Someone's gone and written a whole book on semicolons.
Which, now that I'm aware of it, I've put on my "read someday" list. Meanwhile, it's been Nationally Reviewed, that being how it came to my attention, so I'll comment on a few things in Joseph Epstein's review.
I don’t believe I used my first semicolon until the age of 24 or so
One or both of us must be atypical; I believe I started using semicolons in elementary school. (Nowadays, as a C programmer, I give the old ';' key quite the workout.)
Rules turn out to be Cecelia Watson’s bête noire. In the middle of her book she questions the authority of The Chicago Manual of Style, Strunk and White, H. W. Fowler, and others, writing that “it’s fair to ask why we consider these books authoritative, and if there might not be some better way to assess our writing rather than through their dicta.”
Thing is: you really need to learn the rules before you start breaking them; this is yet another fine example of Chesterton's Fence. Develop proficiency in Standard English, and you can then develop a personal style which is simultaneously intelligible, informative, and idiosyncratic. (Yes, folks, it is eminently possible to write technical reports in a style which will clearly convey the necessary information, hold the reader's attention, and ensure that the author is noticed by higher-ups.)
As for rules, some are more valuable than others. Take that most school-marmish among them, that of never ending a sentence with a preposition.
I consider the rule against splitting infinitives worse, as it it's rooted in the idea that English should follow Latin grammar. In Latin, infinitives simply cannot be split; in English, splitting an infinitive is sometimes the most concise way to express the intended concept, and the recommended alternatives often exhibit the dual disadvantages of being clunky and of not actually meaning the same thing.
In writing as in just about everything else, while at it, what the hell, you may as well get it right.
True enough, keeping in mind that the English language allows considerable flexibility with regard to "getting it right", particularly where style is concerned. (Note use of programmer punctuation there, as opposed to stylebook punctuation. I'm still not fully consistent about that.)
... And, yeah, I really should review the stylebooks every few years, so as to keep from drifting too far from the norm. Not this month, though; they're packed, along with most of the other books.
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