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had a conversation with my mom the other day where i said something like "I'm so awful at writing these college essays haha" which is something anyone in my generation would find normal (as we also tell each other how much we all want to die), but my mom reacted very negatively and i realized she wasn't used to self-deprecating humour and she also stresses maintaining a facade of confidence and ability.
I don't see how that was humour though, that just sounded like you were putting yourself down, which is indeed bad for your confidence.
It's a huge generalisation to say that older people are incapable of trying to find humour in their failings. I do it all the time, and I'm probably about three times your age.
Still, I somewhat agree with what your mother said: presenting a positive and confident image can get you far. She (presumably) cares about you and wants to see you do well, so it makes sense that she would encourage you to behave like this.
You'll probably find as you go through life that an awful lot of people are faking it in the hope of eventually making it. If you assume that most people aren't actually evil, that explains a lot of the stupid, fucked up things we see happening in the world.
There are those who are so full of self-confidence that they truly believe that they're fantastic because they're so ignorant and self-deluded that they're incapable of understanding just how crap they are. At the other side of that spectrum, there's something called the Imposter Syndrome where someone who's actually competent believes that they aren't. Partly, that's a sign of a general lack of self-esteem, but it's also the case that the more you know about something, the better you understand how much you _don't_ know.
It can be a tricky line to walk, but you should try to present a positive, self-confident image (even if it sometimes feels like you're playing a role in a play), while also being very careful not to try to bullshit people about your abilities and competence.
It can also vary depending on where you live. I'm English so I often use this kind of humour and I find in some cultures it really confuses people and they start telling you that you should have more confidence in yourself.
It’s stupid as fuck when younger people think they invented shit. No, satire and self deprecation have existed since humans have had brains. I’d say it was more prevalent in the 70’s than it is now from what I’ve seen, considering a lot of times now you say something jokey and people get all fucking concerned. But apparently ur kinda fucking stupid. And that’s hardly a joke lol