I don't see the songs as uplifting, but rather as trying to make lemonade from lemons, or whatever. When I listen to them, I understand the context. I don't like to pepper songs with my own experiences, though.
Nick Flynn is another writer I admire - his fragmented sections, his playfulness with genre, his urgency. The palette in his work is his style, a voice that is singular, and that's what I think writers should strive for, to have a style and a voice that is only theirs.