I've been at my job for over six months now. I'm feeling totally comfortable with everything, so I figured it's time to do some scheming to start working from home part time. For Phase I of my plan, I told my boss that I'm setting up a workstation at my house for those winter days when kids are home sick from school or the weather is bad. He was like, "Aww, yeah, dude. I'm all about working from home." (He does himself a fair amount.) "What do you need? Docking station, monitors? I'll get those ordered." Apparently, there is neither a need for me to go to the store this time nor for any additional phases to my plan.
My job is so insanely cushy that part of the reason I want to work from home is to see if I can pull off working another job remote. Full time, part time, permanent, contract, whatever. I figure, even if I only last a couple of months, that'll be a shitload of extra money to have without much difficulty.