As you might imagine, most good writers are sticklers when it comes to using proper grammar and punctuation. They cringe when they see apostrophes used to pluralize nouns, the pronoun “your” confused with the contraction “you’re,” or any number of other common mistakes that can creep their way into writing. While it’s always a good idea to eliminate errors from your writing, it’s also important to remember that sometimes it’s ok to break certain rules, especially if it helps you to establish the right tone of voice.

That’s all well and good, provided you know which rules you can break and which ones you can’t. The good news is that the list of rules you can break is a lot shorter than the ones that you can’t. So, as a general rule of thumb, always write the way you were taught to, and then go back and look for opportunities to make your writing more conversational.

To help you get started, below are five of the most common rules that we encourage you to consider breaking from time to time, along with an explanation of why.

Never end a sentence with a preposition

In school we’re taught that ending a sentence with a preposition is nothing short of a cardinal sin. But the reality is that strictly following this rule can often result in language that sounds too formal. Consider the difference between these two sentences:

What software is the new product compatible with?

With which software is the new product compatible?

As readers, we understand both sentences equally well. But doesn’t the first sentence sound more natural than the second? Of course it does and that’s why you should write it that way, even if it means that you’ve got a preposition at the end of your sentence.

Never split an infinitive

Similar to ending sentences with prepositions, we also learn that we’re never supposed to split up the infinitive forms of verbs (e.g., to be, to do, to have, etc.) in writing. That’s often true, but there are times when splitting the infinitive just works better. Think of Star Trek’s famous motto, for example:

To boldly go where no man has gone before.

In that example, the infinitive “to go” is split by the adverb “boldly.” If we were to follow the rules and avoid splitting the infinitive, the sentence would change to the awkward-sounding to go boldly where no man has gone before.

Doesn’t have the same effect, now does it?

Your subjects always have to agree with your verbs

Although this is definitely true 95 percent of the time, there are exceptions. For example, compare the two lines below.

Apple is a great company. It has amazing products that consumers love.

Apple is a great company. They have amazing products that consumers love.

While the first set of sentences is technically the correct one, the second set creates a more personal impression of Apple. Plus, usage like this is so widespread that most people won’t fault you for using this more conversational style.

Never start your sentences with the conjunctions “but,” “and,” “or”

True enough, you don’t want to start most of your sentences with these conjunctions. But doing so selectively (like we just did at the start of this sentence) can help create a better style. The trick is just to use them in moderation, when doing so can help you be more direct or establish a more conversational tone.

Paragraphs need multiple sentences, sentences need multiple words

While these are often hard-fast rules, there are times when they can be broken. Really! Doing so can give the cadence of your writing a much needed adjustment, helping you to keep readers engaged. Just look back at this blog post to see some examples of how we’ve used a combination of sentence and paragraph lengths in our attempt to keep you interested. How’d we do?

Of course, we’ve only scratched the surface here in terms of the rules that you can bend or even occasionally break. What other ones come to mind that you enjoy overlooking in your writing?