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Unlike a lot of copywriters out there, I think that  good writing is crucial to good copywriting.

A lot has been written about how ad copy isn’t the same as fiction. I agree. But I think the point can be over-stated; for instance, when people say “you don’t need to be a good writer to be a good copywriter.”

That’s taking the whole thing a little bit too far.

Grammar, word choice, punctuation, and style all play a role in crafting great copy. The technical stuff matters, because people don’t want to buy from someone who sounds like an idiot. But they don’t want to buy from someone who sounds like an egghead either; the style you’re going for may range from smutty (Warrior Forum-style internet marketing) to classy (Vanity Fair ads), but never dull, dry or pedantic.

That said, for 99% of marketing, you don’t need to be a grammar nazi. In fact, being too grammar-conscious can hurt you. It can make you sound stiff, dry, dull and boring.

With that in mind, here are the top 5 grammar rules you can–and should–break whenever you feel it necessary.

1. Using ‘Less’ When ‘Fewer’ Is Technically Correct.

Technically, ‘less’ is used to describe a smaller quantity of something that isn’t countable, while ‘fewer’ is used to describe a lower number of something that is countable. You really don’t need to follow this one–the distinction is borderline outdated and most people don’t follow it anyway.

2. Split Infinitives.

A split infinitive is a phrase that where an adverb is inserted between the word ‘to’ and a verb.


“She seems to really like it.

This rule has always struck me as extremely stupid, and even the most educated people routinely break it. Actually following this insipid rule practically guarantees your writing will suffer.

3. Period Inside Quotation Marks.

Periods are supposed to be placed inside quotation marks, “like this.” They are not supposed to go outside the quotation marks, “like this”.

I follow this rule about 90% of the time, but there are situations where it’s OK to break it. For example, if you have a sentences inside a set of parentheses, it makes sense to put the period outside the closing bracket, (“like this”).

The reason I favor doing this is because the closing bracket is the end of the sentence. Imagine if you had a sentence with three sets of parentheses, like this:

(lorem  (lorem ipsem (“lorem ipsem.”)))

This sentence would just feel like it needed a period at the end of that final bracket; changing the position from inside the quotation marks to outside the brackets would improve the flow of the writing.

4. Passive Voice.

One of the most commonly shared pieces of advice about writing is “don’t use passive voice.” This is not exactly in the domain of grammar, but editors tend to frown on passive constructions so much that it may as well be.

If you’re not aware, an active voice construction is one where the agent (person) is the most important part of the sentence; whereas a passive voice construction is one where the object of the sentence is the most important part.


Active: Sam rang the bell.

Passive: The bell was rung by Sam.

Generally, it is better to use active voice instead of passive voice. It’s more direct, assertive, and concise 99% of the time.

But there are situations when it can be better to use passive voice. Let’s take, for instance, the opening words to The Declaration Of Independence: 

We hold these truths to be self-evident, that all men are created equal, that they are endowed by their Creator with certain unalienable Rights…

This is definitely a passive construction; the object (“all men”) comes before the agent (“creator”). And it makes perfect sense, because the declaration of independence is fundamentally a document about people and their rights, not about “the creator.”

If Jefferson had written, “in the beginning, God created all men equal, and endowed them with certain inalienable rights,” the Declaration would have sounded like a religious text, not a legal one.

5. Whom.

Who vs. Whom can be a contentious topic.

Technically, “who” refers to a person in the subjective case (“who is he?”); while “whom” refers to an unspecified person in the objective case (“three men, two of whom were Irish”).

The rule regarding who vs. whom is one that most people don’t pay attention to nowadays. It would be pretty rare to see use of the word ‘whom‘ even on the op-ed pages of the New York Times. Nevertheless, it’s not unheard-of for college professors to insist on the ‘proper’ (archaic) uses of who and whom, so it’s important to point out that in real-world writing the distinction doesn’t matter much anymore.


One saying I don’t like very much is, “rules are made to be broken.” In my own opinion, if a rule is any good, it should probably be followed, at least by people who are not yet experts in a subject. But it’s nonetheless true that many rules are outdated and ripe for breaking. This article is hardly a complete list of such rules, but it’s a good start

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