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There are rules to writing and we often talk about them here. But sometimes a good writer will break the rules. And to be honest some of my favorite pieces of writing are from when this is done well.

So how do we do it well? Is there some way to measure whether our own application of rule-breaking is done well? Or is it a mostly intuitive process?

I am not concerned with the reception of publishers. I am concerned with the reception of readers and the idea of creating good work. I am just interested if there is any type of guideline that can be followed to writing good creative works.

I have heard two rules about this in the past:

• You need to fully understand a rule before you can break it


• Only break one rule at a time

Are there any others? Does it change for rules of grammar as apposed to the rules of style? Are these rules about breaking rules as equally breakable as the rules that are being broken?

I would say that in writing, in particular, we shouldn't break the simple rules of grammar and spelling and many other basics. My reason for that is quite simple, if you writer "gramer, speling, n simpel" most readers (and definitely most agents and publishers) are going to stop reading right there. If your intent is to sell books (as opposed to writing stories for your own private entertainment), then you need to follow the basic rules that make you look like a competent writer in your chosen language.

Now, one of the "rules" in writing is to avoid "-ly" adverbs. Angrily, spitefully, joyfully, quickly, etc. But JK Rowling uses them liberally. (Stephen King says, with joking disapproval, that 'She's never met an adverb she didn't like.')

(The problem is discussed elsewhere on Writers; basically the issue is 'telling' the reader a state of mind instead of 'showing' them a state of mind, and they can feel quickly overdone.)

Breaking that rule might have prevented her from selling her first book more quickly, but eventually it was okay for the lesser literary sophistication of her young-adult audience.

So "no -ly adverbs" is a breakable rule. I think her books would have been better if she'd followed it, but, meh. Her imagination and story line obviously far more than make up for the issue.

Other and bigger such writing rules can be broken. For example, the Three Act Structure was derived from many hundreds of successful stories, and basically the three acts are "the beginning, the middle, and the end". The structure details what is typically IN each of these segments, at least in the majority of popular stories.

But you can break it. Shakespeare uses a Five Act Structure which contains twists in different places, and history suggests that works gangbusters. The "Hero's Journey" is another structure that works great. In the Three Act structure, we typically describe the protagonist's "normal world" first, and have an "inciting incident" at about the 1/8th mark, and we have our protagonist leaving their "normal world" about the 25% mark to deal with a disruptive problem at the end of Act I, and this marks the beginning of Act II.

But those have been severely compressed and expanded in the past. That can happen because a writer is awesome about creating a lot of plausible conflict in a story, and as long as there is something up in the air that readers are thinking about, a writer (like Stephen King) can basically go on indefinitely, because what we are reading is interesting and that carries the day.

That is the one rule you shouldn't break: You can't be boring. If I get tired of reading a scene and put the book down, that may just be me, being cognitively exhausted by my day, or mentally distracted by something else.

But if I'm actually bored with your writing, then after the second try I'm putting it down for good. I think agents feel the same; their professional time is limited, the number of manuscripts they get is more than they can represent, and they are professionals actively looking for reasons to drop a book and start the next one. They don't want to waste time.

They (professional readers like agents and publisher's first readers) are your litmus test. If your writing is interesting to them, and you don't have any (or many) mistakes that would break their reading reverie or make them wonder when you are going to make a point, you don't really have to worry too much about whether you are following the rules.

Remember, the Three Act Structure and other rules are basically derived from the study of successful stories; they are not mandates from on high, but a descriptive science, kind of like primitive chemistry. Because the stories existed long before they were studied to find commonalities, and they were written/told by story-tellers that used trial and error to find structures that kept their audiences captivated.

My advice (as a research scientist) is to learn and follow the rules, but if you have a great idea you believe will still captivate the audience, feel free to break them. But you still have to test if it works, and if you are proven wrong, find another way, or follow the rules.

Elaborating on what a great teacher (Portuguese literature) of mine once said:

1. Rules exist for a reason - understand why

If you know why a rule exists, you know when you should follow it, when you should bend it and when you should break it altogether.

By rules, she meant anything from punctuation and spelling to versification and figures of speech.

Think of it as cooking and eating. There's a rule that white wine goes with fish dishes. You can either follow it dogmatically, or you can understand the reason for that rule: fish tends to have delicate flavours and red wine tends to have stronger flavours that shadow the flavour of the fish. Once you know this, you can choose a stronger flavoured fish and match it with a lighter flavoured red wine. Or you can simply decide to follow it because the taste of the fish you want to eat really is very delicate.

2. Rules are tools - make sure you are the one using them

This expands on the first rule. You shouldn't understand simply one rule, you should strive to learn as many 'rules' as possible (and this means understanding what they do).

Rules are not straight jackets: they are tools that you can choose to use as designed, or which you can decide to use in different ways. Ask not what this rule forces you to do, but what you can do with it. Remember: rules are tools and you are the one who's using them, not the other way around.

Back to pairing wine and food - if you follow the rule dogmatically, you are allowing the rule to dictate your actions and you feel constrained by it. But if you understand the logic behind it, then you choose to either use the rule as is or change it, always for the best effect according to the situation you're facing.

3. Everything an author does has a reason - what is yours?

You already know the rules and what you can get out of them. Now, it's time to ask what you want.

Think of it as a day out. You want to visit this beautiful beach, and you can get there through two different routes. Which one will you choose? It depends. Do you want to get there as fast as possible? Or perhaps you prefer to spend a bit longer but enjoy a more beautiful scenery. Better yet would be to make a slight detour and have a late breakfast at that new restaurant north of the beach.

Do the same with the rules: What is the effect you want? Then look at the rules-tools at your service and choose the one or ones that serve your purpose, and then use them as is or change them.

Remember! Limits can either smother or inspire

While studying literature of the Barroque period, my teacher insisted on this idea. If one has no limits, one can do whatever. There is no pressing need to innovate because anything goes. But when there are limits, then one can either allow the mind to be smothered and dogmatically follow them, or one can let them sharpen the mind and imagination to overcome those limits without breaking them.

Imagine you're told you cannot mention a certain topic. How can you mention it without breaking the rule? That's what artists did during censorship periods. It does sharpen one's creativity to be pushed into finding ways to circumvent limitations.

The same thing happens with rules: you can let them smother you (ie. they're using you) or you can let them sharpen your mind (ie. use them to fit your purposes).

Anyone can be a master following rules dogmatically, because those rules will safely guide you away from pitfalls. To be a genius, though, you must know the rules so well, that you know when to change them and still avoid the pitfalls.

If one doesn't yet understand all the rules-tools at their disposal, then one must be careful when bending and breaking them. Whenever you feel a rule is smothering you, stop and understand why the rule exists, what pitfall it keeps you from falling into. Then see how you can twist it without falling into said pitfall. Keep your aim in mind and look carefully at the end result to see if it is working.

Neil Gaiman, making a commencement speech in the University of the Arts in 2012, said the following:

When you start out on a career in the arts you have no idea what you are doing.

This is great. People who know what they are doing know the rules, and know what is possible and impossible. You do not. And you should not. The rules on what is possible and impossible in the arts were made by people who had not tested the bounds of the possible by going beyond them. And you can.

If you don't know it's impossible, it's easier to do. And because nobody's done it before, they haven't made up rules to stop anyone doing that again, yet. (source)

Forget the rules. Don't worry about breaking them or not breaking them - forget them, and go test the limits of the possible.

"Is there some way to measure whether our own application of rule-breaking is done well?"

Yes, that tool is called readers. Give your writing to a number of critical readers and see what they say.