First, I was talking with my mom about a year ago, and she mentioned how she's stopped herself from feeling awkward about her poverty when talking with her sisters (who both married high-earners). I figure, if Mom doesn't have to feel awkward about her poverty, why should I feel awkward about my wealth? I certainly don't feel "better" than her because I have more money!
Second, my beloved 19-year-old cat died this summer, and my bank balance did not help my grief one bit (not that I expected it to). My money also doesn't magically cure my depression just by diving into it Scrooge McDuck-style, nor have I been able to buy my way out of many of the other trials and tribulations of just being human.
Third, I've known too many awesome people of all income levels, and plenty of jerks at all income levels too. Having more money sure hasn't made me more moral, or a better spouse, sister, or daughter. It hasn't made me kinder or more honest. And those are the important things.
So, for the most part, I don't feel awkward about what I have or don't have, because I know it doesn't reflect any of my value as a human being.