letting him own his learning

Friday morning. 9 yo is reading on the couch about the Battle of Gettysburg. He is excitedly telling me who was where and what they did, and who won and how and what losses were on each side. I call him to have breakfast. Since it's Friday (and I still have to finish cooking for Shabbos), we are debating whether he should start on long division in math, a new topic. He is wary of it. I ask whether he knows divisibility rules, and he tells me the one for 5. I tell him the one for 3, and he is trying it out. He has seen me do long division, and since I'm feeding the baby, I am more telling him which numbers to put where rather than making him do it. He is very excited by this new rule, and he has to try it out on some numbers from his head. I am watching as he is doing long division on his own, and then he checks it through multiplication. Then, as I am writing down the rest of the list, he starts figuring out gemmatrias of the names of all people in our family. He discovers that 7 yo has the biggest one, and aba (daddy) is the smallest.

After all this, it is kind of silly to say "nu, get started on your learning already".

He is enjoying learning. He is on his own schedule, and he has his own agenda. As the years go by, I know that his agenda will totally overtake my agenda. If I am any good, his agenda will include subjects which are important to me (Torah learning, for instance), and subjects which he is passionate about (history categorization; Pokemon/video games; imaginary world maps). If I am very lucky, his subjects will help him figure out a path in life. And, with G-d's help, he will be happily pursuing that path.

It's so simple that  I am hyperventilating: what about higher math? English grammar and composition? Gemara? What if he ends up living on my couch in the basement? What if he will be ill-prepared for life?

But what if he got his experimentation and bumps on the road early on, instead of waiting till college? What if he has a head start to figure out who he is? What if he gets a chance to listen to himself and figure out what makes him tick instead of marching to someone else's beat? What if he learns that challenges are surmountable? What if he learns to think instead of waiting for someone else to tell him what to do? This sounds like acquisition of life skills.

I am oscillating between structured learning and unschooling. Towards highschool years, unschooling has to take an upper hand.