Writing that's easier and more fun to read...

5 Breakable Grammar Rules Your English Teacher Force-Fed You

My high-school English teacher stuffed my innocent brain inside a box. And, it has taken me countless sweat-drenched hours to break free.

Happened to you, also?

Well, it’s time to escape that frustrating trap.

Gary Bencivenga once said, “Writing is thinking on paper.”

But, it’s difficult to think freely, when your mind is still stuck in homeroom. All because of those stifling grammar rules your English teacher force-fed you!

That’s why today, we’ll discuss five breakable grammar rules.

The result?

Your thoughts will flow. Your words will flow. Your cash will flow.

And, your wealth will grow.

So, let’s break some rules!

Breakable Rule #1:  Never End a Sentence with a Preposition!

Smash that rule. Why?

Because often, when you follow it, you compose stilted writing. It’s like a pianist hitting a wrong note while playing. You just feel it.

And, your reader does, as well.

Your copy must speak to your reader. Why?

Because research shows your reader hears what you write. When you end your sentences with prepositions, you’re being conversational.

As Bob Bly once said…

“Ending a sentence with a preposition adds to the conversational tone of the copy.”

Here’s an example from one of Gary Halbert’s ads:

“In fact, I’m going to tell you some things about this amazing gambling game that you’ve probably never heard before.”

Think the target of Gary’s ad complained that his sentence ends with “before”?

Likely not.

But, your English teacher likely would.

End your sentences with prepositions when necessary. And, if you receive pushback from the grammar police, here’s Merriam Webster’s emphatic message for them:

“If you don’t like to end your sentences with prepositions, you don’t have to — just don’t say that it is a rule.”

Breakable Rule #2:  Avoid Sentence Fragments At All Costs!

Yes, violate that rule, as well.

When used correctly, a sentence fragment can pull your reader deeper into the text. Why? Because, often, a fragment is unexpected. And, one of the keys to keeping readers engaged is being unpredictable… in a good way.

That’s why Gary Halbert once said…

“Use short sentences. Short paragraphs. Everyday English. Use some one-word sentences. Use some one-sentence paragraphs.”

The result?

Your copy will have a pulse.

So, dabble in the occasional sentence fragment — as long as you’re not fragmenting your message.

Also, you can use a sentence fragment to hammer your point. Swiftly.

Here’s an example from a John Carlton ad:

“Is Darrell some kind of superman? Nope.”

John opened the door, then slammed it shut.

Breakable Rule #3:  Never Begin a Sentence with a Conjunction!

Yup, scrap that rule, too.

After doing so, you’ll have a tool you can use to slice prolonged sentences. Specifically, the ones crowded with multiple thoughts.

So, place a conjunction in front of some of your sentences. Give your thoughts breathing room.

In fact, try focusing on one thought per sentence. When you do, your message will become easier to grasp.

As Bob Bly once said…

“Beginning a sentence with and, or, but, or for makes for a smooth, easy transition between thoughts.”

Here’s an example from John Caples:

“And then I explained how for years I had longed to play the piano.”

Breakable Rule #4:  Don’t Split Infinitives!

Another rule you should break.

By the way, if you don’t know what an infinitive is, you’re not alone. I don’t recall my English teacher writing that term on the blackboard. But, I’m certain I’ve had the “don’t split infinitives” rule drilled into my head from somewhere. Because, every time I do it, a pesky voice tells me I’m committing a literary crime.

That said, look at the phrase “to ignore.” That’s an example of an infinitive. But, if you insert “quickly” between “to” and “ignore,” you’re splitting an infinitive. So, “to quickly ignore” is a split infinitive.

And, guess what? According to MLA Style Center, it’s now okay to split infinitives. Why?

Because, they realize “words should always be arranged in a way that makes the meaning of a sentence clear.”

Breakable Rule #5:  Dodge Contractions!

Okay, I want you to not only break that rule, but crush it.

Because, when we communicate, there’s no inner critic who filters contractions from our speech. Contractions flow from us freely when we speak.

As Clayton Makepeace put it:

“I make liberal use of contractions. After all — it’s how people talk! In fact, the only time I write ‘does not’ instead of ‘doesn’t’ is when the ‘not’ is crucial to my meaning. And, if it’s really crucial, I’ll add emphasis to it with an underline, italicizing it, capitalizing it, and in some cases, all of the above.”

Fact is, we’re talking to our readers via copy. So, why restrict ourselves?

We’re no longer confined to the rigid walls of classrooms. We now inhabit the limitless terrain of the internet.

So, when you write, use contractions.

Here’s an example from Eugene Schwartz:

“You’re going to do it in a special way, of course. With a special goal. And with a whole, beautifully-thought-out technique.”

Notice how his first sentence began with a contraction. Then, he used two sentence fragments, consecutively. And, he led with a conjunction for his third sentence.

But, you know what? It all flowed. And, his point was clear.

Isn’t that what matters most?

Escape the Classroom, Free Your Mind

As a web writer, you no longer have to worry about cold, stern looks from your English teacher. You no longer have to fear the threat of a giant, red “F” at the top of your paper.

So, don’t get so hung up on grammar rules that unintentionally block the flow of your thoughts. Instead of focusing on grammar, focus on clarity. Because, at its core, the purpose of grammar is clarity.

That means, if a grammar rule defies clarity, it’s your right — better yet… it’s your duty — to break that rule, in service of your reader.

In the end, your copy is graded by your reader’s response. And, if they respond well, that’s your giant, red “A” with a gold star next to it for good measure!

Darek Black

Darek Black

Darek Black is a copywriter and the co-founder of Content Stride (https://contentstride.com), a copywriting and graphic design company. His articles have appeared in B2B Writing Success, JeffBullas.com, Addicted 2 Success, and Content Marketing Institute.


  • Darek…

    You’ve set me free!
    And I’m certain I’m going to quickly ignore the grammar rules I learned decades ago.


    P.S. It’ll be challenging. Yup!
    But I’ll work on it.

    ~Cindy Mae

  • I remember the humor in the preposition rule and the little ditty they taught us to use to obey this rule: “A preposition you should never end a sentence with!” Isn’t that just hilarious?

Leave a Comment

Scroll to Top