I give to charity — but never to people on the street. Is that wrong?

Editor’s note, October 18, 8 am ET: We’re bringing you some of our best-loved Your Mileage May Vary columns while Sigal Samuel is on parental leave.

The one below was originally published in September 2024.

This unconventional advice column offers you a unique framework for thinking through moral dilemmas.

It’s based on value pluralism: the idea that each of us has multiple values that are equally valid but that often conflict with each other.

Submit your own question here .

I think I have a duty to help people much poorer than me, and I give 10 percent of my salary to charities that I think are effective at preventing early death due to poverty.

I also live in a city with a lot of visible homelessness, and am often solicited for money.

My brain says that this is not an effective way to help people; the people asking might not be the neediest among the homeless in my city, and the people I’m sending malaria bednets and pills to are even needier.

At the same time, I feel callous simply ignoring all these requests.

What should I do? Dear Would-Be Optimizer, Nine times out of ten, when someone’s got an ethical dilemma, I think it’s because a couple of their core values are conflicting with each other .

But you’re that tenth case.

I say that because I don’t actually believe your question represents a battle royale between two different values.

I think there’s one core value here — helping people — and one strategy that’s masquerading as a value.

That strategy is optimization.