To the extent that life is a never-ending poker game with everyone you know, your bank account is your poker hand, and you should never show it, whether it's good, bad or mediocre.
But, like you perhaps, I have more money than some people I know—a financial cushion to in case I get myself shitcanned someday, the beginnings of a college fund for Scout, a prayer for a graceful conclusion to this frenzied life of mine.
You could argue that there's as big a psychological disparity between someone who has a little safety net and someone who has none, and someone who has a vast financial empire, and me.
And you'd be right.
So why don't I keep making preposterous verbal gaffes about my "wealth" (a term, like "slather," that makes me queasy)?
Why don't I say to my truck driver friend, "Why don't you get those teeth fixed?"
Because I hang around the truck driver enough to realize he doesn't have any dental insurance!
Why don't I tell my nurse neighbor that she should encourage her teenager to major in English instead of business?
Because I know the nurse well, and have figured out that she's sending her kid not to a four-year intellectual dreaming range (as my privileged parents did), but to get a degree that's going to secure the kid's financial future.
Why don't I act uncomfortable and weird when someone suggests that, despite my heart-of-gold empathy and general salt-of-the-earthedness, I probably do see things a little differently than someone who has less financial security?
Because I know they're right—because I know people who have tons more financial security than I do, and I know they perceive the world differently than me.
Mitt Romney keeps making these gaffes because he doesn't have real, detailed relationships with people less well off than he is … and none with anyone significantly more well off (because no people exist).
So he's just disoriented in this area and can't figure out what sounds right to regular people, and what sounds like a couple of Cadillacs.
It's that simple.
Now: Does this particular disorientation mean that Mitt Romney shouldn't be president of the United States?
Well, far be it from a rich guy like me to tell you. Or a poor guy ike me to tell Mitt Romney.
But I'll tell you this: The more deeply you understand the people you're communicating with, the better the chance that you might say things that mean something to them.