Bear with me here because I want to talk about a parallel between a character we hate and a character we love, and I know it's not the same thing in both cases, but also it's kind of hard to explain how it's different.
"He just doesn't believe the ordinary laws apply to him. He really believes they can't touch him, and that if they do he can just shout until they go away."
-- Terry Pratchett, The Truth
He tried hinting that she should obey the unwritten rules of Zoon life and stay afloat, but a hint was to Esk what a mosquito bite was to the average rhino because she was already learning that if you ignore the rules people will, half the time, quietly rewrite them so that they don't apply to you.
-- Terry Pratchett, Equal Rites
So on the one hand we have an entitled person who believes they're better than everyone else, and on the other hand... well no, actually the first hand is both of them.
To be fair Esk is only (almost) nine, and she does learn a little humility in the course of her hero's journey, and in any case her high opinion of herself is objectively justified.
But here's the thing I don't get.
What, fundamentally, is the difference between being arrogant and being assertive? Both involve asking (or telling) people to make a special case for you.
My hypothesis is that it basically comes down to whether you legitimately deserve to be a special case (assertive) or just think you do (arrogant).
It's clear in the books. Esk does. Lord de Worde just thinks he does.
But how can we possibly know this about ourselves, in real life?
I feel like I'm nothing particularly special, so mostly I follow the rules and don't speak up, and that made sense right up until I realized that my child had internalized my worldview. My child (who is obviously the most special person in the universe!) strives for invisibility.
I mean I'm glad they're not an entitled brat, but sometimes they need to advocate for themself, right?
But again, what's the difference between "entitled brat" and "standing up for yourself"?
How do you manage to have enough self-confidence that people don't walk all over you, but not so much that you tread on others?
How do you make sure get your fair share, without being unfair to everyone else?
I don't actually have an answer. If there is one it's probably in the form of a huge decision tree, because in any situation there are many, many factors that go into whether it makes more sense to push for the special thing you want or take what you get and don't throw a fit.
Just, if you only follow one rule, try this one: Be kind. To yourself, and to everyone else, as much as you can. I don't think it's possible to truly be kind and also be an arrogant entitled brat... or invisible.