You have often written things here that point to someone with money who is probably impressed with himself. It fits with what I've experienced many times in life, and is probably inevitable to varying extents: people make a lot money and become desensitized to those who have less, along with acquiring at least a subtle notion that they're just a little bit better than the others. "If you work a little harder, you might be as successful as me. Well, maybe not that successful, but successful. Stop whining, proles!"
I have a beloved family member who divorced and remarried a neurologist and now leads a very different lifestyle. The same phenomenon has happened to her, to a certain extent. You'd have to try really, really hard not to become a little callous.
If your parents could afford to send a kid to college, as my middle class parents could, you also came into life with a head start. Accepting that fact alone will bring a person a bit of humility.