Cool post. As I've gotten older I've realized that simple things are sometimes more complicated, that the refinement of the self is an ongoing process, and that there's always another box to get out of. In reference to your idea of the dragon, there's most likely someone who believes you are still in a box, and he's gotten out of your box and is now stuck in a larger box.
In a very practical sense I beliee that the huristics you approach the world with are importants. To use a correct, but simple example, there is a massive difference between the NewYork times and Alex Jones.