I’ve literally never understood the expression “pull yourself up by your bootstraps.”

If you did that wouldn’t you just fall flat on your ass? Ow.

You understand it correctly, actually! It’s meant to be an impossible thing. People who say it as something you *should* be able to do are using it backwards. It’s supposed to be something like “That’s impossible. You might as well ask them to pull themselves up by their own bootstraps.”

THAT MAKES A LOT MORE SENSE

I found a neat article!