While reading these lines, what actually crept into my mind were ethical considerations. I've written to you about his before, but I'll try to make into another take that while biting itself, like the worm Ouroboros, does not repeat.
After reading and pondering your blog and other materials in the last few months, I have become more favorably disposed towards utilitarianism, but I am still strongly convinced that, for all of its good points, there are some blind and dangerous alleys it leads to when followed too intensely and too exclusively.
Myself, I have a strong liking for deontology, but I think I am aware of its limitations. If we are to abide by natural, immutable, unbreakable laws, it is fair to ask where these laws come from. Being of a sceptic persuasion, I cannot attribute them to some God-like being, so they would need to be derived from axioms of reason, of what creatures endowed with such a property would agree upon. Kant tries to do this, and he doesn't do an altogether unsuccessful effort with his Categorical Imperative: I find really engaging both his reformulation of the golden mean, his prohibition on lies and the way he sanctions humans as non-instrumental ends in themselves. Still, it is a proposal that includes many impracticalities in practical implementation, and utilitarianism is one of many examples that one can build systems that sound as plausibly rational in their choice of moral axioms as anything that old Emmanuel can dream of in his philosophy.
There is another level, though, at which I find my inclination to deontology useful: even if you do not believe that some set of norms sanctioned by tradition and the community are to be regarded as sacred an unbreakable, the thing is they are very good guardrails for individuals given the enormous degree of uncertainty that we are forced to live in. Such an uncertainty is easy to minimize or ignore when one is (of feels that he is) really smart and knowledgeable, and that said rules have outlived their usefulness and purpose. As your blog shows, you are not unacquainted with Chesterton's fence. And besides, rule-based utilitarians also resort to some version of this when escaping from the aporias of act utilitarianism.
This guardrail is all the more necessary for two reasons: the first is that maximization is perilous - this is an argument that has been made much of by arguably the most important EA thinkers themselves, both McAskill and Ord. And maximizing is precisely what you were doing, and arguably, have been doing all your life, usually at the expense of your own happiness and well-being. I would add something, perhaps, here: I believe it is not wholesome to be a self-renouncing saint. Yes, meaning, sense and a call can be found in this, but it goes so against the basics of human nature, and also violates a (deontological, and probably virtue-ethicist) imperative for valuing your self not as a tool or instrument of some grand and superior force or principle, but as a person endowed with a need for flourishing and the pursuit of happiness. I would go further than that, and state that this is not just a need, but an obligation, for which the subject must follow up with a demarcation of a personal space that can never be violated by all and any demands placed upon it by society, others and/or any beliefs that oneself might hold. I can see how this could be construed as a certain rationalization of (a degree) of egoism, but that still doesn't make it less true for me.
The second reason why the guardrails of deontology (and virtue ethics) are necessary are because we are a very good rationalizing animal, and all the more so the more intelligent we are. With this I go back to the quoted passage from above: we can delude ourselves, if clever enough, with arguments that justify certain actions as predicated on the reason and axioms we follow; and we can be deluded as well by those even better at reasoning and wordsmithing than ourselves. You yourself are a very sad exemplification of this: it would otherwise beggar belief how an absurdly intelligent, galaxy-brained woman like yourself, and one trained from so young in rationalism and scepticism could have failed so spectacularly here, even when taking into account extraneous considerations to the power of Sam's rationalizations (his prestige within your community, his success, your infatuation with him, your insecurities, and your belief that being close to Sam was high expected value and a fair chance of 'being in the room when it happens' and of possibly maximizing your own participation in World Optimization).
I am no moral philosopher, and definitely no saint, but I'd dare say that even with a 100% belief in utilitarianism, moral uncertainty would probably dictate that in practice, one should be at most, 60% utilitarian, and divide the other 40% in whatever proportions between deontology and virtue ethics. And probably, the allocation should not be random, but rather, the stronger a utilitarian postulate seems to violate any of the other two, the stronger one should probably not follow along with it. Call it a triangle of ethical inequality, if you will.
But I fear this post is too long, and that I might have jumped my own guardrails of support, brevity and consistency. I would add one last thing, though: the good work you currently are doing -the food pantries, the tutoring, the soup kitchens, the tax help work- might seem, from your perspective of yore, the 'purchase of fuzzies', in rationalist speak. It is not so. Not only does it do good to you (which is necessary for your healing and flourishing, for your connection with real people, and not just abstract ideas), it helps real people, even if less than you would have hoped in previous dreams of the widest possible circle of effective helping. Such a circle has perforce had its circumference dramatically reduced for you, but I trust you'll be able to expand it in the future.
-And how do you apply that education to what you do?
-It has made me distrustful of language.