HOMONYMS….Back when I was VP

HOMONYMS….Back when I was VP of Marketing at Kofax Image Products, I spent a lot of time reviewing and editing other people’s writing. One thing I noticed was that the most common spelling errors were for words that sounded alike, such as “there” and “their,” and I had the bright idea that if that was really the problem, it shouldn’t be too hard to turn people into better spellers. After all, the universe of homonyms is much smaller than the total universe of words.

Very shortly, of course, I realized that I was an idiot. It’s not that homonyms are really the words people have the hardest time with, it’s just that all their other misspellings are caught and corrected by automatic spell checkers.

Still, the basic idea is sound: given that most of our misspellings are now corrected for us by computers, the only thing standing between us and perfect spelling is homonyms. My experience is that about two-thirds of misspellings can be traced to a dozen or so pairs of homonyms, which means that there’s good news for bad spellers: if you can just manage to memorize this list (and keep your spell checker on), your documents will look pretty much perfect ? spelling wise, anyway. So here it is:

Homonyms	Usage Rule
They’re vs. their vs. there	“They’re” always means “they are.” “Their” involves possession of some kind (“their books,” meaning “books that belong to them.”) Use “there” in all other cases.
You’re vs. your	“You’re” always means “you are.” Use “your” in all other cases.
It’s vs. its	“It’s” always means “it is” (or “it was”). Use “its” in all other cases.
Too vs to (nobody seems to have trouble with “two”)	“Too” means either “also” or “excessively.” Use “to” in all other cases.
Who’s vs. whose	“Who’s” always means “who is.” Use “whose” in all other cases.
Lose vs. loose	“Lose” is the word that’s pronounced “looz” while “loose” is pronounced “looss.” This is actually the best quickie definition since both words can be used in a wide variety of ways.
Write vs. right	“Write” means putting words on a page. Use “right” in all other cases.
Deer vs. dear	“Deer” is an animal. Use “dear” in all other cases.
We’ll vs. will	“We’ll” always means “we will.” Use “will” in all other cases.
Hear vs. here (and “hear, hear” vs. “here, here”)	“Hear” is what you do with your ears. Use “here” in all other cases. (And “hear, hear” is the correct phrase meaning “damn right.”)
Plain vs. plane	“Plain” means either “not fancy” or a “flat expanse of land,” like the Great Plains. Use “plane” in all other cases.
New vs. knew	“New” means “not old.” Use “knew” in all other cases.

This list is more or less in the order that I seemed to encounter them, from most commonly misspelled to least. And if even this list seems like too much work to memorize, there’s more good news: the top six are really the killers. They seemed to account for about half of all the misspellings I encountered.

The nice thing is that in most of these cases one of the words has a pretty firm meaning, and all you have to do is check to see if that meaning fits what you want to say. If it doesn’t, just use the other spelling ? there’s no need to bother memorizing its variant uses.

UPDATE: By popular demand, here’s a couple more:

Homonyms	Usage Rule
Effect vs. affect	“Effect” is usually a noun, so it has “an” or “the” before it. In all other cases, use “affect.” This is not a foolproof guide, but it’s close….
Site vs. sight	“Site” means a place where something is located: “the site of the Taj Mahal,” or a “website.” Use “sight” in all other cases. (And don’t even bother with “cite”; just use another word unless you’re sure you have it right.)

UPDATE 2: Kieran Healy goes beyond spelling and offers some additional practical advice on writing.