Money Talks: How to Make Those Hard Conversations Easier

Tips for preserving your boundaries and other people’s dignity.

“Money complicates relationships. There’s no exception to that.”

Photo by Science Photo Library/Getty Images

When Devon showed up at my door asking for money, I wanted to help him. I couldn’t bring myself to close my heart to someone in need who was standing right in front of me. So I went for my wallet, and gave him money.

What followed should have been predictable: He came back—repeatedly, over the next few months, asking for food, cash, rides, and help with a hotel room. He even invoked the health and happiness of his 3-year old daughter and 50-year old mother.

I suppose experiences like this sometimes lead us to avoid helping others who have less than we do, out of fear that their needs will be never-ending, and they’ll become a burden on us. For many people, it is reason enough to stand back and refuse to get involved. But is there a way to help without becoming overwhelmed or feeling like someone is taking advantage of you?

I really wanted to know, so I began to search for a set of guidelines for how to best help someone in need, rules that maintain dignity on both sides and can establish a healthy relationship. After all, clear boundaries are essential to any partnership. And nobody wants to feel like a sucker.

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Unsurprisingly, such instructions aren’t easily found. If they were, responding to requests for help—from homeless people on the sidewalk, acquaintances in need, or even friends—wouldn’t be so fraught with difficulty and discomfort. Let’s face it: It’s hard to figure out what to do when someone asks for money. Especially when it’s obvious you have more than they do.

But while there are no easy answers, there are ideas about how that kind of interaction can go more smoothly. In the case of Devon, who was homeless, a lot of people would claim that I should’ve contributed money not to him but to an institution that works with very low-income people.

One such person is Tessa Madden Storms, who works for PATH, one of California’s largest homeless service providers.

Storms says, if you want to give money, get invested in organizations doing that work. “They’ll invest it in services that help those people, moving them off the streets, ending homelessness.”

Donating to an organization also sidesteps the insidious fear that someone on the street might use the funds for drugs or alcohol.

But there are pretty strong arguments for the other side as well. Pope Francis has thought carefully about how to respond to the poor. In an interview with an Italian magazine last year, he recommended giving money to those who ask and not worrying that they might use it to get drunk.

If “a glass of wine is the only happiness [someone asking for help] has in life, that’s OK,” Pope Francis said. Giving money to someone in need “is always right.”

His position is borne out by research. The U.S. organization Give Directly transfers cash donations directly to needy individuals in East Africa, and its prodigious follow-up research has shown that people consistently use the money well—to alleviate hunger, access housing and education, start businesses. Small donations usually won’t change a life here in the United States, but they can help people meet very real basic needs, like food and shelter for the day.

Once you give something, let go of it and your expectations of how it will be used.

But once you give something, let go of it and your expectations of how it will be used. “Once it’s out of your hands, it doesn’t belong to you anymore,” says Sarah Erdo, volunteer and community engagement manager at the Philadelphia-based Bethesda Project. “I don’t believe in the notion of being taken advantage of, if you’re giving freely.” There’s freedom in that, in trusting that we know what’s best for ourselves.

But let’s say the request is for a larger amount—maybe your nanny, who happens to be an immigrant, who’s asking you for help. How do you respond?

Be honest, says Josiah Haken, vice president of outreach operations at New York City Relief. “You can say, ‘You’re putting me in an awkward position,’” he explains. It’s also totally appropriate to ask why the money is needed, he says. After all, the asker has opened the door to that conversation.

Maybe, Haken muses, the reason is that you’re not paying your nanny enough. Or maybe she needs money for something that has real leverage potential: a child’s school fees, or a certification that would allow the asker to get a better job. That’s rarely a bad investment. The same is true in the case of a genuine, unavoidable crisis—but it’s fair to clarify that your assistance is a one-time thing.

More often, though, the request falls into a gray area. In those cases, it can be better to investigate how the other people can help themselves. That might mean devoting time to researching the issue and helping them find a solution. It’s a gift that’s empowering, not patronizing.

But remember this, says Ali Jost, a clinical social worker in Washington, D.C., who works in community health: “Money complicates relationships. There’s no exception to that.” That doesn’t mean you shouldn’t give. In a relationship that’s not particularly important to you, you might decide it’s worth it.

Perhaps the best response, in the end, is to start fighting to change the system.

But that might not be tolerable with someone you’re close to. “You could make a choice to say, ‘I’m not going to give you money because I care too much and don’t want to make the relationship weird,’” Jost says.

And that’s OK. In fact, it’s always all right to say no to a request for money. It doesn’t make you a Grinch or a bad person. But what just about every professional do-gooder emphasizes is that it’s crucial to still treat the asker as a human, someone of value—particularly if they’re homeless. Don’t judge. Look them in the eye. Ask their name. Have a conversation.

“What comes to mind is a beautiful quote from Mother Teresa: ‘It’s not how much we give but how much love we put into giving,’” says Shane Claiborne, an activist who leads an intentional community in Philadelphia that works closely with low-income people. It’s about recognizing someone, he explains. “I think that anytime we give of ourselves, and especially of our time and energy, that’s a precious thing.”

One way to make the uncertainty of being asked for money easier in the future is to prepare yourself. Get to know the social services landscape in your city so that you can point people to available resources. Determine how much you’re comfortable giving next time—or decide that you don’t want to give money at all, and stock up on socks or granola bars to hand out instead.

In the case of Devon, for example, I later heard about a well-respected local nonprofit that helps get homeless families into housing. I wish I’d known about it earlier, so that I could’ve sent Devon there that first night he came by. I’m positive I still would have given him money then, but I wouldn’t have felt a pressure to continue.

There’s no single right answer. Many of us struggle with this because we know, consciously or subconsciously, that our society is profoundly off-balance—that the distance between the haves and the have-nots has mushroomed to absurd proportions. Unfortunately, those complex dynamics won’t be addressed with a donation or two. Perhaps the best response, in the end, is to start fighting to change the system.