By the time we’re waist-deep in our careers, we don’t worry what our high-school teachers would think. Or so we tell ourselves.

There’s one big, common exception. When people sit down to write anything others will read, they spend an awful lot of time remembering their English teachers. Some people have specific flashbacks in mind, but all of us know that stern and critical feeling—and 99% of the time, it just gets in the way. So what can we do about it?

If you’re nodding along right now, you’re truly not alone. In fact, you might be in the majority here.

Back when we worked in book publishing, we noticed that almost every single new author (whether 30 or 70 years old) had the Ghost of Teachers Past hovering over their shoulder during the writing process. Philosophers would call that a “Cartesian demon,” a voice in your head that always tells you you’re wrong even when you’re 100% right.

Let’s try and free you from those bonds, or at least loosen them a bit. We’re professional* copywriters, so we’ll share what our experience has taught us.

The better you know the rules, the more qualified you are to break them. This doesn’t mean that your English teacher was right about everything. In fact, now that you’re no longer a teenager, let’s look back and clear up why grammar teachers can be such neurotic hard-asses: The rules of English have plenty of nuances and exceptions, but good luck teaching them to 30 hormonal teenagers at a time. This is one area where (what is at root) an industrial education system is NOT equipped to share knowledge effectively.

Here’s the other thing about our English teachers: most of them didn’t spend time as professional copywriters (per se), in a role where they were continuously writing content for a non-captive audience. Since we do fit that description, we’ll tell you what becomes inescapably clear over time: Nothing matters unless it matters to the reader. If your readers care about something, it matters. Otherwise, the rules are more like guidelines and welcome aboard the Black Pearl.

If you’re a regular reader of theCLIKK, you’ve probably noticed two things: (1) our copy generally has its s**t together, but (2) it’s also pretty shameless about bending certain conventions, especially for the sake of conversational tone. In other words: we follow the rules pretty closely until we don’t, and both of those parts work because we…

Break rules for effect, not efficiency. In other words: we assume that the rules exist for a reason, and that we always need a better reason in order to break a rule safely. That ‘better reason’ is always some version of improving the effect for the reader (because remember, nothing matters unless it matters to the reader).

The opposite of breaking a rule for effect is breaking it for efficiency—meaning either (A) you’re being somehow lazy, which is a nut we won’t try to crack, or (B) you’re not yet able to express the idea in clean-and-correct writing. In either case (but especially the latter), you should definitely write down “the Raw Version” because it could be useful to you in one of two ways:

🎯 Helping paint the target you’ll need to hit with the final draft. The central challenge of writing is getting other people to see the same picture in their heads that you see in yours—but you can’t even begin that central challenge until you have your own clear view of what you’ll be showing your readers. Your rough draft only needs to makes sense to you; it doesn’t matter if it’s gibberish to everyone else because, well, they won’t be reading it yet!

🧩 In some cases, the Raw Version will fit best. Sometimes the very first sentence you spit out works better than any of the edits after it.

Don’t take dumb chances. That’s our umbrella rule for a few smaller rules:

🚫 If you’re not sure there’s a benefit to breaking the rule, just don’t. We get it… phrasing can be difficult. It’s tempting to leave the quick and dirty version on the page. But if you know you can do better and choose not to, that’s laziness (spoken from our own experience checking ourselves).

📖 Double-check the dictionary, even if you feel silly. True story: one time, we mixed up the words ‘aphrodisiac’ and ‘amnesiac’ and said Jason Bourne was the former when we meant the latter. Hilarity ensued.

In case you didn’t know, there’s a Google shortcut for looking up dictionary definitions. Just go to Google and type ‘define’ and then the word in question (like ‘define aphrodisiac‘).

😎 Don’t include jokes unless it doesn’t matter if people laugh. We have fun writing this newsletter, and y’all tell us that you have fun reading it, but we’re not comedians (and even if we were, we couldn’t possibly hear you laughing). We don’t try to write jokes; we try to write good copy with a twist of smart-ass, and the jokes often present themselves as we go.

We like this rule because it’s a no-lose strategy. Either y’all laugh and that’s a nice bonus, or you don’t and the copy still serves a purpose.

Last but not least:

When in doubt, ask an editor. We’ll use our last couple sentences here to dispel a common misconception: editors are NOT bitter killjoys by nature. You might think “an editor is a paid, professional Grammar Nazi,” and you might therefore believe that hiring an editor will be like a root canal for your rough draft—or perhaps worse, like turning in a paper to your old English teacher.

Fear not. Editors are people too, and they know that this stuff can be daunting. Like any sort of professional, they’re here to help; just do your best to communicate what you need.

* In his wonderful book On Writing, Stephen King defined a good standard for whether or not you’re a professional writer. Basically: if you get paid for something you write, the paycheck doesn’t bounce, and you can pay the light bill with the money, you’re a professional writer. By that standard, we have collective decades of professional writing experience.

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