The question, "What is your biggest problem with libertarianism," could have easily fallen on deaf ears. The answer, however, exposed the kernel of thought that most troubles libertarianism: children. Indeed, the moral status of children and an accompanying theory of paternalism would be a huge difficulty for an ideology whose favorite epithet is "paternalistic."
Because of its allergy to paternalism and coercive restraint upon the individual, libertarianism doesn't give us a good story about how we should form or educate children (in the literal sense of "bringing out" or "bringing through" children into adulthood) because libertarianism is so individualistic. So someone like Walter Block, for example, is at his most comical defending the employer of child labor because his theory of education is so hopelessly barren. A child becomes an adult in Block's view by acting in a way that befits an adult, e.g. selling his labor to an employer for a wage and living apart from his parents. The transformation of child into adult is a kind of "immaculate conception" whereby the child wills himself into adulthood, where the very performance of leaving home to seek employment serves as proof of childhood's end. There is no theory of education here beyond the single, formative, self-begotten action that Block calls "adult homesteading" and allows children to "fire their parents" when they become too "onerous."
The comedy of Block's effort results from shoehorning an intransigent feature of human life into a constrictive ideology of individualism. But childhood isn't reducible to the vocabulary of individualism because children must be educated, and education involves, well, coercion and indoctrination. What is more, education involves more than just parents. It involves a community and a culture--or a theory of what a community praises and blames. And the need to educate the next generation, or to answer the question "What will we tell the kids?" justifies the intuition that there are collective goods of moral importance in addition to individual goods.
Leo Strauss is said to have quipped (and he was a man of few quips) that all political philosophy is about education. I understand this to mean that the central motivation in political philosophy's search for the best regime is the thought of how we want to raise or rule our children. Libertarians might better understand traditionalism, conservatism, and liberalism if they recognized that paternalism, rather than some misplaced political gesture, is in fact the central subject of politics.
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