The rhetorical trick that allows free-range schooling to come out on top of conventional schooling in every category is that Oppenheimer never tells us what schooling is actually supposed to accomplish. At various points in this essay, schooling should primarily: diminish angst, inculcate empathy, inculcate content knowledge, empower children to "take responsibility for their own education," and hand down fundamental community values like recycling(!). This is convenient, because when Sudbury Valley fails by one standard, Oppenheimer quickly elevates another by which it succeeds. He meets a student there who doesn't know who MLK was. Well, that's ok:
One could reply—and the Sudbury believers would—that he will figure out somewhere in his adulthood who Martin Luther King Jr. was, and will know as much about him as the rest of us do. That as soon as he enters the workforce and gets that day off, he’ll want to know what it’s all about. That the habits of citizenship learned at Sudbury practically ensure that he’ll want to relate to his fellow citizens with empathy and candor, so if he discovers that there’s a man who’s a hero to many fellow Americans, a man whom he knows little about, he’ll take it upon himself to learn.
One could also reply that a Sudbury student with a passion for literature or American history could graduate with a knowledge of civil rights, and the milieu of the 1960s, deeper than most college students have...But the Sudbury advocates would also say that even if a given student never picks up on some bit of knowledge that we civilians deem essential, then so what? The tradeoff made at Sudbury is worth it: Every child will have some blind spots—and don’t children in most public schools, and even the best private schools, have blind spots?—but Sudbury children have a radical sense of empowerment and responsibility for their own education.Our education is not about learning anything, but about making you into the kind of person who could potentially learn things, if you ever get it into your head to be "passionate" about them, or someone helpfully informs you that they exist in the first place. I wonder, isn't that kind of the default description of every human being without any kind of schooling at all, free-range or otherwise? And if you never get around to activating your potential to learn? Well, that's ok too, because Oppenheimer can't remember most of the stuff he learned in school and he's doing fine in life, so it's probably not that important for current children to learn stuff and better for them to come away "radically empowered" instead. So the argument shifts from the claim that children learn content better under free-range conditions because they're self-motivated or unstressed or self-governing, to the wholly contrary claim that learning content is not the aim of education anyway.
This is the kind of mushy-minded progressive education "reform" talk that is characteristic of parents who can't decide whether they love their children or their "values" more. Consider Oppenheimer's prediction that, "I will someday have a child for whom the local public school is not working." What does that mean - a school that's not working? Oppenheimer doesn't say much about what a "working" school looks like, beyond that the children seem happy in it, so one gets the sense that it would stop "working" when one of his children stopped being happy to attend. At the same time, he wants the school to convey "a complex of values and sensibilities, both canon and custom, that their parents, teachers, and town have concurred on: tolerance, environmentalism, don’t-litter, all people are created equal, and so on." So what if the reason that a school stops "working" for a child is that he begins to dissent from his community's values? Does that mean the school has failed, or the child? Whose side would Oppenheimer take in such a quarrel if the child were his own?
The education of children is necessarily coercive. If children didn't need to be taught - that is, forced to learn - anything by adults, then there would be no need for schooling in the first place, or a distinction between children and adults except in matters of height, and even benevolent cow pastures like Sudbury would be out of business. This basic conflict is heightened when we bring civic demands into the equation, as Oppenheimer has done. Then education becomes doubly coercive - it now demands both individual development and conformity with civic norms; you must learn how the world works and heed the imperative to recycle. This is the basic conflict that Oppenheimer hopes he can evade through some elusive curriculum that requires nothing from children but delivers everything to them. Sudbury demands little, and he discovers that it gives little in return. Certainly, it sounds like a pleasant enough place for children to pass time with one another, but then so is an open field. And there may indeed be some educations compared to which frolicking in an open field for 12 years would actually be preferable, but Oppenheimer is not comparing Sudbury to getting pounded every week by one's classmates in some chaotic Anacostia middle school. So he has to find ways to massage its pittance into a fortune - empowerment, egalitarianism, other such vaporous terms. If these were really the aims of education, then I wonder why Sudbury tolerates the hierarchy and disempowerment suggested by a "head of school," when surely it's an institution small enough to be democratic in the strict sense.
Oppenheimer is right that all public schools will some point not "work" for their students. All private schools too. The work they do must run against the desires of their students because their goals are communal rather than individual. If your child doesn't want to keep his hands off his classmates or do math problems, his school is not "working for him" when it demands these things of him, but it's not clear that the best solution is a less coercive school. And if you can't have an un-coercive, un-hierarchical school, then the real question is what kind of authority and discipline is necessary, not whether it is.