Why don't anarchism or libertarianism work?
What keeps us from adopting personal freedom as the central principle of society, and rolling that out across the world?
There are 2 main reasons. One is simply "freedom" is often poorly defined, and there are many cases where freedom for one person involves the oppression of another person.
But the larger reason is pragmatism. When ideas like anarchism and libertarianism are tried, they just don't work. I spent many years in or adjacent to many attempts at "intentional communities" and even there, where you have 100 or 200 people who come together in the hope of establishing a small society that can live by rules of freedom, mutual respect and direct democracy, things just don't work, so what hope is there of building anything larger?
I do think that anyone who is interested in anarchism or libertarianism should spend some time as part of a community like this. It's a powerful education, to realize how much people disagree, even when they all start off with the same politics and the same nominal goals. Please read this, as it gets to the heart of the matter:
The other thing you run into, in communities like this, is how much "freedom" for one person is oppression for another. This comes up constantly around sexual matters.
Consider one of the most famous and oldest intentional communities in the world: Twin Oaks, in Virginia. Many books have been written about the place. And yet, what was the place like for children, especially girls? Go talk to the folk singer Devon Sproule. She grew up there. She has suggested that she had a rough time because of the lack of boundaries and limits around sexual matters.
A question that often comes up is what, exactly, is an appropriate age of consent for sexual matters? Most of these communities live somewhat outside the law, and set their own rules about these things. And you'll find plenty of men in their 20s who suggest that sex with a 13 year old should be legal, so long as the relationship is consensual. But that comes back around to the question of whether someone at 13 can meaningfully give consent. And if not at 13, then maybe at 14 or 15 or 16? When, exactly? How should the community decide? If the community creates a rule, does that mean it is imposing on the freedom of those who wish to engage in a relationship?
I've heard these conversations a hundred times, and neither side ever wins over the other side, which is one reason why 90% of these communities eventually fail.
The important thing to note is that these conflicts come up in fairly small groups, where everyone is politically aligned and where everyone is committed to personal freedom. And yet, people quickly decide their needs to be some limits, and then who sets those limits, and how are they enforced? If someone breaks the law, how should they be punished? Is it ever acceptable to call the police? Many of these communities have a rule that you cannot call the police ever, that all matters should be resolved by the community itself. But that means the heavy hand of punishment needs to be worked out by the community, and this often goes against the original understanding that the community would be a unique outpost of unlimited personal freedom.
So almost the whole centuries-long debate about freedom and the rule of law ends up being revisited, even in small communities that were trying to maximize personal freedom.
So what is the hope of building larger structures? What hope is there for nation wide structures? Large structures grow up organically from smaller structures, and if you can't get something to work for a 200 people then you will never get it to work for 200 million people.