Oh, I've been involved in a scary experiment.
Usually I outline carefully before I write anything, especially a novel-length piece. For my current WIP, I decided just to plunge in without a plan, in hopes that it would make the main character seem lost and wandering. The first half (30,000 words) went great, but then I just couldn't go on. Of course, it was because I didn't know where the story was headed, or what the point of all of it was. Just wandering only worked for so long. There had to be a goal.
Yesterday I realized it was time to do the old outlining bit. It had never occurred to me before this that I could wing it for the first half and outline the second half, combining the two approaches. I did so, and now I know exactly where I'm going.
I'm not telling my main character yet, though. Don't want to ruin the surprise for him!
How thoroughly do you outline? Have you ever tried to grow a plot organically as you write, without the plotpoints in place?