My boss asked me to address a gutter issue on the second story of a building I help maintain. I'm basically a grounds keeper of sort, a janitor, gardener, light maintenance, with a contract.

He advised that I purchase a ladder that can reach the height. I've yet to measure the height but I'm guessing I'll need to buy the max length of ladder (40ft). I advised we get a contractor (gutter cleaners) to do the job but he for some reason told that I must do it. I even offered to pay for it since if it's something I ought to be able to do because I must do, I should pay for it. I don't feel safe doing it because it's not something I've done. I also fell off a ladder once down a set of stairs in which I could've killed myself.

So I'm guessing I'll still pursue a contractor even though my boss said that is something he doesn't want in order to fix the problem.