really about grammar.

It’s about not wanting to be wrong in a way that’s specifically theirs. Rules are psychologically wonderful for exactly this reason: they outsource the decision. If “never start with And” is a law, you don’t have to think about whether this particular And, in this particular sentence, is doing something useful or not. You just don’t. Done. Safe. The rule absorbs the risk.

Judgement, by contrast, is terrifying. Judgement means you can be wrong in a way that belongs to you. You made a call, it didn’t land, and there’s no rulebook to hide behind.

So people reach for rules not because the rules are right, but because rules feel like solid ground in a discipline that is, if you look at it directly, mostly quicksand and educated guessing.

Which is entirely understandable. Also: the moment someone does this in a content review, they have stopped thinking about the reader and started thinking about themselves.

And the moment you stop thinking about the reader⁹, you’re not really doing marketing anymore. You’re doing something that looks like marketing from a distance but is mostly self-protection with a brand logo on it.

What linguists think (and why it matters)

There are two broad camps in linguistics.

Descriptivists believe language simply is however people use it, and the job of a linguist is to observe this rather than police it. Dictionaries, under this view, are not rulebooks but records — snapshots of a living thing that has already moved on by the time you’ve finished writing it down.

The prescriptivist position feels intuitively reasonable. If anything goes, what stops everything dissolving into chaos? How do you teach children to write? How does a contract mean anything? How does anyone know what anyone means?

These are fair questions. They’re also, on closer inspection, not really what descriptivism is arguing. Nobody is suggesting chaos. The descriptivist point is simply that language is not a building that requires defending — it’s a process that’s been running continuously for thousands of years, largely without anyone’s permission, and attempting to freeze it at any particular moment is both futile and, in the meantime, faintly exhausting for everyone who just wants to write a sentence.

The evidence for this is, at this point, fairly overwhelming. Every generation produces new words, new constructions, new idioms that the previous generation insists are wrong. Almost all of them survive anyway.

The people who insist are eventually outnumbered by people who just use the language and get on with things.

A case study in magnificent futility (or magnifique futilité)

If you want to see prescriptivism taken to its logical conclusion, look at France.

The Académie Française was founded in 1635, which makes it older than calculus, the steam engine, and the concept of the sandwich. Its purpose, from the beginning, was to regulate the French language — to identify correct usage, purge undesirable foreign intrusions, and ensure that French remained French in a satisfyingly official way. Bonne chance!

It has forty members, known as les Immortels. They wear embroidered ceremonial coats and carry ornamental swords. There is a waiting list. This is a real institution, doing real things, in the present day of whenever you’re reading this.

For the past several decades, the Académie’s primary battle has been against loanwords. Words like email, weekend, hashtag, and selfie have been officially disapproved of (probably with much tutting) and replaced with sanctioned French alternatives. Email should be courriel. Hashtag should be mot-dièse. Selfie, officially, should be égoportrait.

The French, on the whole, have continued to say email, hashtag, and selfie¹⁰. The Académie has continued to disapprove. Nobody has been arrested. The language has continued to move.

This is not a story about French people being reckless. It’s a story about what happens when an institution confuses its own preferences for the laws of nature. The Académie can declare that égoportrait is the correct word jusqu’à ce que le visage soit bleu. But if the actual humans who speak French don’t use it, it isn’t a word, it’s a wish.

King Cnut famously demonstrated to his courtiers that even un royal cannot hold back the tide. The Académie Française has been re-enacting that demonstration, in metaphorically damp embroidered coats, for nearly four hundred years¹¹.

The lesson for anyone tempted to treat language as something that can be correctly administered: the tide does not read the memo.

The prescriptivist position feels intuitively reasonable. If anything goes, what stops everything dissolving into chaos? How do you teach children to write? How does a contract mean anything? How does anyone know what anyone means.

These are fair questions. They’re also, on closer inspection, not really what descriptivism is arguing. Nobody is suggesting chaos. The descriptivist point is simply that language is not a building that requires defending — it’s a process that’s been running continuously for thousands of years, largely without anyone’s permission, and attempting to freeze it at any particular moment is both futile and, in the meantime, faintly exhausting for everyone who just wants to write a sentence.

The evidence for this is, at this point, fairly overwhelming. Every generation produces new words, new constructions, new idioms that the previous generation insists are wrong. Almost all of them survive anyway. The people who insist are eventually outnumbered by people who just use the language and get on with things.

Linguists are almost universally descriptivists. Not because they’re anarchists — Susie Dent aside — but because the evidence points that way. Language changes constantly, always has, always will, and every attempt to freeze it in place is a rearguard action that eventually loses.

This doesn’t mean anything goes. Shared conventions are what make language work — without some common ground, you’re just making noises at each other. Structure matters. Clarity matters. Some rules are genuinely useful.

But the useful ones tend to survive on their own merits, because they make writing clearer and easier to follow. The others — the Latin-derived, bishop-invented, eighteenth-century-confidence variety — survive on inertia and the vague authority of being old.

The only question that actually matters

Here is the reframe that cuts through most of this:

The question is never “Is this allowed?“

The question is “Does this work?“

Those are different questions. The first is about compliance. The second is about communication. And in marketing, communication is the only thing that matters — whether the reader understood you, felt something, and did something as a result.

With that in mind, the things that are actually worth worrying about:

• Clarity: can a normal person read this once and understand it? If not, fix it.
• Rhythm: does it read like a human being wrote it, or like sentences were assembled from available parts? Read it aloud. Your ear will tell you.
• Friction: does the writing move the reader forward, or does it make them work? Every awkward phrase is a small tax on the reader’s attention. Enough of them and they leave.
• Naturalness: would a real person say this? Or has someone rewritten it to avoid ending a sentence with a preposition, producing something no human would voluntarily construct?

Notice that “did I follow the rules?” doesn’t appear on this list.

That’s not because rules are useless. It’s because if you’re asking the right questions, the rules that matter take care of themselves. And the ones that don’t matter… simply don’t matter.

A practical suggestion for the next time this happens

When someone cites a school rule in a content meeting, the useful response is not to argue about whether the rule exists. It usually does exist — as a rule, somewhere, written down by someone who was Very Sure About Things.

The useful response is to shift the question entirely:

“Does it make this clearer or harder to read?“

That’s it. That’s the whole reframe.

Because if the answer is “harder to read” — if avoiding the split infinitive produces a sentence that sounds like it was translated from something — then the rule is actively harming the communication. And no rule that harms communication is worth following in marketing.

And if the answer is “neither, really” — if it genuinely doesn’t affect clarity or naturalness — then it’s a matter of preference, and preferences are not the same as rules, and the meeting can move on. It won’t. But it can.

The single most useful thing you can do as a writer — especially in marketing, where you’re competing for attention with everyone else who ever wrote anything — is to get comfortable with not knowing the rules, and instead knowing what you’re for.

A writer who knows all the rules but not the purpose is just a very conscientious person producing sentences. They’ll never write anything wrong. They’ll also rarely write anything that makes someone stop, read it twice, and feel like whoever wrote this was actually talking to them.

So the next time someone invokes school law in a content meeting, it’s worth asking gently: does this serve the reader, or does it serve the ghost of a teacher from thirty years ago?

The rules were never the point.

The reader was always the point.

Everything else is just scaffolding that forgot to come down.

1
Big Jeff Chaucer, The Canterbury Tales, c.1390: “And whoso fyndeth hym out of swich blame, / They wol come up…“

2
It used to be “thou” for the singular and “you” for the plural, but at some point “thou” went adrift much in the same way we lost the letter Thorn (which looked like þ and sounded like “th”). Thorns died at the hands of history’s greatest monsters: Flemish typesetters. They generally didn’t have the character for their printing presses and started to sub in the letter Y in its place, and the thorn was gradually erased from existence. So all those “Ye Olde Shoppe” signs you see are simply attempts to render “The Olde Shoppe”. In that environment you can see how “Thou” and “You” would gradually get brundlefly-ed together over time, but not before which one you used as the singular version became a big ol’ class issue. Because of course it did. English!

3
Robert Lowth, A Short Introduction to English Grammar, 1762. Lowth was a bishop. He was very confident. He was also, on several points, demonstrably wrong, which didn’t stop his opinions becoming received wisdom for the next two and a half centuries.

4
Boldly split, defiantly human, and nobody has ever once complained. Not even Vulcans, and they bloody love rules.

5
The linguist David Crystal has pointed out that the prohibition on split infinitives is “a nineteenth-century invention” with no basis in historical English usage. Regardless, Latin-fanciers keep trotting it out ad nauseum.

6
It’s also happy to start a sentence with “And”. E.g.: “And I will send a fire on Magog.” The King James Bible is not, by any reasonable measure, a document associated with sloppy thinking. And I’d wager the authors were not overly concerned with your old English teacher’s feelings.

7
Thirty being a conservative estimate on a good day, in a school with functioning heating.

8
This is, incidentally, also a reasonable description of most brand guidelines. But that’s a different blog.

9
Or, more accurately: someone who has confused the map for the territory, which is one of the oldest and most human mistakes there is, so we shouldn’t be too hard on them. But we can be a little bit hard on them.

10
The Commission Générale de Terminologie et de Néologie — a government body whose entire job is to invent French alternatives to English words — also tried their hand at this and proposed “écranique” as a substitute for “selfie“. The French continued to say “selfie“. This has not discouraged the Commission.

11
A lesser writer here would have taken the opportunity to call the Académie a bunch of Cnuts. Thankfully, I am too mature for that.