Well to use your diet example, the way I see it is you feel ok about eating the cupcake because you didn't eat the candy bar, right? And that's easy to measure because it happens in a short space of time. So what if you record all your theoretical savings and then, at the end of the month maybe, spend a portion of those savings? That's what I do because, as a student, I always feel guilty about spending money but if i know that I resisted, say, buying Angel Season 5 for £40 I can feel ok about spending £15 on Firefly instead.
The way we handled it when we were still being good about budgeting was to have a spending allowance just like the grocery allowance, so there was a certain amount of cash per week allowed for eating out or entertainment. If you wanted to do something big, you had to resist something small.
Well, assuming you're talking about $100 in general and not an actual $100 bill, you *could* for example take out the $20 you would have spent on the DVD, or better, a token amount of the money (10%?) and put it in the shoebox instead of the envelopes. Whenever you deny yourself something that you want that strongly, sock away the money, and at the end of the week/month/whatever, take out the money you "saved" and treat yourself to somethng you really want and/or earmark it as your Rainy Day Fund and thus have spare funds on hand for dinner out or something.
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This worked out fairly well.
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