Reads like one of my posts when I was drinking.
I think I know what you are asking at least. A buddy I used to work with was a bookie on the side, a fairly big one. He was actually retired in his late 30's, but kept his job as we worked for an airline and the flight benefits are real hard to let go, especially if your a cheap ass wealthy guy. He's currently one of the top amateur golfers in the state.