The things I said to him that day are things I'd never before articulated outside of my own head, because they seem too obvious to me to be worth saying. I said them in this case because I was exasperated, couldn't think of any other reason he seemed to be running directly into a corner over and over again, and wasn't having much luck with asking simple questions. I was expecting him to respond with, "Duh, I know that; the actual problem is x," which would finally allow access to the actual problem.
But no, the truth is that sometimes very smart people intent on winning the game simply never learn how to use the controller. So, just in case you happen to be button mashing at the moment, here are the things I said that have helped him take much more control of his life.
You have values. Winning means fulfilling those values. Fulfilling values requires identifying and accomplishing causally relevant goals.
If your goals have not already been accomplished, it means that the universe is not in your preferred configuration yet. Since there are a whole lot of possible configurations of the universe, unless you have extremely general goals, the odds are pretty small that the universe will just happen to end up in your favorite one if you simply wait. That doesn't mean, "Don't get too set on specific goals, 'cause you'll probably be disappointed." It means, "Don't wait." The basic game mechanics consist of learning to manipulate causal chains to increase the odds that the universe ends up in the configurations you like, and doesn't end up in the configurations you don't like. Manipulating causal chains means trying to understand them and then reaching out and actually acting on them accordingly.
In other words, figure out what you want, figure out how to get it, and then do that.
It sounds so obvious that I'm embarrassed to say it. But people really do seem to spend most of their time not doing this. They just sort of stand around waiting and hoping that things will go their way. They waste a lot of time lamenting the cruelty of fate when bad things happen, and feeling blessed when good things happen. When Karma shits on them even through they tried really hard, they feel helpless instead of wondering whether they're trying the wrong thing.
So when you're stuck in a corner, make sure you're holding the controller and not button mashing: Figure out what you want, figure out how to get it, and then do that.