Puzzle Complexity

I've likened my writing experience to putting a puzzle together while drawing the picture on the puzzle. I don't know if that paints the picture in your mind that it paints in mine, but let's suffice it to say it's not always easy. Sometimes I have a clear picture of what I'm trying to write, other times I'm kind of lost. But the hardest part is fitting what I've written together. I mean, there are rules for deciding what goes where, but sometimes it's hard to determine what the *best* logical order is, because sometimes subjects are so inter-connected and equally-important.
I think maybe sometimes I make it harder than it should be and I get too focused on details. Maybe it's just because I'm such a perfectionist and I don't want to move on until I've gotten something perfect. However, sometimes I think it is necessary to finish drawing the picture before you start adding shading and details, if you know what I mean. It would be like putting the puzzle together and THEN drawing the picture on it. That would make more sense, wouldn't it?
So I guess all this begs the question, if I know what I'm doing wrong, why don't I fix it? hmmmm good question... I guess it's just one of those habits that's hard to break. Especially since I don't always realize when I'm doing it. Like, I've tried outlining then filling in the outline as I go, but all too quickly I move away from the outline and drift back to my old style (I have an aversion to outlines :( ) and/or else I end up redoing my outline fifty billion times till I hate outlines even more than I did before. And maybe this sounds funny but a lot of times I come up with a good metaphor but when it comes to applying it to my situation, I'm lost. :P
So what about you? Anybody else struggle with this problem? Any ideas on how to overcome this?