Tyranny of the minority demonstrates that an overemphasis on individual liberty without a sense of a community WILL fail. The blood of the last century demonstrates that central control will be seized by the psychopaths
I really don't know the source of the quote - I think it was inspired either by a comment or a podcast and summarized by me, but it's pithy, and it's true. It encompasses both the failures of an overemphasis on atomic individualism, and an overemphasis on defaulting to the government as the source of power. Atomic individuals are susceptible to the tyranny of the intolerant minority as described by Taleb, and sociopaths will lie, cheat, and steal to gain the power over others when power gets too centralized - and it doesn't matter if it's "government" or companies-as-government.
I've mentioned before that an implicit assumption in the libertarian "marketplace of ideas" is that the people in the market are interested in truth and quality, not pretty lies. Unfortunately quantity has a quality all its own, and whether those invested in pretty lies do so by the vote or by raw force, they can shun and shut out, if not kill, those standing in the way of what they want.
Ditto goes for democracy and free governments vs "socialism" or other forms of tyranny. If you care about freedom, and not having the masses voting themselves your hard-earned paycheck. For democracy to work, the majority of the people need to share the vast majority of the core assumptions.
What if you come from a high-trust live-and-let-live society where all most people want to do is be left alone to enjoy the (good) consequences of their work, help out their neighbors, borrow a chainsaw, loan the mower, and everybody expects everything back in as good shape as they lent it, and the number of busybodies is relatively low? All of a sudden you have entire neighborhoods full of noisy people who don't act like you, think you're a chump for loaning the mower, culturally consider anything not gated or nailed down fair play (spend any significant time in Miami, or just trust me), and are perfectly happy to vote themselves a chunk of what's in your pocket? They don't care about following the rules in the first place.
Or people who think guns are icky, and are perfectly happy to help themselves, or their less fortunate brown pet projects to your money, and think that you being in a position to effectively say no is a bad idea?
Or those same people who think it's perfectly OK to kill a baby because it technically hasn't been born yet. Yes, we find ourselves in the ridiculous position that in parts of the US a baby could have been deemed "human" on a Friday, but isn't, because the delivery was rescheduled to Saturday from Thursday.
And they start outnumbering you.
That ballot box isn't going to help much. Especially as that latter set of busybodies can't stand leaving people alone if they're "doing it wrong."