I get the impression that it is an epitaph on his career and life, looking back, giving his thoughts, reminiscences and opinions. He seems satisfied but still rebellious at heart. Just my opinion though - others may well see it differently.
I picked up this album yesterday and I just listened to it this morning and I think it is just great. I really enjoy the stripped down production. I think this is the best kind of country music. I am really impressed. I would not have picked it up if you folks hadn't been discussing it here.
It's indeed the old road with the same three chords and touching lyrics - and when it came to "go break a heart" I was inspired to find my own old road and found 10 simple tunes of longing on the sidewalk.
