Should a person strive to be rather in the box, or out of the box?
Neither. The focus should be on what is necessary, while ensuring that you remain, to a certain extent, “in the box,” because 1) “L’olam y’hei dato shel adam me’urav im habrios” / “Al tifrosh min hatzibbur,” 2) of practical reasons – you don’t want to be
rejected by your society. But so long as you can get away with something, it’s okay (assuming it’s not something you shouldn’t be trying to get away with).
I, for one, cannot stand boxes of any sort. […] But maybe the desire to break free of any is in itself a box?
If you’re influenced by (read as: consume) non-Jewish media,
that may well be. They’re apparently trying to turn out an entire nation of identical anti-authoritarian individualists.
Anyway, if you’re bored, leave the CR alone and go watch Maru the cat, or some unboxing videos. Maybe you’ll learn to like boxes! But not as much as Maru 🙂