Most writers have mixed feelings about the value of outlining. Many will argue that an outline is best after you’ve completed a first draft and explored your ideas for characterization, plot and scope of your novel or story. An outline, they argue, will stunt creativity, even if you have to throw out 3/4 of what you wrote before the outline. Other writers argue that an outline is the only way to effectively structure a long work without degenerating into broken and unresolved plots or a monsterous multi-plotted work. An outline is a way to structure the bones of your work, so the flesh can be built around it.
I fall into both catergories. On shorter works I make sure to have a general idea of characters, basic conflict and what I’d like to see happen but I don’t outline much beyond that. With longer works I start out writing without an outline, getting a feel for characters and interactions. Much of that will end up in the delete trashcan, of course, but it gives me an idea for what works and what doesn’t. Then I try to make sure to have a general outline for the mechanics of the world I’m working in (for sci-fi and fantasy) and as much of a general outline of major plots as I can. Now it may be possible to come up with a chapter by chapter outline early on in your writing, but I find keeping a working outline that expands and changes as the writing goes on is most feasible. Having a goal to work towards in the next session eliminates frustration, alleviates writer’s block and makes your writing time more productive.