Portia, I think what your SO is saying w/the comment "life is challenging, but I remain optimistic" is the fact that he is finding out that life isn't a box of chocolates. He's finding out that he's still got the same old issues at the end of the day and no matter what he does or tries, the issues are still there. He may also be up against whatever issues he was having at work and has discovered that no amount of counseling is helping in that area. He's still looking at life through rose colored glasses and thinks that the rainbow has a pot of gold at the other end. If only he could find that pot of gold, he would be so happy!
I think you were very wise not to question him about this comment. They have a way of sending out cryptic messages hoping that you are still interested enough in their lives that you'll take that bait. It's his way of checking the temperature of the relationship.
You are doing great! I'm sure your kitty was having a wonderful nap when you snapped the photo. Kitty is one lucky little creature to have you as his/her mom.
Sit quietly, the answers will reveal themselves when you least expect them to. The past is gone, the present is a gift and you need to focus on today, allow the future to reveal itself when it is ready.