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

The quest to give effectively feels like it’s turning me into an cold-hearted jerk.

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. I can tell from your phrasing that you’re really into it. You don’t just want to help people — you want to help people as effectively as possible. Since extreme poverty is concentrated in developing countries, and since your dollar goes much further there than it would in your home country, your optimizing impulse is telling you to send your charity money abroad.

Obsessing about being a good person can backfire. There’s a better way.

Optimization started as a technique for solving certain math problems, but our society has elevated it to the status of a value — arguably one of the dominant values in the Western world. It’s been on the rise since the 1700s, when utilitarian thinkers seeded the idea that both economics and ethics should focus on maximizing utility (meaning, happiness or satisfaction): Just calculate how much utility each action would produce, and choose the one that produces the most.

You can see this logic everywhere in modern life — from work culture, with its emphasis on productivity hacks and agile workflows, to wellness culture, with its emphasis on achieving perfect health and optimal sleep. The mandate to “Live your best life!” is turbocharged by Silicon Valley, which urges us to quantify every aspect of ourselves with Fitbits, Apple Watches, and Oura Rings, because the more data you have on your body’s mechanical functions, the........

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