Have you ever had the feeling that the people who devised the rules of English grammar did so for the diabolical purpose of making you look bad?

Well, you’re not far from the truth. Even the knowledgeable E. B. White, co-author of the classic writing handbook, The Elements of Style, recognized the complexity and capriciousness of the rules that govern our language when he wrote, “English usage is sometimes more than mere taste, judgment, and education – sometimes it’s sheer luck, like getting across the street.”

To make matters worse, no sooner do we learn a few rules and begin to think we know how to apply them then someone tells us they have changed. Is that fair? It’s like trying to hit a moving target. Let’s see if I can bring some order to the chaos.

First of all, it’s helpful to keep in mind that not all rules were created equal. As Joseph Williams points out in Style: Ten Lessons in Clarity & Grace, many rules have come to us as a consequence of “largely random accumulation” and “not all rules of usage have equal standing with all writers of English, even all careful writers of English.”

To prevent these edicts from getting the better of us, let’s divide them into three categories: There are RULES that you should always observe because they have won almost universal acceptance. There are Rules that you should sometimes observe, depending on your audience and your intended stylistic effect. And there are rules that simply aren’t worth observing. Here are examples of each.

RULES: These are the RULES known to every educated writer: Don’t use double negatives, verbs must agree with their subjects, avoid double comparatives, etc. Other examples in this category are RULES that should be known to every educated writer but sometimes are not: the difference between “it’s” and “its” (“it’s” is a contraction of “it is”; “its” is the possessive pronoun), or the correct use of the reflexive pronoun (used when the subject of the sentence acts upon itself, as in “I hurt myself”; not when a pronoun is used as a subject or object, as in “Jane and myself [should be ‘I’] will attend the meeting” or “You can give the report to either John or myself [should be ‘me’]”).

Rules: These are Rules that you may choose to follow or to ignore, depending on the occasion and your intent. For example, as a general rule a paragraph should have more than one sentence to allow for adequate development. But you may choose to write a one-sentence paragraph for special emphasis. Likewise, as a matter of practice you should express your thought in complete sentences (groups of words that contain subjects and predicates and are not introduced by subordinating conjunctions). But you may choose to use a sentence fragment for special effect. Like this. Keep in mind, however, that when you choose to ignore these Rules, you always pay a price with certain readers who expect you to follow them inflexibly.

rules: I like this category best. If you think about it, knowing that certain rules are not worth observing frees you from a good deal of nonsense. It empowers you as a writer. As evidenced by the practice of many careful writers, you may freely ignore the following:  Never split an infinitive. Never begin a sentence with “because.” Never begin a sentence with “and” or “but.” And never end a sentence with a preposition.

Perhaps Winston Churchill said it best when someone chided him for breaking the preposition rule: “This is the sort of arrant pedantry up with which I will not put.”

And neither should you.

First, you must learn the rules. You must learn that verbs has to agree with their subjects and that you should never use no double negatives. Not to mention them sentence fragments. Second, you must follow the rules. You must remember that “fewer” refers to number (as in “fewer dollars”) and “less” refers to quantity (as in “less money”), despite your hearing and seeing these words misused continually. Third – and here’s the hard part – you must distinguish between valid rules and nonrules.

Here are five that students and readers of my column have asked me about frequently. I want to set you free from all of them.

Don’t split your infinitives.

For 500 years, English writers spit their infinitives without anyone making a fuss about it, but in 1762 the practice was condemned by Robert Lowth in A Short Introduction to English Grammar. His thinking was that, since the infinitive is one word in Latin and cannot be split, it should not be split in English. How’s that for logic?

In a letter to the Times, Bernard Shaw dealt with the issue this way: “There is a busybody on your staff who devotes a lot of his time to chasing split infinitives. Every good literary craftsman splits his infinitives when the sense demands it. I call for the immediate dismissal of this pedant. It is of no consequence whether he decides to go quickly or quickly to go or to quickly go. The important thing is that he should go at once.”

Never end a sentence with a preposition.

How else would you say, “What are you looking for?” As a matter of emphasis, you should end a sentence with an important word, but sometimes the most natural word order puts the preposition at the end.

Never begin a sentence with “and” or “but.”

Beginning sentences with “and” or “but” is an effective technique for picking up the rhythm of your writing and creating a conversational effect. The American Heritage Dictionary offers this perspective: “It is frequently asserted that sentences beginning with and or but express ‘incomplete thoughts’ and are therefore incorrect. But this rule was ridiculed by grammarians [such as] Wilson Follett (who ascribed it to ‘schoolmarmish rhetoric’) and H. W. Fowler (who called it a ‘superstition’), and the stricture has been ignored by writers from Shakespeare to Virginia Woolf.”

Never begin a sentence with “because.”

Beginning a sentence with “because” is an excellent method for subordinating one part of a sentence and emphasizing another, as in “Because you have worked so hard this year, you will receive a $10,000 bonus.” This myth apparently originated from teachers warning their students not to write sentence fragments beginning with “because,” as in “Because you have worked so hard this year.” According to Joseph Williams, “It is a ‘rule’ with utterly no substance.”

Never write single-sentence paragraphs.

Although a series of single-sentence paragraphs will preclude full development of your thoughts and result in a disjointed, staccato style, an occasional single-sentence paragraph is a perfectly acceptable technique for creating emphasis. Even Strunk and White, the sometimes stodgy coauthors of the classic The Elements of Style, give us permission to use a single “sentence of transition” to indicate “the relation between the parts of an exposition or argument.”

So the next time someone confronts you with a rule of dubious origin, remember what Henry David Thoreau once said: “Any fool can make a rule and every fool will mind it.”