I document extensively on my blog (linkin my signature) and did plan it out. At first I took pictures every ten pounds down (257, 247, skipped 237 and went to 227, etc) and measurements every time I took pictures, in addition to blogging semi-regularly (sometimes daily, sometimes weekly) about my progress, feelings, and changes.
When I hit Onederland I reset my pictures to be at every new weight decade (199, 189, etc) because it was easier to remember than every 7. I still do my measurements each time, too. When I am maintaining I make other markers, like strength progressions or time spent exercising, to pass time and keep me focused. I also planned out goal presents for each ten pounds gone and that has been lovely.
I'm a documenter and planner, what can I say?