As an obsessive timeliner, I can genuinely say *do not try it*.
Hmm. While I never wrote an overall outline for my novel-in-progress (I basically just let it write itself), I did, practically from day one, develop a timeline for it, and for all the short stories that have spun off from it, in order to make sure everything in the milieu lines up with everything else in it, and that all the technology and pop-culture references are completely air-tight.