I have come to the conclusion that I either did not unschool properly, or it is just not true that all kids will learn what they need to learn when they see the need, because ds just cannot seem to get past the remedial math he needs to get to the certain class he needs for college credit. He is 19 years old and desperately wants to transfer to a 4-year college as nearly all of his more traditionally homeschooled and ps friends have already done.
When he did not want to do any traditional math, I respected that wish. When he wanted to immerse himself in gaming I allowed and supported that (and told myself it was what he needed at the time), when he did not want to write papers for his homeschool co-op classes, fine. He would do it when he was ready. When he said he wanted to begin remedial math classes at the cc without having done much at all in our unschool/homeschool environment, that's what we did. When he started to have troubles with math, we got him a tutor. He tells me that the difference between him and other students at the CC is that he never learned how to study, how to manage homework, how to take tests, even though I tried to expose him to these things through various homeschool classes.
I have come to believe that unschooling is great for young kids who still need ample time for free play, it also can be great fro older kids and teens who are highly motivated and passionate learners. It may also be fine in families who really are truly OK with their kids taking all the time they need to get to where they want to go, even if it takes them well into their late teens and twenties being all-night gamers in their basements. We do not have the means to support that route indefinitely.
There are no blanket truths in unschooling, it really depends on the kid and the parent needs to be savvy enough to recognize when continuing on this path is not in their best long term interests. I tried to believe that it was OK for ds to fall well behind his friends because he was not ready, he was learning in his own unique way, I was respecting his right to do that, or who could say where his passion for gaming would lead? I really did *not* believe it, and maybe some would say that is the problem, but I think it has more to do with him making the calls in areas where it really was my place to do it as the parent.