Sure, I'll go back and tell my 12 year old self to do that.
But, actually, I did do that, to some degree. As I mentioned, I would drop hints and talk about my strategies in games, usually after the game, so he could be more competitive and understand how I was thinking about things. That also has a cost on the fun for both parties, though. Smart people can recognize when you're going easy on them. Nobody normal likes being pandered to.