TIL “Pull Yourself Up By Your Bootstraps” was originally meant sarcastically, or to suggest an impossible accomplishment, because it is impossible for someone to pull themselves up by their bootstraps
While I don't appreciate the way this phrase is used currently, I'm not sure it is worthwhile getting too deep into it. Meanings change over time like discussed in the "hey" post the other day or more recently with the increased meanings for literally.
Isn't that how it's used now? (Although I wouldn't say "sarcastically" but rather "metaphorically".) I would define it as referring to a task that is very difficult due to a lack of outside support.