I think he means in the sense that you are not under obligation to go to school or work. However, it is the case of the grass is always greener on the other side. He thinks you are lucky because you do not have to work or go to school, yet he doesn't see how trapped you are. You might think that he is lucky because he gets the joys of experiencing school/work outside of the home and you dont see how dreading it is.
When I lived at home all I wanted was out, now that I am out, all I want is back in, haha.