I'm trying it myself, just putting things out there and saying "to hell with it" because, ultimately, unshitifying things is Zeno's paradox kind of work; you're never really done. And, really, it's probably better than you think anyway.
I think he's referring to the discrete-motion paradox - that you can never reach the other side of the room because you must first go halfway, and before that you must first go 1/4 of the way, and before that...
It's not the greatest analogy in the world, but it sort of works in that it illustrates the fractal-like nature of bug-squashing.
I'm trying it myself, just putting things out there and saying "to hell with it" because, ultimately, unshitifying things is Zeno's paradox kind of work; you're never really done. And, really, it's probably better than you think anyway.