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Troublemakers: Learning the Rules (So You Can Break Them)

“Learn the rules like a pro so you can break them like an artist.”

~Pablo Picasso

There’s a rule I follow when it comes to breaking the rules. While that might sound counterintuitive, it will hopefully all make sense in a minute. While I’m mostly talking about grammar and the like in this article, this rule can be applied in many other areas of business and life as well. Make sense? Good. So here’s my rule:

You can break any rule of the English language you want, so long as you know and understand it first.

What exactly do I mean by that? Let me put it another way. The rules of the English language are put in place for a reason—they help to clarify meaning and avoid confusion when you’re communicating. But grammar rules don’t (and shouldn’t) exist just for the sake of having rules. They’re meant to facilitate communication, and if they’re not doing that, then what’s the point? Sometimes, they even get in the way. It’s okay to break the rules from time to time, so long as you’re not doing so out of ignorance.

Breaking the Rules

Anyone who’s ever suffered through a high school English class has probably had grammar rule after grammar rule drilled into them by a teacher. In my experience, most people come out of those classes in one of two ways:

  1. They cram for 20 minutes before the test to get the minimum passing grade, then forget everything they learned 20 minutes after the test is over.
  2. They study and internalize the rules of the English language for the rest of their lives, correcting any small mistake and physically wincing any time someone uses the word “who” when they should have said “whom.” See also: Grammar Nazi

Of course, neither of these philosophies is really the right way to go about it, but what are you gonna do? These are high schoolers, remember; it’s a fair assumption that they’ll cling to an extreme and assume it’s the only right choice. I’ll fully admit that I used to be deeply entrenched in the second group. After all, I’m a writer. I love language, and rules are rules for a reason. If you break a rule, then you’ve clearly done something wrong… Right?


Sometimes, it’s okay to break the rules. In fact, sometimes it’s even advisable. But before you break any rules, it’s important to know what you’re doing. When is it okay to break the rules of grammar?

For example, is it okay to have a paragraph that’s made up of only one sentence?

How about four words?

Or two?


Of course, when you read books and essays from the greats—authors like Jane Austen, Charles Dickens, William Faulkner, E. E. Cummings, and even (perhaps especially) William Shakespeare—you see that they broke grammar rules all the time:

  • Jane Austen often used double negatives. She used convoluted language when describing pretentious characters to highlight their high opinions of themselves.
  • Charles Dickens was notorious for his run-on sentences. The first sentence of A Tale of Two Cities was 120 words long. (Of course, he was also paid by the word, so make of that what you will.)
  • Almost an opposite case to Dickens, William Faulkner had no qualms about starting a sentence with a conjunction.
  • E. E. Cummings (or “E.E. Cummings,” as he sometimes wrote it) took exceeding liberties with capitalization. While he followed standard capitalization conventions in some of his poems, others used none whatsoever, and more were intentionally inconsistent in which rules they followed.
  • William Shakespeare broke many linguistic conventions (and is the source of just as many). For example, he wouldn’t hesitate to end a sentence with a preposition, a no-no that will set many modern-day linguistic prescriptivists’ mouths to foaming. But as the quote (often misattributed to Winston Churchill) says, that rule often leads to “the sort of English up with which I will not put.”

Learning the Rules

So if it’s okay to break the rules, then what’s the point of learning the rules in the first place? In fact, what’s the point of actually having rules if it’s okay to break them?

Here’s the thing—it’s only okay to break the rules if you know that you’re breaking them. If you break the rules, you are typically doing it for a reason. You’re intentionally going against convention, and that’s going to draw attention—which might be exactly what you want. But your audience is also going to be at least somewhat familiar with those rules, and if there’s no clear purpose behind you breaking a rule? It just looks like you made a mistake. And making a mistake, particularly in the world of internet comments, is going to draw attention from your message and focus it on your error. Don’t get me wrong—forgetting a rule isn’t necessarily a death sentence, but it will definitely hurt your credibility.

You can bet that when these literary greats were breaking rules, they knew exactly what they were doing. When E.E. Cummings refused to capitalize his name or the pronoun “I,” it wasn’t the same as using “they’re” instead of “their.” He did it for a reason and used his breaking of convention to set himself apart.

The “Why?”

So what does all this have to do with marketing?

An enormous part of marketing today involves content creation. But content marketing isn’t just about shoveling as many words as possible out the door. Your content has to be relevant. It has to be engaging. It has to be something that will catch the attention of your intended audience. You don’t just want a reader to click on a link—you want to keep them coming back. This willingness to break rules in artistic, intentional ways doesn’t only apply to writing, either. It extends to photography, infographics, podcasts, videos, and any other type of content you can imagine. Once a good idea hits the internet, it’s typically picked up immediately by dozens, if not hundreds, of imitators. With the notoriously short attention spans of the average consumer these days, it’s important to find a way to set your content apart without sacrificing quality.

So learn the rules. Become so familiar with them that they’re like second nature. That way, when you do decide to break the rules you can break them properly. When a jeweler is cutting a diamond, he doesn’t just pick a random spot to make his first cut. He studies the gem thoroughly and becomes intimately familiar with it before he begins cutting. If he does it wrong, rather than cutting the diamond into a beautiful shape, he could accidentally shatter it into dozens of tiny, near-worthless pieces. If you’re not careful, the same thing could happen to the content you produce.

Sometimes, it’s okay to break a few grammar rules—so long as you know why you’re breaking them. Perhaps it’s too add emphasis to a certain point. Maybe it’s to make a piece flow better. Maybe it’s just to give yourself a more distinct voice. Just be willing to break a rule from time to time—so long as you understand it. Take it from a company that breaks the rules as the very first thing you see on our homepage:

Digital. Marketing. Elevated.

*Feature Image Photo by Edward Simpson from London, England (Break the rules!) [CC BY-SA 2.0 (http://creativecommons.org/licenses/by-sa/2.0)], via Wikimedia Commons

Source: https://upload.wikimedia.org/wikipedia/commons/f/fe/Break_the_rules%21_%282177819899%29.jpg

Bill Giles

Bill is a Writer and Content Manager at 97th Floor.

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