That he's talking to you about some of his fears is great. Getting old(er) can be scary enough, given the economy, well, I'd be preaching to the choir I suspect.
It's good to hear that the evenings are more relaxed and you've been included in plans more. Mostly I like that you are feeling pretty good from the sounds of it.
The career goals will be helpful on alot of levels. I hope you achieve more than you're aiming for.