He originally wanted to be involved in journalism and did get his lucky break by getting accepted into a newspaper. He started as a copier and errand boy, down in the dregs of the company, and when he finally got his big chance to prove that he was a writer, he blew the story terribly. Rather than be faced with staying an errand boy for the rest of his life as the memory of that story hung over him, he quit the company. Unfortunately, the only other work he could find was with a catering company working deliveries. That's two lucky chances he blew, and he doubts he'll be granted any more. The prospect of staying a nobody for the rest of his life drove him to alcohol, making it less likely that he'll be able to do anything about it.
Songs
The Big Rock Candy Mountains