So here's a question for you: when should you stop being compassionate? Maybe I should rephrase the question. I don't mean to say when should you stop being compassionate, but rather, when should you stop acting on that feeling. Maybe a hypothetical situation will help me clarify. (Please note that I'm making this hypothetical up 100%--it's not one of those "hypothetical" situations. It really is just to illustrate the point.)
Say you have a friend, and your friend is a complete bonehead. He does all sorts of stupid things, regularly. He makes poor financial decisions, poor career choices, poor everything. And he constantly comes to you for help bailing himself out. How many times do you bail him out before you tell him you're not going to bail him out anymore? Let's assume that each time he asks for help, he seems to be really sincere about it. He acknowledges he's screwed up in the past, but he swears those days are over, and this is the last time he'll need your help like this. Except that last time happens multiple times. It never seems to end, and there's no sign that your friend is really learning anything except that you'll be there to bail him out, no matter what.
When do you cut him off? What if he has children? What if they'll suffer for his stupid choices? Do you wait longer to cut him off in that case?
I don't really have an answer here--I'm more just writing this to see what some of you think. There are no doubt cases where situations like this go both ways--some where the friend really does turn his life around and improves, and others where he remains a leech on society and you. I personally think there comes a point where you're no longer helping, you're enabling, and continued bailouts are actually causing problems, not solving them. But where is that line? When do you know you've reached it? And how do you handle the problem of breaking it to your friend that the lifeline is gone? Yes, you can say "this is it," but history has shown he'll still be back asking for help next time, and nothing you've done to that point has given him any reason to doubt he'll be able to weasel the help out of you.
So there you have it. My deep question for you today. Discuss amongst yourselves. Just keep it civil.