The Psychology and Morality of Optimal Philanthropy

This [designing careers around being able to donate as much as possible] one I see as highly damaging. Human psychology is such that, in order for a movement to get long-term, voluntary participation by highly capable people, stuff needs to be fun.

I agree with you here -- not everyone can be a professional banker philanthropist. But I think the idea deserves attention. Perhaps a better idea with regard to donating more and not regretting it psychologically is learning how to be more frugal and increasing one's budget for donations.

A lot of the people I know who donate in the 10-50% range to effective causes actually love it a lot. And indeed, the research needed to figure out where to donate is often novel, challenging, and gets better over time -- some of the elements of Fun.

I also agree with you about being sure where the most-earning careers are. And in not ignoring the intangibles of certain careers, like authority that can be used to leverage public opinion. I think Peter Singer, as a professor, has done a lot more for optimal philanthropy than any investment banker, for example.

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If not donating surplus money is morally equivalent to causing whatever bad outcome the donation would prevent, you are now twice as guilty, since the amount you aren't donating (20% vs. 10%) is twice as large. This is despite the fact that the total amount of good done is also twice as large. Why punish an improvement?

Punishing an improvement is obviously not the utilitarian thing to do. This is why Peter Singer never actually condemns non-donators as moral monsters, and actually has a standard for giving equal to about 5% your income. Giving What We Can is only 10%. These are easily reachable.

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Another huge problem is the creation of unbounded obligations [..] With this line of argument, there's literally no point at which one can sit back and say, "I've fulfilled my duty to charity - there's nothing more to do".

You're right, and that's because there's always more that you can do. I think it becomes much less confusing if you don't think of doing everything as morally good and anything less as a moral evil. Think of things as morally better or morally worse, and remember that's from a utilitarian perspective.

And also keep in mind that no-one can be an ideal utilitarian. It's like striving to be an ideal rationalist. You can only get better, the point of perfection is impossible. But that doesn't mean that utilitarianism or rationalism is flawed.