Well, Since You Asked

How does Ben Gibbard feel?
I think you should read the article i have that he wrote about his life and Narrow Stairs.
But until you do i'll just give you a jist.

He recognizes that he is never content, and severely doubts that he ever will be. He dwells rather heavily on possibilities (which includes all the missed ones) so it's rare for him to not see someplace better than his current one.

He also believes that there will be nothing greater in the world for him than his music and what he's created, as well as the other things he experiences. No love will ever trump the one it has for him and that he has for it (because love is necessarily reciprocal).

You truly do need to read that article.
I'm going to tonight, and i'll throw it your way later.