I think one of the big barriers to discussion of the topic of being "entitled" is that many people are incorrectly using the term. Being entitled means that you have a right to something. When I pay for a cheeseburger at McDonald's, I am entitled to receive a cheeseburger or get my money refunded.
For some reason, people have taken the word "entitled" and twisted it to mean something like "unwarranted sense of entitlement" - i.e. expecting a right to something they do not deserve a right to - almost the opposite of what the term is supposed to mean.
This has really poisoned discussion about government entitlements, since people view the term "entitlement" as indicating a sense of selfishness, when it is really meant to convey that they are things that are owed to people by law.
I think this has made it more difficult for people to conceptualize the idea of righteous entitlement. From my perspective, I am more concerned about the things that I think people should feel a greater sense of entitlement about, like a transparent government, personal privacy, societal equality, etc.