Last Friday’s question about the moral implications of spending prompted a great discussion, as well as a few personal messages. One of those e-mails was from Dave, who wrote with his own ethical dilemma. Instead of looking at the world at large, Dave wants to know how to handle a financial dilemma closer to home: with his own family. Here’s his story:

I read your site though I no longer need it. I did a lot of the things you talk about and was able to retire early because of it. The rest of my family hasn’t been as smart or lucky. My sister is doing okay, I guess, but my brother is in a lot of trouble, and my parents aren’t anywhere near ready for retirement.

My brother and his wife have two kids. They declared bankruptcy a couple of years ago and have tried to make a fresh start. Life has dealt them some bad blows, but they’re doing nothing to protect themselves either. To be honest, I feel like they just set themselves up for trouble. After declaring bankruptcy, they just returned to their former lifestyle and now they’re back in debt again.

I could help my brother but I don’t know if I should. (Plus I don’t know if I even want to, which makes me feel like a jerk.) What if I loan him $10,000 (or give him the money)? That might solve the immediate crisis, but what does it help long term?

My parents have problems too. They don’t spend a lot, I guess, but they hardly have anything saved for retirement, and they should both be retiring in a few years. I think they have maybe $20,000 total in a savings account, and maybe the same in various retirement plans. They don’t spend a lot, but still $40,000 won’t last long.

I guess I’m wondering: What’s my financial obligation to my family? I could bail them out, but I feel like that won’t solve any of the problems. Should I do it anyway? How? I don’t want my brother and his family to be living on the streets and I don’t want to see my parents eating dog food, but I find it difficult to help them when they won’t even help themselves. What are my responsibilities here?

I sympathize with Dave. I’m not as well of as he is, but I sometimes wonder what my obligation to my own family is. Like Dave, I have a brother who has really struggled with his finances over the past few years. Some of this is because bad things have happened to him, but a lot of it stems from his choices. And he just seems to keep making the same poor choices, even when I offer suggestions on how he might help himself.

Family issues like this are a perfect example of how money is more about mind than it is about math. It’s tough to make an objective, logical decision about how to help your brother or your parents. There’s just too much other baggage involved.

In my case, I’m not willing to loan my brother money. Though it sounds harsh, I don’t think he’d ever repay it. (And yes, I know that when you lend money to family and friends, it’s often best to view the loan as a gift instead. I’m not even willing to do that, though.) Plus, I don’t think my brother has actually reached a point where he’s ready to make the changes he needs to in order to take control of his finances. He’d rather spend money he doesn’t have to look like he has it than to cut back for a few years and live with less so that he can have more in the future. In other words, he’s not willing to make sacrifices today in order to have a better tomorrow. And that’s what getting rich slowly is all about.

So, I don’t actually have any constructive advice for Dave. I’m in the same boat, though on a smaller scale. Like Dave, I can’t figure out what my financial obligations are in this situation. Can you?

When your siblings get into financial trouble, what are your responsibilities? What about your parents? Have you bailed out a family member before? How did that work? Can you give tips on what went right, as well as offer suggestions on what you would not do in the future? And if you’ve never had to face a situation like this, how do you think you’d handle it? Help Dave (and me) figure out how we can steer our family in the right direction.

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