Compassion Vs Tough LoveWhen does compassion give way to tough love? My brother is not so great with his finances--in fact, he's really bad. He makes decent money, but just blows it on who know what (he even admits he doesn't know where it goes). Now he wants me to bail him out, and not for the first time. Part of me wants to help him. I was once a struggling student, and have also suffered from my own financial stupidity. I know how much it sucks to not have any money, to wonder how you're even going to afford gas to get to work the next day, to sit at home skipping meals until your next paycheck. It sucks. Plus, there were a few times when he helped me out (though it's been more often the other way around). So that part of me wants to help him out.

However, another part of me feels like I should just let him suffer for a while and learn from his mistakes. Is it possible he can still learn if I bail him out yet again? He has a decent job and I know he makes enough money to pay all his bills, but he doesn't pay any attention to where his money goes. And now he's in danger of having his gas and electricity shut off. I've told him many times to trade in his SUV for something cheaper (or heck, just drive the beater he has in the garage), but he hems and haws and then doesn't do anything.

I don't know what to do. I told him I'd see what I could do, but that first, he had to write up a budget and email it too me, and check on trading in his truck. I'm not sure it will help. I was hoping he'd see that he really does make enough money if he'd just pay attention to where it goes, but then he admitted he knew that already.

No one could claim I owe this to him (in fact, he probably owes me money). I might even be doing him a favor by saying no. So then why do I feel guilty for even thinking about it?

UPDATE: I had decided to go ahead and send him whatever I could afford (which still wasn't quite what he needed). But then just before I was to head to the post office, he called to say he got a power shut-off notice on his door and his girlfriend saw it before he got home. She went ahead and paid the bill. Hopefully, he'll start being more careful with his money.