Where to draw the guilt line

I tend to feel guilty about every choice I make. While it provides me with extreme empathy, it is more crippling than helpful. Sometimes I probably should feel guilty because my choices are selfish, but since I feel guilty all the time, I am not sure that my conscious is helping me too much.

Two examples of this are hitting me at the exact same time, so my guilt is almost crushing. I am not sleeping well, and I am not thinking very well as evidenced by my disastrous class I taught this morning. What makes it worse it that both "decisions" are money related...basically I have decided I can't pay for things and as a result people in my family are disappointed. Rest assured these things that I have decided not to pay for are not life sustaining...I am not withholding healthcare or food, or even cell phone coverage...

I wonder if my guilt stems from not being able to determine for sure if I am truly unable pay for these things, or I just am not willing to make the necessary sacrifices to pay for these things.

I also then tend to second guess every other thing I spend money on because maybe someone will think I am being frivilous when I could be saving...What makes this even worse, is that it is very likely that I am so self-absorbed that I am convinced my decisions are so shattering, when in reality no one really even cares that much.

P.S. Maybe I will win a cool Post-It notebook that will make me feel better.

P.P.S. I even feel guilty for wanting to win said notebook, because a college kid commented that she was poor and so I should let her have it.

ETA: I refreshed Kat's site constantly after 9pm CST, and fuck if I did NOT win that stupid Post-It Notebook.