Here's "My Share"

A friend of mine has a sister who has been broke for years. Ten years ago he got heartsick over watching her struggle while his own career took off, so he began supporting her by supplementing her small income with his own money. He makes $300, 000 a year and gives her $30, 000 a year to help her out. This comes to roughly 20% of his take-home income after all of his taxes (federal, state, local) are taken out of his paycheck.

Now, in those ten years of supporting her, she has not used that money as a foundation to build herself a better more independent life contructed on sound financial footing. If anything, her situation now is even worse than it was a decade ago because she continues to make bad decisions.

She married an alcoholic husband (despite warnings from her family) and she then had a child with that husband who is now estranged, voluntarily putting exponentially more strain on her already stressful life. As of now, despite my friend having willingly given her $300,000 over ten years – money he could have put towards his kid’s college education, paying off his mortgage, or just socked away in the bank for a rainy day – she is no better off because the way she is running her affairs is still a disaster. She hasn’t learned a thing.

Still, he continues to pay her because he believes it is his moral obligation to give back to those in need, especially as he has done so well in life. He’s not thrilled about it, but he gets the concept and bucks up. Plus he genuinely cares for the down-trodden, realizing that a few bad decisions in his own life, a wrong fork in the road taken, and he could have been there with her. He made need help himself someday. Who knows what the future holds?

Now, the other day she came to him for her annual $30,000. But this time, because of new credit card debts accumulated, she asked him for $35,000. Her logic? He can afford it and she needs it.

But he balked at the increase. Her friends (who are also dependent on their siblings) rallied around her and called her “rich” brother selfish and “a whiner.” Awww, they mocked, poor rich guy brother has to pay an extra $5,000 more when he makes $300,000 a year. (This sarcasm was accompanied by fake violin motions.)

But here is his point: can he afford to pay more? Sure he can. Although he will then not have that money to do something fun with his own family, his quality of life will not be noticeably impacted. BUT, the bigger question isn’t whether he could pay her more, but whether he should have to pay her more.

After ten years and transferring $300,000 of his wealth to her, the very situation he’d hoped his income would go to improve has only gotten worse. The reason isn’t because his sister doesn’t have an income but rather she is incompetent with the money she does receive. She is, in fact, incapable of making proper decisions with her finances and indeed her life choices, no matter how much cash she receives.

The brother has reluctantly concluded that if he gives her 35k next year she’ll turn around and spend 40k. If he gives her 40k, she’ll spend 50k, etc. It will never end without her being first forced to work within her existing budget, even it means taking some pain. Let me be clear, if he thought it would do good, if he thought she would spend his money wisely to improve her life, he’d gladly give her twice as much if not more so because he can "afford" it. But he knows from her past that the more he gives her, the more she’ll waste.

So he prefers to keep his contribution at 30k and decide for himself how the 5k more she demands of him can best be put to use in his own life, or even for the greater good if he chooses to give it to a charity he knows from research will used it to make a real difference. For this he is labeled selfish. Go figure.

Does this mean he would ever cut her off cold regardless of his frustration over her profligate spending and/or mismanagement of his money? Of course not. That would be downright cruel and he knows that without his supplemental income she would spiral into destitution. He cares too much to see that happen so long as he has the means to help prevent it.

But, he does feel that he should have a say in how much she needs and should demand to see real progress and discipline on her part before giving her yet more of his income without being ridiculed as selfish or worse. These labels are usually hurled by either the guilt-ridden super-rich who could live the lives of sultans on just a sliver of their net worth or by those who are bitter towards his modest success and feel his sister deserves whatever she can squeeze from him as a matter of social "justice."

So I ask all those who are so pious and so discerning as to what he can “afford” to pay: is that brother selfish for not wanting to pay his sister more than he has been doing already? Or does he simply understand that to pay his sister more is to just throw even a large portion of his good hard-earned income down a bottomless hole with no prospect of it improving her deplorable state without her first dramatically changing her ways?

And who do you think is a better judge as to how his money can be put towards more productive ends: his sister or him? Finally, who really has the moral high ground here?