As a writing tutor in Boston I try to keep track of various resources that give advice on writing. One thing I've noticed is that, more often than not, advice on writing takes the form of rules.
Often these are lists of rules. If you google "writing advice" you'll come up with Walter Benjamin's "13 Theses on Writing," Henry Miller's "11 Commandments of Writing," David Ogilvy's "10 No-bullshit Tips on Writing," Kurt Vonnegut's "8 Rules For a Great Story," Zadie Smith's "10 Rules of Writing," Stephen Greenblatt's "10 Rules and a Desire," and on and on and on. Making a list of writing rules seems like practically its own genre now, alongside the short story, the novel, and the essay.
You can read these lists if you want. They can be inspiring, funny, insightful--just like the authors who wrote them. But if you start looking through the lists, you'll begin to notice something. All the lists are different. Not even the numbers are the same. Why might this be?
I suppose you could write an entire book on the different lists of rules and how they relate to the different styles and outlooks of the authors who wrote them. But the point of such a book would boil down to this: these rules were all written by authors after they had already had long experience with the craft of writing.
The rules are a distillation of an author's hard-gained experience. And they are retrospective; the author looks back over his or her own struggle and pulls out things they learned over the years, things that helped them, or disciplines they found fruitful to impose on themselves. None of these authors started with such a list. Or if they did they eventually outgrew it and came up with their own list, which is why all the lists are different. Zadie Smith didn't sit down to write her list in order to repeat what other people had said. She wrote the list because she felt that she could say something no one else had said (something every great writer feels when they sit down to write; and if you've never read her, Zadie Smith is indeed a very good writer).
So, remember this when you feel overwhelmed by lists of rules and tips and advice: All of these rules are useful to follow, but all of them can and have been broken by very good writers, who produced very good writing by doing so.
The trick is that when a good writer breaks one of these rules, they do it in order to accomplish the one thing that all writing absolutely must do: grab your reader's attention and keep it while you impart to them an idea or an emotion. This is the only rule you really need to follow, the "Big Rule", so to speak.
All the other rules are there to help you do this, and they should be followed to the extent that they help you and abandoned when they no longer can. This goes not just for the grand lists mentioned above that deal with how to be A Writer. It also goes for the advice on style that you find in elementary writing manuals: avoid the passive voice, keep your sentences simple, don't split the infinitive. These rules are not final. They serve the Big Rule. Even the rules of grammar are intended to do this, though these particular rules can't really be broken. Still, the only good reason grammatical rules exist is to ensure that people can understand each other, which is really just part of ensuring that the Big Rule can be carried out.
So, how can you gain the kind of skill and experience it takes to know when to break a small rule in favor of the Big Rule?
Well, you can only gain it by writing, by experimenting, by struggling, and by taking risks that may lead to failures. If you feel inclined, go pick up a list of rules. Follow it, but don't assume it fell from heaven. Follow it until it starts to get in the way of your attempt to follow the Big Rule. Then let it go and find another list, paying attention to the writing you produce and to the feedback you get from teachers, friends, or a good writing tutor.
Keep finding and breaking rules until you've discovered a personal set of rules that belong to you and that govern how you express yourself. This list is guaranteed to be a little different from everyone else's, and it will be part of what writers call your "voice". At that point, you can sit down and write your own set of rules, contributing to the time-honored tradition of writing advice that overwhelms and confuses young writers.
And some young writer, just starting out, will follow your rules and be helped for a time. Then they'll work very hard figuring out the proper way to break them
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