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I could live and marginally improve other people's lives in a country with an authoritarian, oppressive regime. While doing so, I will pay taxes and will generally increase the chances that this regime will last for longer (this might not be certain, but for this particular question, let's assume that this is highly likely). Alternatively, I can disengage by moving to another country, but there I should "start from scratch" and will do even less towards achieving my moral goals for the rest of my career than if I stayed (this might also not be certain, but let's assume again that this is highly likely).

How should I think about this ethical dilemma? Or should I use an entirely different questions/perspective/paradigm in thinking about this? Is this a dilemma at all? What are the standard googleable terms for this in moral philosophy?

Coming up with an utilitarian calculation regarding the expected value of total "good" vs. total "bad" that I will do by staying vs. leaving I think is practically impossible and would be self-deceiving because of the immense complexity and fundamental future uncertainty in the areas of economic/social/political/career choices.

Googling only leads me to the Wikipedia page on necessary evil but this doesn't look relevant to me. I also think there might be a relation to the Prisoner's dilemma (as in, contributing to an oppressive regime might be an act of entering a bad Nash equilibrium), but I'm not sure what are the moral implications of this.

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    For a general framework to think about this see SEP, Moral Dilemmas. Moral values are often hierarchical, and some take precedence over others. Utilitarian calculation is a utopia, but weighing costs and benefits as fully as possible in some form is an important part of deliberation. One can view the costs of whichever decision as a moral 'debt' to be 'repaid' by subsequent actions. In this particular case, the contribution-by-taxes is rather minute and they serve other, legitimate, purposes too, so it is hardly a consideration.
    – Conifold
    Oct 10 at 21:53
  • a) You are not your words, you are your actions; b) The synthesis of all of your actions is expressed only in two acts: attraction or rejection; ergo) In consequence, you can say whatever you want, but if you stay in a country, you are stating that for your utilitarian account, where you live is better than elsewhere; note) in your utilitarian account, moving seems expensive and risky. Believe me, it is not. I've lived in five countries, and every time it worth the risk and effort. There's no perfect country, all have issues, but changing is worth the risk.
    – RodolfoAP
    Oct 11 at 17:32
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You might like this answer relating game theory & the social contract: Is the tyrannicide perpetrated by William Tell morally legitimate?

Indirectly relevant might be this discussion of wisdom as our dilemma-solving faculty, which depends on a practice of discovering the integrated centre of our concerns: Wisdom and John Vervaeke's awakening from the meaning crises?

There are many reasons to continue aid work in countries with despotic leaders & corruption. Charities are scrutinised on this, & have clear policies to prevent issues & manage conflicts of interest. Effective Altruism is a framework advocated by philosopher Peter Singer, but it doesn't as far as I know have specific answers on these issues, & is widely criticised in practice. Many people who oppose fossil fuels, the arms trade etc, don't check where their pensions are invested, & that's how those industries are financed, systematically thinking about choices like that is at least as important.

The paradigmatic case for decision making on difficult choices about staying & cooperating or leaving & opposing, is Nazi collaboration. If you look at war crimes trials, they distinguish between what people were ordered to do, & chose or volunteered to do, & this applies when working with a bad regime - the real danger I think is choosing to do or avoid things because it would cause 'trouble', or might create some problem you can't be sure about, & consequences aren't clear-cut. It comes down to integrity, & conscience.

Sartre dealt explicitly with some of the issues, in The Republic Of Silence, short book Existentialism Is A Humanism, & play No Exit. Well worth reading. He has been criticised by later writers, but not by other resistance fighters & compatriots who lived through those times.

Philosophy around non-violence & non-cooperation is interesting, like the research on a century of protests that Extinction Rebellion base their strategy on, mentioned here. A solid case can be made that to be really effective, there has to be a fear on the part of government about escalation - exactly why, I suggest is highly local & specific involving given circumstances, & certainly isn't limited to realistic threat of violence. But learning about past struggles in depth is one of the most useful things to do. Indian Independence, ending South African Apartheid, US Civil Rights. And now Hong Kong & many other places. It's not a binary of collaborate or leave.

I'd suggest you've already made it pretty clear you lean towards staying, leaving & starting from scratch is a bit of a 'nuclear option'. All the more reason though to clarify for yourself what events would push you to that, & to know how you would - repercussions for truly doing the best good you can, could force you to leave, & feeling you can't or aren't ready might stop you doing good. You have implicit knowledge of the place you are & networks there, surely it is exactly where things are difficult that the most good can be done - finding the places injustice can be pushed against.

I feel this is more, an issue for reading people's real stories, & for absorbing literature, than for philosophy. The complex balance of when & how to do good, what risks to take knowing who they might impact, come down to deeply personal choices, that express an individual, moment by moment. I found 'The Unbearable Lightness Of Being' a really powerful meditation on compromise, choices & expression of identity.

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I would say you don't need any new moral philosophy besides your own. What you need instead is a decision theory framework for analyzing what actions to take based on your moral principles.

In particular, suppose you have a way to estimate the net moral value of each action (as opposed to not taking that action). There would be some uncertainty, but suppose you know the set of possible outcomes and for each of them you have an estimate of its likelihood and its net moral value. Then what you need to know is how to decide whether or not to take that action.

Common approaches include expected value theory or expected utility theory, but both have severe flaws even in secular contexts. I think that for moral decisions you must be even more careful. For example, consider an action causes one person to die fast but results in a hundred others having a longer life. Would it be a good action? What if that one person is a (intentional) murderer? What if the hundred people are all murderers? At least you must be able to consistently evaluate choices given sufficient information.

After you decide on your own moral framework for such evaluation, then in the absence of sufficient information you must be careful to evaluate decisions based on your risk profile. For example, if an action has 5% likelihood of causing an innocent person to die faster against his/her will (e.g. death penalty for a murder with not completely clear evidence) but 95% likelihood of preventing at least one innocent person to be murdered next, can you accept that level of risk?

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