My series answering the New York Times’ Ethicist column with an active, leadership approach instead of an analytical, philosophical perspective continues with “Can I Turn Down Family Requests for Money?”.

My family splits into two camps: people who have money and people who don’t. We didn’t start in different places; we evolved into them. My father, my brother and I are savers and planners. My sister, my aunt and my mother received the same inheritances, the same educational opportunities and the same career options, but they have spent everything they have and more. My mother and sister each filed for bankruptcy (my mother passed away with more than $1 million in debt).

My aunt is hanging by a thread.

The question is how to deal with the desperate requests for money. I love my family, and it is extremely painful to see them suffer, but at the same time it is difficult for me to fund their lifestyles when they seem like a bottomless pit. I feel guilty and uncomfortable, but also angry and annoyed. Yet how can I watch my sister be thrown out of her house and potentially end up homeless if I have the resources to help her? This will only get worse once my father passes away, as my brother and I will be left without a buffer when the requests for cash come in. I don’t know how to reconcile this. Name Withheld

My response: “The question is how to deal with the desperate requests for money.” I read this question as how to lead them.

But first, besides the problem you describe, you say you feel guilty/anxious/angry/other emotion you don’t like. You can manage your emotional response—through, for example, choosing your environment, beliefs, and behavior—and I’ve never seen a benefit to suffering or being miserable. I recommend developing the emotional skills to manage your emotions. You’ll make yourself more effective in achieving your goals and feel emotions you prefer, which I call a better life.

You’re asking how to lead people, meaning you want to improve your leadership. If you’ll allow me a quick analogy, if you want to learn to create art, taking academic classes in art appreciation may help you appreciate art others made but not to create it. You have to practice, starting with the basics.

Nearly every resource I’ve seen on leadership is leadership appreciation—that is, books on principles and such that help you appreciate others’ leadership but not to lead. To learn to lead you have to practice, starting with basics.

To answer your question on how to lead people, I recommend my book, Leadership Step by Step, which gives you exercises to practice the skills of leadership, not just to appreciate others’ practice. You have to do the work of the exercises, not just passively read it, but what expressive or performance-based practice can you learn without work?

I’m not just plugging my book. I wrote it because nothing existed to give you experience and skills, not just appreciation.

Unit 4 covers what you want, though I’d start at the beginning and do the exercises in order.

The New York Times response:Everyone knows the Aesop’s fable about the profligate grasshopper and the provident ant. Over the centuries, various writers have played with the trope, unsettling its easy moralism: the ant can seem meanspirited, the grasshopper the sort of free-spirited artist who enriches our world in nonmaterial ways. Suffice it to say that you can’t treat your sister the way the ant treated the grasshopper when winter arrived and the long-limbed creature came abegging. But you can help her prepare for the winter to come.

The most useful thing you could do is to try to help her acquire the advantages of the ant’s skill in planning. Your letter suggests she won’t do this on her own, so you’ll need to do the planning with her. (The same applies to your aunt, I expect.) Tell her how you see her situation and discuss it with her, your brother and your father. Assuming your father is going to have resources to leave, you should discuss what her share should be, perhaps bearing in mind her greater need, and putting her share into a trust whose capital she can’t spend down, ensuring that she has some regular annuity as a cushion. If she’s still able to work, getting her to focus on a realistic sense of her constraints may help her see that she’ll need to put away savings of her own.

Given the circumstances and the personalities involved, of course, it may be that none of these measures will help much. So the most important thing you and your brother can do is to be clear with her about what you are and are not willing to do if her grasshopper behavior brings her into financial difficulties. And that means first being clear about this matter yourself. Bear in mind that you owe more to family members than you do to strangers, but you don’t owe it to them to abandon all your hard-earned plans in order to pay for their mistakes.

---

I worked for a company in the finance department. I know that they violated labor wage laws and under-reported wages for workers’ compensation purposes. I pay the taxes that I’m legally required to pay, but I feel I helped perpetrate a fraud so my ex-boss could underpay his. Should I report this company to the authorities? Name Withheld

My response: “Should I . . .?” … Asking what you should do makes sense for children asking their parents. For an adult, it looks like asking someone else to take responsibility, which I call juvenile. Asking for options or views you might have missed makes sense, but you didn’t ask that.

What should you do? I recommend:

1. Figuring out what resources you have—relationships, time, etc
2. Figuring what skills you have and can create
3. Creating as many options as you can
4. Considering what outcomes each option will result in
5. Choosing which option to act on based on those outcomes, evaluating them using empathy
6. Implement the option you like most
7. Do the best you can, knowing that problems will arise

The New York Times response:First, a few practical concerns. One question you’ll want to settle is whether you are yourself liable for filing deceptive paperwork. If you might be, you’d be well advised to talk to a lawyer. You will also need to face the fact that people known to be whistle-blowers can pay a social penalty and may have a hard time finding future employment. That could be a reason to see if you can make your report anonymous.

As an ethical matter, you shouldn’t have abetted this fraud, but the greater responsibility obviously falls on your boss. Filing false information in this way is not just unfair to honest taxpayers; it’s unfair to the employees as well, because getting full workers’ compensation for lost wages depends on a proper reporting of their incomes. So I hope you proceed. Obligations of confidentiality to your employer don’t include the duty to conceal fraud.

---

I was in the food court of my local mall reading a book. At the table behind me was a man in his late 30s. He was seated next to a girl who was about 12. Their chairs were side by side, and the man had his arm around the girl and was running his hand through her hair as if they were lovers — caressing, twirling and playing with it. At one point he asked the girl to move her chair closer to his — their chairs were now touching — and he continued running his hand through her hair.

At first I assumed this was a public display of paternal affection, and indeed it may have been. However, he continued to run his fingers through her hair for 20 minutes in a sexually suggestive manner.

I decided I had four choices: 1) I could say nothing. (But what if it was later revealed that this man was a pedophile and this girl was his prey? I’m aware how some pedophiles operate from cases such as Elizabeth Smart and Sally Horner.) 2) I could confront the man or ask the girl if she was all right. 3) I could call the police. Or 4) I could alert mall security.

While I pondered whether to act or walk away, the man continued to fondle the girl’s hair. Something just didn’t seem right to me. I opted for No. 4. I pointed the couple out to mall security and told them what I had observed. I left the mall confident that security was keeping their eyes on him. Did I overreact? Name Withheld

My response: Not having been there, no one else knows what you saw. Normally my response would be “Your question is legal/medical/other professional service. Talking to a professional will answer your questions more effectively than a newspaper columnist.”

You sound like you did so, so I can’t say you overreacted.

The New York Times response:If what you saw was, as you feared, an adult grooming a child for sexual reasons — with the child perhaps having been manipulated into thinking that such attention was natural — notifying the authorities was obviously the right thing to do. But it’s most likely that something else was taking place. The behavior was going on in full view of passers-by; the man must have thought that what he was doing at least didn’t look wrong and no one else seems to have been troubled by the spectacle.

So perhaps this was indeed a display of paternal affection. Some psychologists worry that fathers tend to withdraw physically from their daughters as they approach adolescence, with harmful effects. Others think that boundaries must be set. I don’t have the relevant expertise to weigh in on this debate. But what you didn’t report is the girl pulling away or showing any signs of discomfort. Had you been inclined to investigate further, you could have greeted the two, in some amiably nonconfrontational way, and perhaps gained a clearer sense of what you’d witnessed. (Perhaps, for example, you’d learn that your sense of the participants’ ages was way off, and that the girl wasn’t a minor or his daughter.) Informing mall security may, in the event, have been better than calling the police, which might well have led to an unnecessarily traumatizing interaction. But because you didn’t stick around, you don’t know whether they ended up summoning the police anyway, perhaps in accordance with their protocols. Once you call in the authorities, you lose control over the outcome.

• ← Diversity: where are my invitations?
• 142: To Sam Harris, whom I hope to meet backstage Friday at the Beacon Theater (transcript) →