I know the origin of that saying - it’s from the tall tales of the Baron of Munchausen and meant to be silly, to be an impossible solution, much like crossing a battlefield (and back) by riding a cannonball. And indeed it was used as such in discourse back then - politicians were accusing their opponents of telling other people to pull etc etc to mean “my opponent’s proposed solutions are bullshit”.
But these days, at least among the US right wing, the meaning has flipped entirely - the poor are “supposed” to pull themselves up and out of poverty by pulling on their metaphorical bootstraps (an act that, I feel moved to remind people, is physically impossible). So who flipped it first and when ? And why did that idiocy spread, or why don’t people keep reminding the chucklefucks using that cliché that they should try it themselves (if they want to land on their ass) ?
(BTW, another saying/pet peeve of mine that’s been flipped is “bad apples”. “Yes these people demonstrably did wrong, but it’s just a few bad apples”. Yes, idiot, it’s that. And the saying is “A few bad apples SPOIL THE WHOLE BUNCH”. Because they teach other apples, and taint all other apples by association. There’s no such thing as “just a few bad apples”. End of pointless ranting against the descriptivist tide.)