I think this is about someone who battles depression. People say he's the luckiest man, maybe because they are either encouraging him or to them, his life seems quite nice. But to himself he's constantly thinking of ways not to lose. He doubts himself a lot. He is almost jovial about how people says he's the luckiest man. If you, as most people have, gone through depression you know no one quite "gets it" and it can even be laughable at times.
I think this is about someone who battles depression. People say he's the luckiest man, maybe because they are either encouraging him or to them, his life seems quite nice. But to himself he's constantly thinking of ways not to lose. He doubts himself a lot. He is almost jovial about how people says he's the luckiest man. If you, as most people have, gone through depression you know no one quite "gets it" and it can even be laughable at times.