Well, I happen to like map-painting. Or, more exactly, I usually can't get fired up about going into a game without some idea of what I want to see at the end of it, so just setting up everything to be random tends to be a little discouraging.
I won't lie and say that I don't have ideas on where I want a game to go.
Like, I'm playing a Canada Game right now. I wanted to mind my business for as long as possible. I wanted to wait until Germany was winning the 2WK before I started any kind of war, my hands were full in India and Oceania so my tiny army was already split (54 divisions on the American border, the rest in India holding the Indus River). I was pretty much overextended and I don't even think I was out the 30's yet. Next thing I know, idiot Nat France declared war on the Internationale, Huey Long won the Civil War against Olson and the CSA, and then promptly got couped and executed by Pelley. Pelley then asked for New England and Alaska back, I declined.
Fast forward 3 years, I control all of North America up to Costa Rica, India is completely under the Dominion, I'm island hopping my way through Indonesia on my way to Canberra and almost all of Spain is under the Entente.
The game throws you curve balls sometimes and you have to run with it. I didn't think I'd be playing as the Holy Britannian Empire, but that's how the cards fell. It's a virtue.
Edit:
I didn't plan for any of that, my contigency plan for America was to hunker down behind my forts and hope they didn't kill me too fast. Shit gets crazy sometimes.