Of course, the Problem with a capital P is that John is actually a clueless, physically awkward dolt with an overweening addiction to shortcuts that make his life worse. It is the English genius to be smugly proud of the sort of moronic cock-up that cannot be in his best interests that John sees as a master-stroke of practicality. There used to be a British sitcom called 'Last of the Summer Wine' that celebrated the tendency of deluded, self-important nincompoops like John to have grand visions of success that, well, fall to itty bitty bits when colliding with the laws of physics and probability.
The reason that he never learns not to do stupid things or take idiotic short-cuts comes from not only not having the sense to understand what he did wrong but also from the sort of mutton-headed pride that views having his son know that he used to be a kid like himself once as a horrible humiliation. John can't admit that he's a thumb-fingered imbecile that swamps canoes, gets stuck in dumpsters and makes windy noise about highway exits because he's too stupid to know what he's bad at because doing so would force him to realize that his self-image is wrong.