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For me, glatt, the feeling bad about being poor comes because there are other people involved. I don't mind making sacrifices myself, and I'm very good at living very cheaply--when I was poor in college I knew it, but like you said, I didn't feel bad about my situation. But when spouses and kids became involved, suddenly I was very aware of how my situation stacked up with the "average" and felt bad about where I was.
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