For me, this always becomes a topic with almost endless permutations. However, if we are going to explore true freedom, it seems to me that the dialogue might start with removing the obsessive (and often blind) "more" from our vocabulary and instead comtemplating the word "enough" more.
A brief story: Many years ago I had an import and retail business; it ended up doing fairly well. I was approached several times about expanding to multiple locations and franchising. The fact that I was "not interested" because I was making "a comfortable living" (about $80K, at the time) got me labeled as an underachiever and almost as a "slacker." For a couple of people, I was almost "unpatriotic" because I didn't "worship at the altar of greed;" I was satisfied.
So, I believe we need to change our social vocabulary and remove the "more" paradigm before we can become free. Why? In a world driven by "more" there will always be "less," and that means "fear of scarcity." And when we fear scarcity, we remain slaves to the "More Machine."