Words That Trick Everyone

Say “there,” “their,” and “they're” out loud, one after another. They sound exactly the same, don't they? That's exactly why they cause more first-draft mistakes than almost any other words in English — your ear can't warn you when you reach for the wrong one, so while you're focused on the story instead of the spelling, it slips through.

A handful of pairs and trios work this way, sounding identical but meaning completely different things:

• to / too / two — to (direction: to the castle), too (also, or excessively: too far), two (the number: two swords).
• their / there / they're — their (belongs to them: their map), there (a place: over there), they're (they are: they're leaving).
• its / it's — its (belongs to it: the dog wagged its tail), it's (it is or it has: it's raining).
• your / you're — your (belongs to you: your turn), you're (you are: you're next).

A trick that actually works

Why do “its” and “you're” trip up even careful writers more than the others? Because the apostrophe there doesn't mean possession the way it usually does — it's standing in for a missing letter, short for “it is” and “you are.” That can feel backwards at first, since almost everywhere else in English, an apostrophe means something belongs to someone.

There's a simple test that clears it up: replace the word with “it is” or “you are,” and see if the sentence still makes sense. “The dog wagged it is tail” doesn't work, so the correct word is “its.” “You are next” does work, so the correct word is “you're.” That one substitution catches most of the mistakes in this entire lesson, every single time.