I've mentioned before I have a somewhat antagonistic relationship with regards to outlining.
Too little detail, I'm pantsing. I'm not a pantser, really. At least not in the medium to long run. Writing without a plan leads to bloviation. Bloviation leads to pain. Pain leads to, uh, something that hurts. And that leads to moral laxitude, which leads to, fuck, I don't know. Jerry Falwell. And that means hookers. Can't have that. Wait. What was I talking about?
With too much detail I get bored because it feels like everything's written out already. When I go to write, I have a strong feeling of "why bother, I'll just have people read the damn outline". Then I go off and play Minecraft. It's all written down, there's nothing to surprise me, it's all a slog.
There were some things which still didn't make sense by Sunday, so I decided to spend some quality time re-outlining. In this case, I moved the outline into meatspace. I grabbed several blank sheets of paper and some markers and sketched everything out by hand until I had a good grasp on how this first section should hang together efficiently.
This is a trick I've used often in the past--sometimes there's absolutely no substitute for the tactile nature of just grabbing a pen and drawing shit out. Actually arranging everything in physical space, drawing lines and arrows...it engages more than one sense and pulls stuff out of your subconscious which would never come out and play if you were banging keys on a laptop. If you have any holes in your structure, they become readily apparent once you've sketched things out.
By the time I finish writing something longer, it often looks like a ticker tape parade had stormed through my working area. I'll have sheets on the floor and every other horizontal surface available to me. If I have whiteboards or chalkboards handy, I'll use those, too. It's the sort of thing that Hollywood directors would use to show I was either a mad scientist or a serial killer. The next scene of the film of my life would probably involve mashed potato sculptures or dead prostitutes.
It works for me (the outlines, not the dead prostitutes). I usually only do it when I'm having a hard time visualizing something or I have to get something done, but I'm not quite sure which approach would be the most efficient. The end result is spectacularly weird when I'm working on a difficult bit of code. With fiction, somewhat less so, unless you actually read some of the words and sentence fragments.
But now I'm finally at the point where I have to transform some of this wreckage into words and because of the level of preparation, it's somewhat frightening and confining. We'll see what happens.