I'm happy to hear your academic life is positive. To me, fall is very hard due to the startup of the school year. When that's combined with trying to accomplish personal goals, it can feel overwhelming.
There was a boy, 13ish, on one of my rivertrips once, and we went for a hike together. Up in one of the side canyons, he found a frog next to a pond. The frog was recently deceased and he started poking at it. I asked him if he'd ever dissected a frog and he said that he had, but he hadn't paid much attention in class and didn't do very well on identifying the organs on the handout. I suggested we dissect the frog and after a little hesitation, he agreed. I gave him my pocket knife and he hunkered down in the sand and went to work on the frog. It became an exploration. He'd point at things and ask me what I thought it was. I'd say I wasn't sure. We'd both stare and poke at the thing until we puzzled it out.
He had a great time and I'm sure if he'd been given the same handout, he would have aced it.
Point is, you can't give H things to read and expect him to be hit with a great flash of insight. He has to come to it on his own or he'll never accept it.
I like FG's lifeguard analogy, but as a former lifeguard, I got pretty sick of people who went into situations where they never should have been or people who wouldn't take the smallest amount of responsibility for themselves. Things happen, it's true. But you can't make a life out of crises.
Sounds like you're rebuilding your wall. I am too, or building anyway. Careful though. Walls are generally not good things. They inhibit you as much as others.