Ren'Py specific questions should be posted in the Ren'Py Questions and Annoucements forum, not here.
If it matters, I'm working all by myself (I'll keep the project small, don't worry) so I won't need to communicate plans or changes to anyone else.
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but improvising is fun. sometimes I find a middle ground where I know where I want to take the story, but I don't know how. so I start scripting from there and end up editing a whole lot. writing interactive fiction isn't that different from writing static prose. that's to say, it's got the same pitfalls and obstacles. if you know what method best works for you, I think it's safe to say it'll work for VN writing.
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This outline will help you prevent a lot of problems that many writers around here face. For example the problem that warmsundae mentioned about making too many story branches can be sifted out this way. If you get bored of writing out all the branches or lose oversight when writing the outline, multiply that by a hundred for the story and you'll know it needs to be trimmed down hard. Another thing you'll do in the outline is keeping track of your assets. In the outline, when there are no full scenes written out yet, you can add characters where they're needed but also easily add these characters to previous scenes to support their existence or scrap a character that doesn't actually have a purpose in the end, before you write the first scene involving them. You can keep the amount of sprites down, make quick assessments how to keep the backgrounds and CGs at a minimum, and put everything in comprehensible numbers at a point where you know whether you can actually make that many assets.
Once you've got your outline, look at how many parts of the story you're rather inspirationless. That thing I mentioned before with the 'insert development here' is a lot more common and a lot more problematic than you think. Getting a good ending or a good plot in the main events is easy for many, getting good pacing and development in between those scenes is only the harder. A lot of people can write something awesome only to find out they have no idea how to mend all the loose scenes together in a proper story.
Once you've got your outline, and it looks like a proper story without chronological holes, you can start writing and once you start writing you can start breaking your own rules. Be sure to go over the change and their consequences in your head, but at this point feel free to write naturally. You know where your story has to go, what the path is, so if a better idea comes up that works with the current, add it.
I myself wrote a 44 page outline for my current project (don't worry, that's a bit overkill, shorter will do to, just make sure not to make it a rushed farce of a summary that won't actually help you at all.) and while writing the story I diverged from that outline quite a bit. The base blueprints are still there, especially the scene plan to make sure that the routes don't all have different lengths is important, but within that outline I can change a lot to my own preference.
Want some CC sprites?
Now I'm more of a planner, and it has worked pretty well for me so far. I still leave some room for random ideas, but I make sure they fit the outline I came up with and have purpose.
I read a book about storytelling/planning, and the author said that you don't even need to follow the traditional plot structure. But if you don't follow it, everything important that happens/appears in your story should happen/appear at least three times in some fashion. It's how characters develop, how concepts get meaning.
It's also great for foreshadowing. I guess you can't do that kind of stuff if you don't plan ahead!
I don't think you have to plan everything down to every little detail or choice, but you should have a good idea of the direction you're leading the reader at all times.
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It's quite easy to create multiple branches, but then you'll have to check the cause-and-effect; do character know about something? Was it in branch A or B? etc.
Generally, look for plotholes in story.
And also there's something many writers forget (and so did I with my first game) - writing is cheap, but adding art to it, isn't.
You can easily set the scenes wherever you want, you can add as many characters as you want... But then you might realize it might be too much.
Every background art, every CG and every sprite set costs both time and money.
So you either plan it ahead, to not get over that. Or you'll end up butchering your story or going half-way with art. Or both.
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On the opposing side, planning everything and leaving no room for improvisation can be quite stifling, so as Mammon suggested I'd say stick with an outline.
Manipulation Teaser Demo: https://drive.google.com/open?id=0BzJ4E ... zV6TWVaclk
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I second this method. The lack of a detailed outline to go by doesn't suit everyone's tastes, but I like diving into things and letting some elements develop dynamically rather than having everything rigidly laid out; it makes me feel compelled to follow what I've set up for myself even if it doesn't flow as well as it could.
That being said, I think in some particular cases -- for example, mystery stories and rather long games (for me, anything over 150k words) -- having a more solid plan is a wise tactic, no matter how good you are at improvising. Details can always be changed, of course, but most stories stack these details on top of each other from the very beginning in order to form an immersive story and world, and the longer or more intricate your idea is, the more difficult it'll be to change one thing without having a domino effect on the rest of the game.
Writer, Programmer, Designer
If you are going to improvise for your story, then my personal piece of advice is to write down every little thing that happened as you go along. It's easier to keep track of all the events and there's less of a chance of getting mixed up. If you plan, then try to find a flowchart or "web" maker such as draw.io to keep track of your choices. Either way, both options involve writing down your story.
Good luck on your VN!
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Stuff like foreshadowing and/or Chekov's [insert item here] you'll have to fit into the story on the second draft with meticulous care not to break anything or create plot holes.
That said, excessively detailed plans kill the fun of writing, at least for me. So I just imagine really nice and sweet or heartwrenching scenes and write backwards from them. Connecting as I go and leaving hints along the way.
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Once I actually get to writing, things can divert from the outline because now I have a better idea of what I can or cannot do without messing things up.
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