The Loser Waits on a Superior's Mother

The Complete and Total Loser is at work, doing his pointless retail job. A woman, in her late sixties perhaps, comes in and buys a few items. The Loser takes her credit card and, before swiping it, sees that she’s written “Ask for I.D.” on the signing strip. He does so and notices that her driver’s license shows that she has the same hometown as the one he grew up in.
“I grew up in W_____ myself,” the Loser says as the sale is processed. The woman asks which part. The Loser tells her and agrees with her when she says that’s not really W____ but the fringe and that the primary similarity was the ZIP Code. Then he mentions that the center of W____ was nonetheless close to him and that he worked at the local movie theater for several years while in college.
The woman says that her son, too, had worked there cleaning the theater after closing and, with a mother’s pride, adds that “Now he’s a successful journalist.”
The Loser puts her name together and realizes that her son is more than a successful journalist; he’s among the top tier of American journalists working today, a well regarded New York Times staff columnist, author of a well-reviewed book on current culture and a frequent guest on the Sunday morning news shows. He's known for being a conservative but who sees the liberal point of view. He is pro gay marriage, pro Obama. 
The Loser was a journalist, too, but not a very good one. He worked for a local weekly and did well enough at that level but failed to get promoted reporter after a year as an editorial assistant at a larger news organization. Sometimes he tells himself it was because he started that career too late in life (38) or didn't play the political office games well or lacked confidence in his ideas. But he knows that ultimately he just wasn't good enough.