You can't optimize your way to being a good person

Yeah, that's fair.

In my previous apartment, there was a guy named Julius. I really liked him, he was very pleasant to talk to, funny, charming, and just very nice.

We were in that apartment for three years, and nothing too remarkable happened, but the last year, Julius fell into some kind of lifestyle that I'm unsure of the details of, but ended up with him constantly stoned, missing teeth, and evicted from the apartment.

He was still in my neighborhood (homeless as far as I could tell), and he would still talk to me, always really polite, but with increasingly-yellow eyes, and it made me really sad, because I wouldn't wish that fate on anyone, let alone someone who was always kind to me.

My wife and I discussed maybe giving him some money to try to get back on his feet, but we decided against it because we were confident that if we did it would likely go to drugs. We really wanted to help, but we were afraid, like you said, it would be a short-term want overshadowing a long term gain.

If I had genuinely thought that writing him a check for $1,000 would dramatically improve his life, I would have done it in a heartbeat, but I didn't, and I felt like there was a good chance it would fuel a bender that would lead to an overdose.

I would occasionally buy him lunch at the nearby Wendy's, and I offered to try and help him fix up his resume to maybe make him more employable, but nothing ever came of that.

We eventually moved from that apartment and I'm not sure what happened to Julius. I hope he's ok, but I suspect that he's probably dead now, from an overdose or alcohol poisoning. A part of me wishes I had given him some money to dig himself out, but I think I made the right choice.

I don't lose sleep over my actions on that one; there wasn't really anything I could have done much different. Sometimes sad shit just happens, and it's no one's fault.

While the author doesn't explicate it, the author is operating within a particular moral framework that has certain conclusions on what actions are moral in certain situations, and in this framework, moral actions can bring the agent suffering. The article focuses on one category of moral action. The author observes that it is possible for a person who continually internally contemplates and "tries" to externally act according to that moral calculus to do so in a way that brings them to a psychological suffering. (My description is more general; the author uses 'optimization' to describe their) Hereafter, we shall to 'continual internal contemplation and "trying" to externally act according to that moral calculus to do so in a way that brings one psychological suffering.' by Practice.

They want to argue that this Practice is not itself morally good (the first paragraph) I find the author's argument incomplete. They seem to implicitly make the additional reasoning steps: because the Practicioner may themself suffer greatly, this Practice is not moral. This step needs support. After all, if I fracture a leg to save a healthy baby from a car accident, that's probably a moral act even though it brings me suffering.

I shall provide an argument for this step that works in most cases (and in exactly the cases that I think it should work for). Observe that most parents recognize that it is probably good to stay healthy, because a healthy parent has the capacity to contribute more to their children's happiness. But a parent would still fracture a leg to save their child from a car accident. Here, the moral calculus is more visible because we are substituted in the more visible physical health rather than psychological safety, and the more proximate children for the remote person. Similarly, a Practicioner should desist to the extent that they can sustain their psychological health that they have the capacity to contribute more to good. And there are cases where that psychological health ought to be sacrificed, because the external situation is sufficiently critical.

I will also talk about the psychology in the analogy that I have given. There are frequently times where parents don't see that their health is important to the well-being of their children, and allow themselves to abuse their health for unimportant reasons/causes. Analogically, a Practicioner like the author and their peers pursuing 'optimization' likely allowed their psychological well-being to suffer for unimportant reasons/causes.

Another point: a parent who has made a visible sacrifice for their child(ren) often feels good about it. But this psychological response to a sacrifice is conditional on the situation being simple enough to be "emotionally recognizable". As an analogy, suppose that through a charity you have donated money to fund a life-saving operation of a distant child, and despite paper and institutional guarantees, you do not so much even see a photo of the person whose life you have saved. That emotionally hits very different as spending the same amount for a relative that you meet often, and also for one's own child; after all, direct sense-perception provides very good evidence. As a methodological point, I think it helps to explore cognitively building the infrastructure so that you feel the psychologically appropriate reward to sacrifices for sufficiently certain good, but remote, causes.

Finally, note that there are moral frameworks for which this argument is completely irrelevant. For example, Aristippus argues that one should practice instant gratification, in which case such deliberation on methods seems irrelevant.