Most of my financial ineptness comes from my attitude about money, rather than ignorance or actual deficit in income. The money skills I learned growing up don't work as well now that I have a little discretionary money.

I tell myself that "I deserve XYZ"
I buy smalll things while deliberately not looking at how much they total.
I have a hard time declining invitations for activities I can't afford.
I have a hard time buying gifts on a budget.
I really want to buy luxuries for my relatives and friends. But I've expanded my own standard of living, too. I can't afford to do both at the same level at the same time.

The biggest problem is not looking at the big picture, hardly ever. I don't buy ANYTHING I can't afford. I just can't afford to keep buying ALL of it.