Most people who put a lot of emphasis on the alleged conflict between freedom and democracy seem to assume a laughably simplistic definition of democracy taken straight out of early-to-mid-20th-century political philosophy. Basically, when they say "democracy", they mean "majority rule". And of course, if getting 51% of the vote were all there was to democracy, I would wholeheartedly agree that it's a nasty thing.
But political philosophy is one of the fastest moving sub-disciplines of philosophy, and most people who take philosophy and/or political theory courses in the first 2 years of college (or read introductory books by themselves) are unfortunately not given a real taste of the latest developments in democratic theory. This makes them pick up an outdated, straw-man notion of democracy (anybody read Robert Dahl?) and argue passionately against it. But if that's what they're doing, they aren't really adding anything to what Schumpeter said 60 years ago. What a waste of precious brain cycles.
Most influential political philosophers of the English-speaking world in the last half century (Rawls, Dworkin, Gutmann, Thompson, Bohman, Dryzek, Young, Mansbridge, etc. -- and of course Habermas) refuse to equate democracy with "obey whomever 51% of the population votes for". To them, democracy is all about giving the voice of reason a chance to be heard, even if it means departing from political systems that currently pass for democracies. They usually call for much more powerful constitutional constraints on democracy so that the most important human rights become extremely difficult to override even if you have a supermajority. Like all tools, democracy needs to be limited in its scope. If you have a hammer... you know how it goes.
I agree that there are many interesting developments in political philosophy on the nature of democracy. The issue is that such academic debates have almost no impact on any current political system that describes itself as a "democracy" and the poor citizens that live under it.
One of the best ideas I got from reading Marx (which also shows that people who read Moldbug tend to read widely, hey) is that political ideals aren't real. They don't matter. All that matters is the living breathing primates that inhabit our political systems, the stuff those primates have, and whether the primates are happy. Bad political systems are bad because they cause cruelty to animals.
"Freedom" is simply a matter of the monkeys being able to do what they want and not feeling like they are being bossed around by bigger monkeys. "Equality" is a matter of ensuring that the low status monkeys don't feel too low status.
As for "democracy" - well, it turns out that monkeys are generally happier living in industrial economies (with their abundant iPads, cappuccinos, etc), but that such economies require huge centralised bureaucracies to run effectively. The theatre of frequent elections is a convenient way to make every monkey feel like an alpha monkey whose opinion is important and not simply a well-pampered slave.
Both the first year college students with their "laughably simplistic definition of democracy" and "Rawls, Dworkin, Gutmann, Thompson, Bohman, Dryzek, Young, Mansbridge, etc. -- and of course Habermas" with their highly nuanced definition of democracy are in the same category as people discussing programming language theory on the Haskell mailing lists. They have a fun intellectual pastime, and all power to them. But the latest mind-expanding discoveries in category theory have no effect on actual developers maintaining crappy PHP code. (The best they can hope for is that some enlightened and energetic project manager decides to let them rewrite part of the system in Rails.) Likewise, the latest advances in democratic theory have no impact on the people staffing the enormous bureaucracies which run advanced economies. At least the Haskell guys can write Tetris apps in 4 lines of code to show off. It'd be cool if Rawls would gather 100,000 followers to some private island to test-drive his own political system, but it's unlikely to happen. (On a side note, did you hear that seasteaders are evil fascist brogrammers and that charter cities are neoliberal colonialism?)
I'd actually be glad to hear you correct me and tell me that no, actually most Western democracies hand out books by the authors you cited to civil service employees, who hold regular workplace seminars on how to best implement such ideas and bring real democracy (tm) to the world.
EDIT: I realise that I never responding to the grandparent question about freedom and democracy. Well, there are many forms of "freedom" and democracy is certainly compatible with some of them. But I note that democratic states, lacking strong leaders with ability to make more than token cuts to government spending, tend to show a monotonic increase in the number of government departments that decide to regulate ever more and more aspects of life. The thing with regulation is that every individual item of regulation sounds sensible (how can we let people get away with poorly fitted child car seats? the humanity!) but over time people forget that a) they survived perfectly well in ages past when governments tended to leave shit alone and b) they were actually much happier being left free to take their own risks and make their own stupid decisions than have someone prevent them doing so.
An even bigger issue is the fact that if you are a paycheck employee (especially if you have a mortgage, debt and a family) you are in many ways a comfortably-off serf. An ever-growing government takes an ever-growing share of your salary, and since taxpayers are close to being an electoral minority in many countries (did you snark at Mitt Romney's 48% comments?) you are likely to spend ever more of your limited time on Earth working hard to fund TSA agents, drone strikes and the healthcare of aging pensioners. An anglo-saxon freeman had more personal autonomy. At least if you're reading this site you can make plans to build a bootstrapped passive income and move to Thailand.
In regards to paternalism (laws regulating personal safety, nutrition, private health, family relations, etc...) I also believe Singapore tends to fare worse, even if it's manifested in different ways (e.g., there may not be laws against trans fat, but there is compulsory military service, near impossibility of being allowed to live alone in an apartment, extreme difficulty of private car ownership -- which moots the discussion of car seats, etc...). As I a firearm owner, I find California (where I live) and New York gun laws to be idiotic -- but I'm pretty sure my "collection" (couple of rifles and a pistol) would mean death penalty in Singapore.
I think one place where you may have a point is the case of entitlements: it is indeed rare for democracies to have significantly cut some aspects welfare state, namely middle-class entitlement like medicare and social security (welfare programs for the truly poor do get cut frequently, but they are actually less fiscally burdensome than the middle class entitlement).
However, there have been cases of other regulations being significantly loosened, e.g., airline deregulation is something I am quite grateful for.
> people discussing programming language theory on the Haskell mailing lists ... have no effect on actual developers maintaining crappy PHP code.
Interesting observation, and yeah, it definitely smells like Marx. But I'd say it's too early to reach a conclusion like that. It's not unusual for mainstream philosophical ideas of X'th century to have little impact on the real world until well into X+1'th century or even later, and that's under favorable socioeconomic circumstances.
Similarly, programming language theory debated on the Haskell lists tends to "trickle down", after a while, into various other languages and frameworks. 10 or 20 or 30 years later, someone writes a PHP framework that is indirectly inspired by some of them. It takes time, that's all.
I'd be very surprised if political ideas developed in the 1990s, for example, came to fruition anytime before 2090 or so. And the same applies to the neoreactionary ideas of the 2000s. Even if they're as promising as their advocates say they are, it's going to take no less time to port them to the real world. So I don't think your impatience is justified.
> a) they survived perfectly well in ages past when governments tended to leave shit alone
Ah, the usual baseless romanticism about the past. This is what I find the most disagreeable about neoreactionaries. If you want to build a better future, leave your unrealistic notions of history at the door.
> b) they were actually much happier being left free to take their own risks and make their own stupid decisions than have someone prevent them doing so.
Did you actually go back in time and ask them whether they really enjoyed it? Or are you just trying to force everyone else to be "free" (hello, Rousseau) regardless of whether they want to be?
I don't have any problem with a bunch of consenting adults who want to build their own country in the middle of an ocean. It's their money and their own lives to spend as they see fit. But I don't think anybody has the right to drag a single non-consenting person into a copy of Plato's ideal city.
Most people are just fine being comfortable serfs in an industrial society, whether you like it or not. And that's what really prevents the speedy implementation of any political philosophy, whether yours or mine. As I see it, you're not really trying to fix this issue, but merely rewrite history to make it look like a non-issue. It's a fascinating intellectual exercise, but good luck getting your rewritten history merged into Upstream Reality.
The whole "let's have lots of micro-states with easy exit" condition proposed by these advocates here sounds borderline quasi-plausible, IF somehow you could get that going to begin with (not bloody likely)... but even from a purely economic perspective, the transaction costs in choosing a new place to live and moving there are very high, so one would suspect this layout would lead to inefficient results. (and that's economic efficiency, which includes your overall well-being.) And who enforces that you get to up and leave whenever you want, anyway? The other micro-states, using WAR?
A polycentric legal order would have people living in one area who might subscribe to any number of different private security and arbitration firms.
Perhaps you could say their different agencies come to some sort of an agreement in regards to disputes or conflicts between the laws subscribed to by different people. But where such agreements exist they would be made for the mutual benefit of the corporations and not necessarily their customers. To me the end result still looks a lot like a state, just one in which cartels stand in for governments.
The big problem with the micro state idea is military power. Much of the stability apparent in the modern world is really down to the military might of regional powers. Leaving libertarian fantasy land of peacefully trading small states, what seems more probable and historically accurate is feuding for supremacy by any means.
Despite all the computer oriented techno wankery around here, the biggest value of the continental United States is still the Mississippi watershed. Anyone who controls it will be a world power. You can't realistically break it up into stable micro states.
Now it is true that a right of absolute personal freedom is incompatible with democracy, but it is also incompatible with pretty much all other forms of political structure, not to mention most physical laws, the existence of birth and death, and everyone else's right of absolute personal freedom.
Also, about the 'easy exit' conditions, I do wonder who is going to tell the royals to stick to the conditions if they decide to ban folk from leaving a particular state.
Obviously any sort of power, democratic or not, is against "freedom" in the general sense. In reality, you need some sort of power structure, so the question is whether the democratic one is better than any other.
The word "democracy" is used a lot. Usually people aren't mindful of what an arbitrary term like democracy represents in context. They have static perception. Unfortunately, due to the way a lot of these subjects are taught, most people seem to grow up believing that [governmental change in support of human freedom/justice] has reached its climax, that the end-all-be-all form of it has effectively been reached. People then fail to care about seeking even the simplest of changes to the system itself. They stay mentally contained to a philosophical box.
The US federal system as it now stands in loose terms, for instance, is a centralized, binary, non-preferential democratic republic. Paired with its form of taxation, this system has resulted in one of the most top-heavy, enriched, powerful, imprisoning, corporate oligarchical-like governments the world has known. Wars of luxury start happening with relative ease, just as they did under more totalitarianism and deluded republics. The feeding frenzy has never been better. As long as its "citizenry" is lulled into believing in an "enemy" and doesn't have to feel the weight of its violent force that affects others, this will continue. They'll keep throwing their own freedom and that of their neighbor down the drain in support of revenge, clinging to the hopes of another election. One of the only ways to conscientiously object peacefully is the withdrawal of funding, opting for social NGOs instead. Even that is a colossal task. A simple nonviolent action against the status quo of taxation may land a person caged.
Neomonarchism:
Neomonarchism as a reaction to a growing [corporate-war-prison-surveillance state (sprinkled with democracy)] doesn't make much logical sense. I doubt most neomonarchists want more freedom. Anyone who wants more freedom and liberation should tread in the other direction: away from these extremely centralized, top-heavy systems of today and yesteryear. To empower individuals more is to effectively disempower the ability of individuals and groups to rule over one another (who rule at the hand of a sword or by laws inherently backed by violence).