There is a two-sided dillema that pops up in conflicts over issues of freedom and domination. One side of the dillema is the problem of "involuntary liberation", while the other side of the dillema is the problem of "voluntary authoritarianism". Both of these seem like bald-faced contradictions that throw a monkey wrench into any attempt to coherantly define freedom, but they actually pop up quite frequently in conflicts between various libertarians and anarchists. The begged questions that may clarify how such contradictions arise is "voluntary in what sense?" and "liberation in what sense?".
What do I mean by "voluntary authoritarianism"? I mean a situation that is predicated on something that is voluntary in some sense or aspect, and yet is ultimately authoritarian in nature. For example, let's assume that "homesteading", "exchange", and "inheritance" or "gift" are voluntary modes of aquiring property over a given geographical area. That is, it is "voluntary" in the way that it is obtained. But as a question aside from one of how territory is obtained, those that own the geographical area exersize essentially unlimited power over those that happen to occupy the area that they have voluntarily obtained. Hence, in spite of the fact that the area was aquired "voluntarily", there is an authoritarian relationship at play in which the individual or group that "voluntarily" obtained the territory theoretically make whatever rules they want while the non-owners must obey their rules.
Let's be clear about this: the scenario just described would be a state in the Weberian definition of the term (or at least involve a state-like entity), in spite of the "voluntary" nature of territorial aquisition. It constitutes a defacto "territorial monopoly of ultimate decision-making" relative to the geographical area in question. And yet it initially came about through "voluntary" means, in terms of the way in which the geographical area was obtained. This illustrates an important point: that the qualification or criteria that a given geographical area is aquired through "voluntary" means is insufficient as a condition for freedom. The excersize of "ultimate decision-making power" over a given geographical area does not suddenly cease to threaten people's freedom simply because the area was "homesteaded" or "exchanged for".
There is also a factor of time in situations of "voluntary authoritarianism". While the prior example shows how it possible in some sense for a "state" to arise out of an initially "voluntary" mode of property aquisition, the annoying issue of "voluntary" slavery is similar, except in the latter case it has more to do with contracts than direct modes of property aquisition. It is theoretically possible for someone to sign a contract stating that they will work for and obey the orders of another individual or group, for the rest of their lives even. In terms of the simple act of signing the contract without initially being threatened with aggression, such an act would indeed be "voluntary". But as soon as the person tries to opt out of the relationship and another party proactively threatens violence to make them continue following orders into the future, what started out as a "voluntary contract" has taken on the character of any old authoritarian relationship. The contract itself is irrelevant to what explicitly is "voluntary".
The knee-jerk response at this point is for the defender of "voluntary slavery" to object that "you can't force them to be free", since that would appear to be a contradiction in terms. This is misleading because the person in the scenario actually doesn't want to obey orders anymore or continue to be a part of the relationship. The entire point is that the relationship has explicitly ceased to be "voluntary", and to perpetually enforce the contract would be pure subjection at this point. If I defend a slave that is trying to flee their master, I'm not forcing anyone to be free. It's their master that is trying to force them into not being free. If the "voluntary slavery" notion is taken to its logical conclusion, one would have to defend any sort of authoritarian relationship as long as it is traceable back to a legally binding contract.
It seems like the fundamental error of such "voluntary authoritarianism" is that property and/or contract are treated as ends in themselves that override freedom, or freedom is defined as a derivative of them. As a consequence of this, everything that one would otherwise object to in the abscence of contracts and the proper modes of property aquisition is relegitimized in the framework of property and/or contract. Hence, slavery and the state remain in substance, and differ only in the form that they take in terms of how they initially come about, which may initially be voluntary in nature. This may seem counter-intuitive, but something can start out voluntarily (or at least with its foundational qualities not involving aggression) and become involuntary or authoritarian over time. It also leads to a conclusion that may offend the average market-libertarian ear: if we want to meaningfully favor freedom, we must realize that freedom inherently limits property and contracts.
With all of this being said, there is another side of the coin here. While there are specific problems with viewpoints that end up effectively leading to the contradiction of making people "free to be subjects", there are also certain viewpoints that end up leading to a genuine contradiction of "forcing people to be free". The most explicit example of this in large-scale politics is probably the neoconservative line on foreign policy, in which proactive aggression and nation-buiding is endorsed in the name of freeing people from the control of foreign governments and "keeping the world safe for democracy". The idea is that one is doing a benevolent service to the people living in those areas by stepping in fighting the organizations that more locally control them. There is often a humanitarian veneer to it that gives it a veil of legitimacy.
Upon reflection, it may initially seem like there is an element of sensibility to this if one thinks of it in terms of helping slaves flee their masters. But that isn't really how such policies really work. For one thing, who exactly belongs to "the enemy" to be fought is often unclear, and the general population ends up being either caught in the crossfire or feeling invaded, which leads them to defend themselves. And so, to some extent, one ends up in a conflict with the very people that one is claiming to be liberating. The very nature of large-scale warfare ends up doing damage that is well beyond the limits of explicitly governmental targets. Furthermore, even to the extent that what could be considered oppressors are being fought off, it is under the pretext of imposing a new group of oppressors.
It reaches a point at which one is actually subjugating and killing people in the name of liberating them. The "liberating force" makes a power grab of their own, either directly (in the form of running the government) or indirectly (in the form of establishing a new puppet/satellite regime). Even the mere motive of freeing people comes into question, and it ends up looking like the motive of the "liberating force" is to become masters themselves or impose a new set of authorities onto the people that are supposed to be "liberated". It's analagous to slavemaster A taking out slavemaster B only as a pretext to replacing them and gaining control over the other slavemaster's subjects. The claim to be freeing people, whether it is genuinely intended or not, is illusory in substance.
A similar issue is involved with opposition to standard wage labor. Suppose, for the sake of argument, that an anarcho-communist society was achieved. Noone works for wages under an employer. But let's suppose that, for one reason or another, a particular individual decided that they wanted to work for someone else and another individual was willing to be their employer. One can protest until one is blue in the face that noone would have any reason to do that in a communist society, since there is supposed to be post-scarcity conditions, but let's assume that some people do anyways. What can the anarcho-communist really do about it? Are they really going to try to universally ban all employment contracts, and how would they possibly do this without some degree of aggression at some point down the line?
I think that this scenario bumps into a genuine "force them to be free" dillema. It seems akward and counter-intuitive to try to proactively intervene to stop someone from initially entering into an employment contract, while that person protests the whole way and genuinely wants to enter into it. It seems like the anarcho-communist more or less has no choice but to tolerate it to some extent. To claim to be "liberating" someone while they emphatically don't want you to and while they persistently object doesn't make any sense. While the "voluntary slavery" proponent doesn't take freedom of exit into proper account, anyone that favors explicit "involuntary liberation" in this way seems to not take freedom of entry into proper account. If "freedom of association" is to mean anything at all, both entry and exit must be considered.
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