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Non-philosopher here. I'm thinking that I have problems with the "freedom is the main thing" point for two situations - morality centered around command deontology and might-makes-right positions.

I'm a deontologist (sort of; nobody is really a deontologist all over) - I think what that right is right broadly because I was told to do it. It happens that my deontology-rules overlap with your everyone-gets-equal-freedoms thing, but the foundational aspect is subtly different; it's not based on freedom, but recognized authority.

So imagine a religion exists that has the following three tenets:

1. A god rules the universe who determines what is right and wrong; he can actually do this, and things he determines to be right/wrong actually are right and wrong on an abstract/metaphysical level.

2. The god has a right to do this, i.e. is sovereign.

3. Said god has determined that people with shoe sizes under 7 are a slave class.

If the person is convinced on 1-2, and that 3. was actually coming from the god, he'd believe A. In a system where obligation, not freedom, is the driving force and B. Where freedoms of others are restricted for a reason besides "I say so" that actually references the nature of things and the universe (whether or not you think it's in error).

An example of this that's a little more relevant is the general expectation in Christianity that children obey and honor their parents. This restricts their freedom substantially in a way their parents might very well not be restricted and isn't based on "I said so" - it's based on a reference to obligation to an outside authority, who has set up the universe in a certain way.

Might-is-right person might very well believe that every person should do what they want to the extent they can do it - when you try to restrict them with "because I said so", they will say "well, no" and punch you in the nose. This isn't a very good moral system, but it's at least complete; there is nothing in them resisting your commands and your logic/reason that contradicts "I should do whatever I want that others can't stop, and so should everyone else".

I might be thinking about both of these wrong - I'd be interested in hearing how.

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Your thinking mirrors mine in a lot of respects - so much of the critiques that follow are critiques of my own thinking.

1) The self that deliberates and acts upon the reasons it finds in deliberation might be bigger or smaller than an individual human. Firms and governments might assess their goals, and me-on-some-lazy-morning will deliberate on how much he wants to cooperate with me-in-general. So the “I” of the skeptic could mean many different things, or might have very ambiguous boundaries.

2) This is a very classic Kantian point, so you are probably already familiar with this. But if the relevant kind of freedom we’re starting with is “the ability to choose your actions based on reasons you find compelling,” then I’m not sure that the skeptic is really deliberating about whether to surrender her freedom; rather, she is exercising it. This isn’t to say that the “cost of morality” is nothing but rather than its cost is whatever the skeptic would otherwise want but that moral considerations would force her to abandon (the tastiness and nutrition of meat, or money that could be enjoyed personally rather than surrendered to charity or easily-avoided taxes, or whatever.) And ironically by this same token I don’t know that we can conclude that the skeptic is transcendentally forced to admit the value of freedom by their reluctance to sell it away except at a worthy price; rather, freedom is (per the existentialists, as you note) just something you’re stuck with until you off yourself or accept a mind control device or the like. (That most people don’t want those things at least in part because it would mean an end to their ability to make choices based in reason *does* mean that they empirically value it, but I don’t know that this is true of the skeptic in general.) Note that even a soldier pointing a gun at your head saying “praise the emperor!” takes away this kind of “primordial freedom” (until the trigger is actually pulled); you can either decide that you prefer your life over your dignity and exercise your primordial freedom to do that, or the opposite.

3) By the same token, the claims of “reason” that the skeptic must concede are quite limited - she needn’t think that everyone has access to reason, or that statements can be readily generalized outside of a very thick original context, or that we can be skeptical of any claim and demand reasons for it (even if that’s what she’s doing wrt this particular claim) or many other things. She just needs to be amenable to the idea that there are some considerations that would give her compelling reasons to do things.

Now at the end of the day I think Enlightenment slogans like “equality, liberty, reason” are good ones that I want to implement as far as possible. But I don’t know how robust versions of these we can smuggle in through this kind of transcendental argument.

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