[Henchman21]

IMO the "bootstraps" thing was always an insulting joke. Something the wealthy would say to knowingly insult the poor. Go do the impossible you stupid poor person while they laugh so hard their monocles fall into their brandy. Its like spitting on someone just cause you can. Yes, this is an absurd characterization, an almost cartoonish villain trope. It's a silly world!

But something happened: people who didn't understand it was meant to indicate somthing impossible started using it like it was some moralizing good. And here we are, saying dumb shit on the internets.

[SR2Z]

The point is the saying is that it's not physically possible to pull yourself up by your bootstraps. It's always very funny when people say it as if it means the opposite.