As I mentioned then, there is some data that indicates that poor grammar and spelling in writing used to communicate with customers can actually cause them to spend their money elsewhere. So, while your Algebra teacher may have been wrong and you’ve never had to use the quadratic equation in your daily life, what your English teacher taught you DOES matter.
Impact of Grammar on Business Marketing

This week, as I warned, I’m going to get into stuff that’s a little more fine-grained. Specifically, the grammatical issues that pop up in many modes of written communication that businesses have to utilize today: blog posts, as well as posts on Facebook, Twitter, and other social media outlets. So, let’s just get to the point.

Apostrophes are only used for two things: For contractions, and to show possession. They aren’t for decoration.

Apostrophe abuse is rampant. If you don’t believe me, just look at this creatively titled site: And there are dozens more sites, blogs, and Facebook groups that focus exclusively on apostrophes. Errant apostrophes have been known to make people go into intellectual convulsions at the mere sight of a randomly apostrophied word. Right off the bat: Don’t use apostrophes in plural words. Your signage absolutely shouldn’t read, “Banana’s for sale,” “Come try our assortment of pie’s,” or “All writing guide’s 80% off.”

In the English language, apostrophes aren’t available for purchase over the counter. They’re prescription use only, and are used for two very specific functions. The first is for contractions; when we shorten a word or phrase by removing some letters or spaces, we use apostrophes to signal where the shortening–or contraction–has occured. This applies to really common contractions, such as we’re, aren’t, and isn’t. In we’re, the apostrophe stands in for the redacted space and letter “a” in “we_are.” The same goes for aren’t and isn’t (are_not and is_not — yeah, these are a bit messy, perhaps they really should be are’n’t and is’n’t. But… English is dumb). If you’re being a little informal and wanting to represent how many people talk, you can also use apostrophes for slang or verbal accents, such as doin’ for doing or what’d for what did or what would. (As a random aside, ain’t probably originated as an even more abbreviated form of aren’t. Given that some accents drop r sounds, this would result in aren’t being reduced to a’en’t.Ae” isn’t common in written English, especially American English. So the written approximation of that accented slang ended up being ain’t. And then somewhere along the way, people started using it in place of am not and is not as well, because hey, why not.)

The other way apostrophes can be used is to show that something belongs to somebody in some way. John’s blog post, Margaret’s overpriced gym membership, the company’s plan for world domination, the girls’ massive cell phone bills. This can get a little weird to keep straight in some phrases like “three days’ worth of work” or “a day’s pay.” Note the change in apostrophe placement in some of those examples. If you’re talking about stuff that belongs to multiple individuals, then the apostrophe goes after the S (the kids’ pet lobster). Otherwise, it goes before the S — also, the number of things the person owns doesn’t change the placement (the kid’s lobsters).

Now, aside from the most common mistake that people run into with apostrophes–liberally sprinkling them all over plural words like A1 on an overcooked steak–confusion about the above can lead to certain specific errors that seem to crop up a lot.

It’s versus its

To reiterate, English is dumb. This is a good example of that. This pair of words is kind of an exception to the rule. Kind of, but not really. The ONLY time that an apostrophe is to be used in its/it’s is when you’re writing the contraction of the phrase “it_is,” with the apostrophe standing in for the dropped bits.

Whereas, when you’re talking about something belong to “it,” such as “Apple sells its overpriced products for piles of money,” you don’t use an apostrophe. This is because in this case, its is serving as a possessive pronoun (if you remember English class, a pronoun is a word–like I, my, she, our–that stands in for the names of people or things). We don’t use apostrophes in possessive pronouns that end with an S, because in these special cases (its, hers, theirs), the word is already inherently possessive. We don’t need an apostrophe to clue you in that we’re talking about something owning something else.

Let’s versus lets

Thankfully, these words aren’t exceptions to the rule. When you say, “Let’s throw a disco party,” or “Let’s run away to a country with no extradition treaties,” you’re using let’s as a contraction for “let us.” You’re dropping a space and a letter, so we have to stick an apostrophe in there.

When you say, “She lets them go to…” or “This lets you…” you’re talking about someone or something allowing something to occur. You could just as easily change those two examples to “She allows them to go…” or “This allows you…” and it still works. So in this case, we aren’t dropping letters (“She let us them go to…” makes no sense, so that’s also a clue that let’s doesn’t fit there), so we don’t use an apostrophe.

You’re versus your

A lot of people get these two confused. You’re is a contraction for “you are,” so we use an apostrophe for the dropped space and the letter “a.” The word your is a possessive pronoun, just like the version of its that doesn’t have an apostrophe. If you are using you’re/your, and you are confused as to which version is the right one, replace the word with the words “you are.” If your sentence suddenly makes no sense (“You are ex-wife said hi.”), then you know that you want the possessive your. If altered sentence sounds just fine (“You are a boring writer.”), then you want the contraction you’re.

As a side note, if you say “this tax bill is yours,” you still don’t use an apostrophe. It’s a possessive pronoun, so we don’t need an apostrophe to signal possession.

We’re versus were

If you are trying to say that we are doing something, then you use we’re, because it’s a contraction. You dropped a letter and a space. If you are using the past tense version of are, as in “there were dinosaurs back in the days before computers,” then we aren’t dropping any letters or spaces, so we don’t use an apostrophe.

They’re versus their versus there

Okay, now here’s the one that makes everybody nuts. For those who get confused by them, this is where you break out into a cold sweat. For those who do, this mistake is the one that makes you want to break things. It’s a biggie. Of all the specific mistakes described thus far, this one and the your/you’re issue are probably the ones that turn people off the most. Do not mix these up. For the sake of clarity, let’s carefully define each of these.

  • They’re: This is a contraction for “they are.” The apostrophe is the signal that you’re dropping the space and the “a.” You might potentially see it used for “they were” as well, but only in certain spoken dialects or accents. Just worry about “they are.”
  • Their: Like a couple of the other words we’ve discussed, like its and yours, their is a possessive pronoun. We use it when we’re talking about something that belongs to a group of people, such as, “their bag of flaming poo.” It’s also used a lot when people are trying to say something is his or hers, but wants to be all-inclusive. This upsets a lot of grammarians (a heated argument about grammar is a site to behold), but it’s becoming increasingly common, and is considered by many to be acceptable usage.
  • There: This is probably the messiest one. We use there to indicate physical locations (“it’s over there!”). But it can also be used to mark a place in a conversation, or a discussion (“I know my speech is boring, so let’s pause there for a moment,” or “I disagree with you there.”). Perhaps the easiest way to keep this one straight is: if you aren’t trying to say “they are,” and you aren’t talking about something that belongs to someone, then you’re looking for the word there.

Okay. That’s enough talk about apostrophes for today. Moving on.

When can you use an “a,” and when can you use an “an?”

The words “a” and “an” are what are called indefinite articles. They’re words that we use to refer to things, like “a ball,” “a wallet,” “a brick upside the face,” etc. The counterpoint to indefinite articles are definite articles. In English, the only definite article is the word “the.” The difference between the two types is that when we use indefinite articles, we’re not singling out any particular example–we’re being indefinite. With definite articles, we’re singling out very specific things–when your kid asks for “the toy,” if you hand her one at random she’ll scream at you and yell, “I don’t want a toy, I want that one,” because the definite article “the” implied that she was talking about one specific item, not just a toy. Okay, so now that we’ve described what a, an, and the are for, we can now forget all of this.

The question at hand is, when do we say “a thing,” and when do we say “an thing?” The answer is, it’s all about sounds. Specifically, the sound of the first syllable in the word immediately following the “a” or “an.”

When to use “an”

If you’re talking about something whose name begins with a vowel sound (vowels are a, e, i, o, and u, we don’t give a crap about how y is sometimes a vowel in this case), then you use the word “an” before it. The reason we do this is because without the sound of the n in “an,” the “a” would blend into the beginning of the word following it. Cases in point: a apple, a eagle, a igloo, a origami swan, a umbrella. Try and say those examples. It should feel weird. That’s because most people instinctively know when to use an when they’re speaking, because it will feel physically uncomfortable to say “a” right before a word beginning with a vowel sound.

When to use “a”

If we’re dealing with something whose name begins with a consonant sound (any letter that isn’t a vowel), then we use the word “a” to refer to it. Your kid got “a bug” up his nose. Your dog threw up “a box of crayons” all over your couch. Remember how earlier I said we don’t give a crap about the letter y sometimes being a vowel? That’s because we still use “a” for words beginning with y sounds. The boss who fired you rewarded himself with “a yacht.” When the Beatles were in their stoner phase, they all lived on “a yellow submarine.”

Where “a” and “an” get messy

If you look carefully at the rules for “a” and “an,” you’ll notice that I didn’t distinguish between words that begin with consonants or vowels. I distinguished between words that begin with consonant or vowel sounds. Because English is stupid, this creates some exceptions.

  • A lot of words that begin with “ho” have a silent “h.” Some examples include “honor,” “hour,” and “honor/able,” which all begin with “o” sounds. As a consequence, we use “an” with these words. It sounds right, but it looks weird in print. But that’s the way it goes.
  • Those stupid “y” sounds ruin everything. Some words that start with “y” need an “a,” and some words that start with “y” need an “an.”
    • If a “y” word starts with a “you” sound (youthful, Yugo, YouTube), then we use “a.” The reason is because “you” sounds are “y” sounds, not vowel sounds.
      • But what about words that start with a “u” that gives a “you” sound? Unique, union, Uranus. Yep, same deal. It’s about the sound, not the letter. “You” isn’t considered a vowel sound, so we say “a unique Uranusian union.”
  • Acronyms mess everybody up, because everybody gets distracted by the sounds instead of the letters. It all comes down to how the acronym is pronounced. Acronyms that are spoken like words–NATO, SCUBA, SNAFU–can be treated like regular words. The rules still apply. In these three examples, they all start with consonant sounds (“ens” and “esses”), so you use “a” for all of them. In acronyms which are usually pronounced in a spelled-out fashion–USA, FBI, ATM–you have to stop and think about the sound, then apply the rules as necessary.
    • “USA” starts with that dang “you” sound, so you’re going to say “a USA-based business.”
    • “FBI” is pronounced “eff-bee-eye,” so that consonant “eff” sound means “an FBI agent is constantly stalking you.”
    • “SNAFU” starts with an “ess” sound, so the next time you royally screw up at work, your boss will fire you for making “a SNAFU.”

 You should of used could’ve

This is another one that is the written equivalent of two blocks of Styrofoam squealing against each other. If the mere thought of that sound made you cringe, then good. I have your attention. The phrases would have, could have, and should have often get slurred together when speaking informally. When people drop almost the entire word have, including the vee sound, this is usually rendered in writing as woulda, coulda, shoulda. However, in writing, these informal contractions strike many people as being just too sloppy looking in print. Additionally, many people preserve the v in have when speaking.

That easy-to-miss v has led to a lot of confusion, leading to the lexical abominations would of, could of, and should of. No. No no no. No. For the love of all that is holy, no. This is roughly the equivalent of writing they’re as they er, or shouldn’t as should ent–basically, a two word phrase is being abbreviated into a single word, and then being un-abbreviated into two words, with the second one being nonsensical. Since we’re dropping letters, we go back to the rule for abbreviations, which says we replace the dropped letters with an apostrophe. So would have, should have, and would have become would’ve, should’ve, and could’ve.

Many of the mistakes above can be kept to a minimum by keeping your vocabulary simple.

If you have trouble keeping track of all the proper abbreviations, simply don’t use them. There is absolutely nothing wrong with using the un-abbreviated versions of phrases. I know that at times it can feel a little awkward, especially if you tend to speak in your head as you write (I do). However, it’s preferable to be a little more grammatically correct than absolutely necessary, than to make an obvious grammatical mistake that may give a customer a less than ideal impression of your business.

Sometimes I run into situations where I just can’t figure out how to write a sentence correctly. I’ll stubbornly beat my head against a wall for what feels like an hour before I realize that I can just write around the uncertain phrasing. This is a good way to deal with confusion about word choice or grammar. If it doesn’t feel right, delete the whole sentence and find another way of communicating the thought. If you’re saying that such and such “peaked” or “peeked someone’s interest,” and you know something looks wrong (the word in this case is actually piqued), instead of agonizing over it, trash it, say it “caught someone’s interest,” and move on to more important things. Sometimes it takes more time to do something wrong than do it right.

For the five people who made it this far, I think I’ve tortured you enough for one day. Today’s takeaway is that being a little mindful of your writing can result in making a much better impression on your audience. Taking the time to choose your words is worth it.

P.S. There is a difference between “loose” and “lose.”

P.P.S. If you are really committed to upping your writing game, perhaps THE standard for writing guides is Strunk and White’s The Elements of Style. It’s a skinny book, only about a hundred pages, and there are a zillion different editions that have been released. The most well-known and updated version is probably the Fourth Edition. It can be found in just about any used bookstore in the country for about three bucks, and new in Barnes & Noble for about twice that. The original 1918 version is also in the public domain, and can be found online at WikiSource and Project Gutenberg.

The best part about bothering to learn the rules of writing is, once you know them, breaking them isn’t a mistake, you’re just writing with style.

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