I have a great deal of sympathy for that “damned if do, damned if you don’t” problem that really engaged parents describe, and I feel like I have observed this issue with an outsider perspective. My spouse and I live in SF now (I’m a programmer, she’s an engineer) but we’re not exactly from here in either the geographic or social-economic sense. She grew up in northern Idaho and Montana, I grew up in Alaska. Her parents were military and mine were sort of hippies, and we both had more or less what would now be considered a free-range childhood experience. I think I would have preferred to be raised the way you describe.

I had some pretty seriously bad experiences and set backs that were probably unnecessary, and that I now understand many parents would have intervened to prevent. I would gladly trade being street smart in my twenties for having spent more of my life the way I get to spend it now.

We were moderately more interventionist with my stepson, but he doesn’t want to be an engineer or an academic, and we’re not trying to make him. I think one of the toughest things about parenting late teens/young adults is that whatever experience or skills that I have don’t necessarily have any bearing on their preferences or goals. My parents didn’t really understand what I needed for my career because it wasn’t part of their experience, and I don’t assume I will understand how best to achieve the goals of young people interested in fields that aren’t like mine. I try to figure it out collaboratively, and often refer young people to others who are more experienced in the desired area.

I hear people talking about class in this conversation, in the sense that people might need to be prepared for different things. The things is, you’re starting from where you are, not where someone else is. And who’s goal is it to be downwardly mobile? Who wants to spend their youth learning things the hard way by being isolated, unprepared, and having bad shit happen to them for no reason? A comment down thread remarked that if you “hang out with some poor kids and get into fights, then they'll really be prepared for anything.” This won’t prepare them for “anything”, it will prepare them for fighting with poor kids, and then probably being interfered with by the state.

One of my favorite younger friends had an upbringing more the like the kind you have given your kids. He was home schooled, studied Jujitsu, went to U. Chicago, and last I heard from him, was working in fintech in New York. He once managed a fighting retreat from a gang-initiation/mugging in south Chicago. This after being home schooled in a small university town. That’s certainly better then I could have ever done, no thanks to my free range parenting.

I sometimes have a sensation of class dysphoria. A construction boss once told me: “You’re kind of daydreamer. You should get a job using your mind.” It wasn’t a compliment, and that was my last day on the job. My parents (and most of my grandparents) were college educated professionals of the middle or upper-middle classes. I am now told I look like a convincingly San Francisco programmer shaped object, but I feel like I don’t fit in anywhere. If I drink too much I get a Texas accent. I don’t complain about the cops anymore (my spouse told a black friend I don’t like to deal with cops, and the friend assumed I was black; I’m not). I had to ask what the foie gras was at the office Christmas party. I thought it was cheese.

I have seen a lack of autonomy and initiative in some of the young people I have met here. My spouse recently supervised a high-school intern who had wealthy (even by valley standards, I believe) and very involved parents. She was congenial, intelligent and highly achieving but it seemed to me that she had a peculiar inability to consult her own genuine preferences, or synthesize her own opinions or plans. I find this condition rather alien, and I suspect that it is what people are concerned with when they complain about over parenting. I think it is possible and desirable to provide structure and generous assistance to young adults without telling them what to want out of life. Obviously, this is value statement, and I reservedly respect values differences in this area. The intern’s parents seemed to believe that there are better and worse life goals, and the the correct goals for their daughter to have were to attend an ivy, and then enter a class appropriate engineering or design career. It’s not at all clear to me that if that had done everything the same except for telling her what goals to have, that she would have more natural initiative. Maybe she would have, or maybe she’ll learn that after she already has high status college degree she doesn’t really want. In the worst case, is figuring that out when your 25 really so bad? I guess I’ll never know, but it sure sounds better then what I was doing at that age.