... .matched what I expected of myself. Is this positive entitlement?
speaking broadly, "match what i expect of myself" is really at the heart of the matter.
some people expect Cs or Ds of themselves. some expect an A.
sometimes the C or D student will work their butt off for that C or D. one might come to the conclusion its the best they can do, even after they work their butt off. another might conclude "im a C or D student" and there is no point in shooting for more. similarly, for the A student, they may work their butt off for that A, or it may come easily, with very little work, so they conclude there is no reason to put in any more work.
Would it be fair to say that where positive entitlement exists there is no effort? And where it's lacking, things feels hard/unnatural and are a lot of hard work?
now each of those students might be right in their conclusion, and they also might be wrong. the C/D student who works their butt off might ultimately be capable of more once they clear a particular hurdle, or not; the one that believes there is no point might otherwise achieve an A, or not, and the A student who doesnt put more work in may skate by, or not. but each student is doing what they expect of themselves and getting that result.
what id be interested to know is which student feels most fulfilled at the end of the day.
I think I LACK positive entitlement when it comes to money and work and this is something I definitely have to work on to understand and change.
as i read it, i dont hear a lack of positive entitlement. you know your value as a hard worker, and can assess your work as excellent. you believe as a result of that work that youre entitled to share in lifes riches. that is positive entitlement.
where you struggle is that you dont feel entitled "
to take the initiative to share in lifes riches".
and by that, i do not mean you havent worked for it. i mean you dont feel entitled to ask for what you deserve. that does speak to what you do, or do not, expect of yourself. its the difference between self esteem and self efficacy.