I usually write with a detailed outline. I'm anal and I like to know what's going to happen next when I sit to write. The most fun of the writing process to me is coming up with that initial idea, that first hook, and then developing a plot and characters around it. Unfortunately though, once I have the outline, the fun is over and the work begins. I have to sit down and flesh out the one or two sentence -- if that -- description I've written into a bona fide scene. Sometimes it's fun, like when my outline just says, "Life in Bristol" and I figure out how to describe the setting of eighteenth century Bristol while also advancing the plot. Sometimes it's tedious, like when I wrote, "The pirates attack" and now I have to choreograph a battle.
Another problem with the detailed outline is that it's a very constricting way to work. More than once have I found myself getting behind in my outline because I have more to say about a scene than I'd planned for. When that happens, I usually end up adding a chapter, and it's kind of scary to leave the outline and then figure out how to get back to it again. It's also kind of exhilarating though.
Which makes me wonder if I shouldn't just try flying without an outline. Since I set aside the Pirate Novel last fall to concentrate on comics stuff, I've come up with a very cool idea for a modern-setting horror novel. I don't think I'm going to outline it. I know basically what I want it to be and I'm thinking it'll be more fun and liberating to just start writing it without having the plot specifics down; to just develop some characters and start writing about them without knowing exactly what happens next.
I'm going to have to try it if only to see if I like it.