There’s [Grammar] Hell to Pay If You Break These Rules

by | Oct 12, 2009 | Writing Matters Blog | 2 comments

Grammar rules die hard. I learned that after my post Five Grammar Rules That Beg To Be Broken. I heard from a number of readers who, invoking the ghosts of eighth grade English teachers past, refused to break the rules. Despite my advice, they will not split infinitives or end a sentence with a preposition—ever.

The English language is changing. But some of the rules that we learned are still hard and fast.  Here’s my top five grammar and usage rules that should not be broken. Breaking these rules will land you in grammar hell, where you’ll have to diagram sentences and speak to your eighth grade English teacher in complete sentences—for eternity. 

1. Possession Is 9/10th of The Apostrophe Rule
The apostrophe doesn’t do heavy lifting. Its two main jobs are standing in for missing letters in a contraction and showing possession or ownership. Despite its slim task roster, it’s subject to more than its fair share of abuse. In its job of indicating possession, an apostrophe between the noun and the s shows singular possession. For example, “the doctor’s office” indicates that the office belongs to one doctor. Placing the apostrophe after the s with a plural noun, “the doctors’ office,” shows that the office belongs to more than one doctor.

Some misguided people feel compelled to put the apostrophe between any noun and an s. “The doctor’s have a large office.” This is incorrect. Remember, the apostrophe indicates that the noun is possessive, not plural.

2. Its or It’s? Small Words Big Difference
Confusing it’s and its is probably the grammar error I see most frequently.

  • It’s is a contraction for it is. “It’s the best pizza I’ve ever eaten.” 
  • Its is a possessive pronoun. “Remove the pizza from its box before reheating.” As one of the oddities of the English language, despite indicating possession (See #1), its does not have an apostrophe.

3. “It’s Me, Not I”

For some reason, me has gotten a bad rap. People think that using I is classier or more correct. The truth is me is high class enough when used correctly. So when is that? Me is correct when it is the object of the sentence or object of the preposition—not the subject. “John went to the ballgame with me” is correct because in this sentence John is the subject and me is the object of the preposition. 

The confusion between I and me crops up when there is a compound object. “John went to the ballgame with Susan and me.” You don’t need to grapple with parts of speech to figure this out. Let your ear be the judge. Take away Susan and you are left with “John went to the ballgame with me.” “John went to the ballgame with I” sounds—and is—incorrect.

4. Subject-Verb Disagreement
Errors in subject-verb agreement are also common. The rule is simple enough. A singular subject requires a singular verb. A plural subject requires a plural verb. The problem occurs when writers incorrectly identify the subject.

  • Incorrect: “A good set of tools make repairs easier.” This is incorrect because set (singular) not tools (plural) is the subject.
  • Correct: “A good set of tools makes repairs easier.”

(For those who have difficult identifying the subject of the sentence, try diagramming!)

5. Punctuation with Quotes: Insider’s Rules

A common conundrum: when you have quotation marks combined with other punctuation—comma, period, question mark—do these other punctuation marks go inside or outside the quotation marks? 

In American usage (Chicago Manual of Style Online), periods and commas always go inside the quotation marks. Other punctuation marks—colons, semicolons, question marks, and exclamation points—all go outside the quotation marks unless a question mark or an exclamation point is part of the quoted matter.

  • The boss asked all employees, “Will you take a cut in pay?” In this example, the question mark goes before the quotation marks because it is part of the quoted matter.
  • Did you hear that the boss asked all employees, “Will you take a cut in pay”? In this example, the question mark goes outside of the quotation marks because it applies to the whole sentence, not just the quotation.

Does breaking any of these rules spell surefire disaster for your business or career? That depends. Lands’ End has made a small fortune despite a misplaced apostrophe.  President George W. Bush was not impeached for his subject-verb disagreement: “Is our children learning?”  And Barack Obama—President, Harvard Law Review editor, and book author—has incorrectly used I instead of me repeatedly:  “a very personal decision for Michelle and I.”

So, you may escape cataclysmic ruin in this life and even prosper if you break these rules. But then there’s the afterlife in grammar hell!

Tags: Editing, Grammar and usage, Punctuation, Usage, Writing


  1. Blogs are good for every one where we get lots of information for any topics nice job keep it up !

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