The message is a bad one. A little girl's fantasy about being a princess has nothing to do with a sense of entitlement or the idea that she's going to lie around on silk cushions all day ordering people around, and it has even less to do with inner-city entitlement.
When a five-year-old girl says she wants to be a princess when she grows up, she's not talking about some adult image of a princess shaped by history and politics, or even by images of Princess Diana and the Duchess of Cambridge. She is referring to Disney heroines, who are the only princesses she sees regularly.
She means she wants to be beautiful and feminine, like Disney princesses, with long thick hair and gorgeous gowns.
She means that she wants to be spirited and independent, engaging in risky but ultimately triumphant adventures, as Disney princesses do.
She means she wants power, which is something little girls do not have.
She means she wants love and marriage.
There is not one thing in this list of dreams that is in conflict with conservative goals or principles. They're normal female psychological desires, and are not to be discouraged. What has to change as the child matures is her idea of how she is to get these things. Since she's not going to get the gowns, carriage, and loving husband by inheritance, she's going to have to work for them, one way or another. That could mean having a job, starting a business, or just being such a wonderful, loving conservative woman that some fine man will want her to be his wife and the mother of his children.
But to have a homely middle-aged woman dressed in black, a woman who never had that handsome prince, nag little girls about choosing an appropriate career path is disturbing. Do we have to start the pressure in the Sesame Street years? Can't kids go through childhood unencumbered by worries about their careers? The continual drumbeat to Have a career, Work, Perform, Dedicate, Work more, Sacrifice conflicts with the traditionalist belief that it's fine for a woman to be a wife and mother caring for her children.