I am painting a tall house using a 40-foot extension ladder that is composed of two 20-foot sections. So, in its shortest, unextended form, the ladder is 20 feet high.
The problem I'm running into is standing the ladder up. There are other houses on both sides of the house I'm working on, and only about 10 feet of clearance between the houses. As a result, I can't stand up the ladder using the only method I know, which is to lay it on the ground at the base of an exterior wall, then push the base against the bottom of the wall and raise the ladder up rung-by-rung with my arms until it's vertical. I can do this in the back and front of the house, where there is enough clearance to lay the ladder flat on the ground, but not the sides.
Because the ladder is so big, it's also not really possible to stand it up in one location and walk it to where I need, at least not by myself. (And even with two guys, it would be tough, I think; it's a relatively heavy ladder, and you just don't have much leverage at the base of something 20 feet tall.)
Are there any techniques I could use to stand the ladder up on the sides of the house without being able to lay it flat?