The only problem I ever have in life.

Damn, that sucks.

I went from plenty of money to no money. What little money I had left, i thought I had more of...

If you're finding that that is always your problem, then I'd seriously think about getting rid of your bit of plastic. Using a card separates you from the money and makes you spend more because you don't actually think about how much you've got left. You're still young (I'm 18 and I've just got my first Debit Card, but the account is for my student loan and won't be in use until October), so what makes you really need a card? My advice would be to pay only in cash - the only thing you use your card for is to get money out of an ATM. Yes, you do lose the simplicity of just walking into a shop, handing them the plastic and walking out, but it means that you'll have a tighter control on your money, and maybe even teach you to handle it better.

Saying that, though, I do fault Sears for not paying you promptly, but you should never trust that something has happened without checking first.

Either way, I hope your financial situation gets better for you.