Bruce Byfield has a brilliant analysis of the origins of, and problems with, prescriptivism called “Tech Writers, Grammar, and the Prescriptive Attitude.” I urge anyone interested in the topic to read it; I’ll just quote a bit that I particularly want to emphasize:
Writing well, as George Orwell observes in “Politics and the English Language,” “has nothing to do with correct grammar and syntax.” If it did, then two centuries of prescriptive grammar in the classroom should have resulted in higher standards of writing. Yet there is no evidence that the language is used more skillfully in 2001 than in 1750. The truth is that, prescriptive grammar and effective use of English have almost no connection. A passage can meet the highest prescriptive standards and still convey little if its thoughts are not clearly expressed or organized. Conversely, a passage can have several grammatical mistakes per line and still be comprehensible and informative. Prescriptive grammars are interesting as a first attempt to approach the subject of language, but today they are as useless to writers as they are to linguists. So long as writers have a basic competence in English, prescriptive grammar is largely a distraction that keeps them from focusing on the needs of their work.
There’s nothing wrong with following the “rules” if you enjoy playing that game (or if it’s required by the publication you’re writing for), but it has nothing to do with the quality of your writing, which is (or should be) paramount. I also recommend Jean Hollis Weber’s fine piece on the proper focus of editing, “Escape From the Grammar Trap.”
Thanks to aldiboronti of Wordorigins.org for the link to Echo Tan’s blog X Reverie, where I first saw these articles posted, and to suchi in the comments below for the proper attribution.