It's rare that I outline anymore, but I should. My current story, I just had a nagging idea and went with it. It's pretty much written itself, which is nice.
For me it varies wildly, depending on what works best for that particular project. I tend to at least do a basic sort of outline for every project though. Recently, I've been doing super long and detailed outlines (multiple outlines at that!) for a current project, and that has been very successful for me so I may just try to start doing that for most of my work from now on, especially if it is going to be the least bit long or complex.
I outline all the time, but it varies in concentration. I like to think I'm an organized person and would like to get my facts straight (about the characters or places) when writing. I'll outline a couple chapters and then later give up and free write. I'm a wishy washy outliner, but I always outline.
I usually outline the characters that are going to be common throughout the story and the main points of what is going to happen in the story. I don't get heavy with the details, but I usually outline the general idea of each chapter.
I tend to do two outlines for the same some story. One which would be the first draft of the outline contains little summaries or ideas for the entire story (or the first handful of chapters - usually ten) and then I make another outline that goes into details about what's going to happen to the characters and what they'll do. And then if I'm lucky, a third outline will appear that's just the first two outlines combined. XD
I really don't outline enough. I do it for a couple of stories. But I tend to just try to wing it. Which is probably why I get stuck most of the time. I'm trying to work on editing, restarting, or just outlining the stories that I do have, though. I wish I was better at that. I just don't quite know how to get past this writer's block or depression or whatever this is that is keeping me from working on my stories.
How do you organize your outlines? Do you outline by each chapter or in general or think up the ending beforehand? Just wonderin'.
Usually, whenever I start a story, I have a rough idea of a beginning and a rough direction that the story will head in. The other little details sort of present themselves as I write, and I only get an idea for an ending quite a way along.
I'm kinda the opposite to you when it comes to planning in that if I plan every single thing meticulously, THAT'S when I get writer's block. I get stuck on what to write because the plot has become 'stale' in my mind. I can't write it with enough conviction or feeling if I've planned everything out beforehand, because I've over-thought it, meaning the character's feelings can't come naturally and 'in the moment'. The best plot twists and most emotional pieces of writing have come from me doing something completely spontaneous. Don't get me wrong, I don't work like that all the time, but when I do, I get amazing results!
For nanowrimo one year, I completely outlined everything for my story, but when I got down to actually writing it, I found it hard to write and go with the basic idea of the outline. For my nanowrimo for last year, I did write an outline, but each description of the chapter contained a few pieces of dialogue or description to put into the chapter, and I like doing that better since I'm not constricted to my outline.
Oh man... my story outlines range from a sentence of dialogue or a simple idea to 10 pages of character notes and detailed scenes. I find I don't get things written with an outline though because once I've outlined everything, I no longer feel like I have to let it out anymore.
My outline tends to be the first chapter and then I get lazy and stop outlining. The only story I actually have a properly fleshed-out outline for is What It Is to Wonder and even then, I'm too lazy to actually write out new chapters. I tend to just wing it, or get a basic plot outline in place. I never put effort into those things, I have better things to do with my time, like playing copious amounts of video games
I can't help but do a basic outline for it all then fill it in slowly to how it pleases me! Like a spider diagram really because of this website, I learnt about realtimeboard.com and it totally helps me out when creating stories!