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How much outlining to you all do before writing? I ask because, I really only outline a major idea around every five pages. So is that typical, or too little outlining? 

I feel like this has already been answered several times, and if so then please direct me to that thread. If not, then thanks for the help.

I never outline anything, probably to my detriment. Usually when I come up with a story, I just start writing, not even know where I'm going to finish it off. That way, I'm always eager to write, as I never know what's coming up. Hell, I remember at one point writing Path of Death, ending up with the protagonists besieged in the castle and not knowing how they'd get out of it.

Probably not the best way to write, though, so there's that.

Outlining is flat-out the correct way to write, but it's very hard until you study story structure and learn what events should go where. I like to outline down to the level of individual scenes, although due to time constraints or whatever I don't always end up planning in that much detail before I have to start. You will never write a well constructed story without detailed planning, although doing the outline after an exploratory first draft is also an acceptable (if suboptimal) approach.

I don't write CYOAs, but I imagine planning is even more important for a branching story since there's so much to keep track of.

Well the two sides are there. Follow up question. @Steve24833 What happens when you run into a part of the story where you don't know what to write? 

Another follow up @Axiom You say it's very hard trying to get the story structure perfect. Are you talking about parts of the story between/around/making up the exposition, rising action, climax, etc.? 

Yes. A story needs the right balance of ingredients to work: pacing, tension, plot progression, etc. Studying structure helps you learn how to do these things consistently, but it's too big a topic to get into here. I can recommend books.

Then please do. Well actually, if they are on some kind of online document that would be preferred. I don't really have the money to be buying books on the subject right now. Maybe at a different point in time, so still recommend them. I would just like to study now, rather than in a couple weeks.

There are summaries online, but seriously, this is a complex topic and you'll want to read about it in depth. Anyway, recommendations. Blake Snyder's Save the Cat is the single most useful book on writing I've ever read, and you should read it even if you don't read anything else here. The caveat is that it's intended for Hollywood screenwriting and has a fairly strict plot formula, which can make your writing formulaic and robotic if you misapply it. So when I recommend it, I like to recommend you read conflicting or supplementary opinions as well. Larry Brooks's Story Structure is a pretty good introduction to a basic four-act structure (my favorite variant on the three-act structure) and raises a few useful points that StC doesn't. (While I'm at it, I also like to recommend Self-Editing for Fiction Writers as a good primer for prose mechanics, but that's not really related to our discussion here.)

I'd say the most common structures include three acts, four acts (novels), five acts (Shakespeare plays), six acts (TV dramas), eight sequences (movies), and the fifteen beats (arranged into three acts, although imo it's four) of Blake Snyder's beat sheet. But they're all pretty much the same thing; they just divide the key events up in different ways.

Alright, I've taken note of the books. Thanks again for the advice and recommendations. If you feel like you forgot something then make sure to add it. I want to get as good of a writer as possible, so everything helps.

Oh yeah, now that I'm not even trying to be nice, You dropped your books, nerd! NERD!

It's never happened. I mean, short term yeah, I just go for a walk or listen to music, but I've never actually struggled with it. There always seems to be a natural progression to where the story should go.

Another question. Is it really just a sit down and write whatever feels natural? Or do you give thought (as you do things during the day) to how the story could progress? 

Bit of both. If I've done well creating a world, I can just think of various cool scenes or bits of backstory or character attributes while doing other things, like one of Remnants wiping out Probiscan in a shallow battlefield or a final stand made by an Orc fighting elves, and build it in. Many times, it won't fit, so I won't. I never make a conscious effort to plan ahead, sometimes I just have ideas that I think would be cool, and they form the foundation for me to write on later.

Other times, I just sit down and write, and a scene will end up going a different way than I had planned. A small path becomes it's own, more popular game when I realize I enjoy writing it a lot, a game delves more into mythology or I simply decide the ptah is boring and I don't want to write it, and then cut it.

So it really just depends, huh? Thanks for the answers.

Yep, I think everyone gets those ideas for key setpiece scenes. When I'm brainstorming a project, I write down all of those ideas until I have a good pile of them and a decent idea of what I want the theme or protagonist's character arc to be. Then I take my ideas and organize them into an outline. Using structure makes it really easy to know where certain events go. For example, the all hope is lost moment comes just before the final act and is the low point of the entire story, so if I have a major character death/protagonist having a nervous breakdown/whatever, it usually has to go there. A lot of my rough ideas don't make it into the final outline, but I try to fill as many beats as possible with things I'm excited to write.

I also usually find that a string of setpiece scenes usually doesn't have enough tension or stakes, so I like to examine my outline for ways to raise them, particularly at the midpoint and break into the final act.