Which parts of a character's plan should be revealed beforehand?
Two characters (one is a PoV character) come up with a plan to break a third out of prison. They succeed, with only minor complications.
If I describe too many details of their plan beforehand, it feels like I'm telling the same story twice. If I don't include enough, it looks like they're making it up as they go along.
What would be a good way to tell which parts of their plan should be described in detail before the actual breakout?
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Always a good idea to state major details once, and never again.
How you are going to present the details is up to you. Which characters matter more? Which ones are not a major part of the plan? What are the possible complications? Your PoV character is going to be telling all this, so keep it constrained to his point of view so you can surprise the reader later. Keep it within the narrative limits of your story, however.
Modify the amount of data you are giving to the reader, and use unreliable narration to your advantage. That way, you can keep suspense without diluting your plot.
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You are absolutely right that we only want to see the plan once. Either we follow the planning in detail or we follow the execution in detail. We do not need to read it twice.
Unless, of course, it all goes horribly wrong from the start so the what happens in the attempted execution is completely different from what was planned. But since in your case it goes off with minor complications, that is not the case for you.
So how do you decide whether to show the planning or the execution. Simple: where is the drama? Creating a plan and executing it are, by themselves, merely technical. Story lies in drama, and drama lies in conflict. Conflict exists either external to the character -- the conspirators argue about how to plan the rescue -- or internally -- the hero wrestles with the danger or the proprietary of pulling off the rescue. So the question becomes, where lies the drama? Where lies the conflict? That is the part you write.
Men harmoniously develop plan to bust friend out of jail and succeed with only minor complications isn't a story. There is no drama in it. If merely physical complications arise, which are easily solved, there is still not much of a story. For a real story, you need moral or psychological complications to arise. Then the question is, where in the physical process of the planning and execution of the jail break do the moral and psychological issues come to a head? Write that bit. They rest is just routine.
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