It was supposed to be sarcastic, and was deliberately referring to something impossible. The sarcasm has been lost along the way. The phrase originally meant “to try to do something completely absurd / impossible”. That makes much more sense!
>“It’s hard to explain why the meaning of an expression changes over time. Sometimes things start off as having a kind of ironic or humorous edge to them, but that gets forgotten along the way,” Zimmer explained. “People have been referring to bootstraps in this metaphorical way for so long, the original irony of the expression was lost. Nobody’s thinking of the impossible image of pulling themselves over a fence.”
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>“Maybe that says something about Americans and how they view themselves,” he added. “That something that seems utterly ludicrous and impossible becomes a regular idiom for improving yourself.”
[https://www.huffpost.com/entry/pull-yourself-up-by-your-bootstraps-nonsense_n_5b1ed024e4b0bbb7a0e037d4](https://www.huffpost.com/entry/pull-yourself-up-by-your-bootstraps-nonsense_n_5b1ed024e4b0bbb7a0e037d4)
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