I'm a big fan of outlining. Here's the theory: If I outline, then I can see the mistakes I'm liable to make. They come out more clearly in the outline than they do in the pages.
Sentiment: NEGATIVE
The benefit of this kind of outlining is that you discover a story's flaws before you invest a lot of time writing the first draft, and it's almost impossible to get stuck at a difficult chapter, because you've already done the work to push through those kinds of blocks.
If you do outline, you have to be aware of the problems that that kind of thing can cause.
I'm a great believer in outlines.
I used to be an obsessive outliner - figuring that writing without an outline was like jumping off a cliff and building a parachute on the way down.
I outline fairly extensively because I'm usually dealing with real events. I don't need to give myself as much information as I used to, but I still like to have two pages of outline for every projected 100 pages of manuscript.
I am a big proponent of writing a great outline. That way you can avoid hitting a roadblock. There is no worse feeling than writing yourself into a corner but if you've figured it all out in the outline then you won't have that problem.
I do not outline. There are writers I know and count as my friends who certainly do it the other way, but for me, part of the adventure is not knowing how it's going to turn out.
In my stand-up, I generally improvise from an outline.
I don't like outlining, because books are organic things. Sometimes a book doesn't want to be written in a certain way.
Outlining is like putting on training wheels. It gives me the courage to write, but we always go off the outline.