Sargon: Five False Assumptions of Liberalism
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He used to consider himself a "classical liberal" and still says he "defaults" to that position but no longer considers that a hard philosophical position.
Reading between the lines, I think he's looking for pragmatic ways to make classical liberal assumptions hold to the maximum extent possible.
I think he's developed a much more complete world view where freedom has to be accompanied by responsibility. The free-er you are, the more responsible you are for maintaining your own moral standards.
The next step is understanding who can thrive under freedom… and who cannot.
That's a really good point. Some people are definitely sheep that need to be led, and most of it because they were never made to grow up in a nanny-state society.
He's also pointed out that you're never really free from hierarchy or responsibility. As a "free man" he's obligated to his wife, children, and community.
And they are obligated to you. Well said.