Jeff have you ever considered giving to specific people? It's quite ridiculous that college costs what you might give in a year, but $264,727 could concretely allow several people to attend college each year (state schools, community colleges, etc). Or how about removing bad debt, letting people rebuild their credit and start to save. I can think of myriad reasons why this is harder and less desirable (finding them, funding them, ensuring it has real impact, etc). But curious what your take on this would be.
If you click through to some of Jeff's other articles, you can see he's interested in effective altruism. Broadly, at the same total cost, paying for 5-6 globally wealthy people to attend college is going to have lower QALY impact than buying ~132,000 Long-Lasting Insecticidal bed nets ("LLINs") for people in regions with lots of malaria-carrying mosquitoes.
For more on effective altruism broadly, some resources:
If you strongly believe there are some unexplored avenues for impactful donations to individuals you should make the case to Givewell. It's what they're all about, and that seems to be what Jeff is mainly giving to (all those Against Malaria donations I assume were the top Givewell recommendation of their year). I think Jeff is doing the smart thing by outsourcing the analysis to Givewell who specialize in it.
"appeasing guilt with charity donations" implies something like "ads -> guilt -> donations". That the donations came years before the ads is pretty good evidence otherwise?
I make no judgement as to whether you are or are not attempting to offset guilt with donations, but no, I'm not sure the order of events matters that much.
A person who donates generously may more easily justify dubious money-earning efforts by saying, "it's really not for me so much, it's for the kids!" In other words, it is possible (again, not saying this is case for you) that one might take a job in advertising because they feel their donations provide ethical cover.
Bravo. It's weird sort of moral pretzel to advertise your donations which simultaneously wins you some respect and a whole lot of antipathy for being self-righteous. Unfortunately there's no way I know of to self-advertise your donations without being self-righteous but it's the right thing to do. Ironically you find yourself wondering do you pay more with your pocketbook for the charity or more with your social capital for the charity advertisement (which makes the charity more impactful).
By the way I don't donate anything to charity at the moment, although I plan to someday. So I'm speaking from a no-skin-in-the-game perspective.
