The short story "Winter Dreams" by F. Scott Fitzgerald tells of a middle-class boy from Minnesota named Dexter Green. He has a dream of being wealthy and well-respected. The story follows his life for several years as he caddies for golfers at a golf club, attends college, and then finds wealth in the laundry business. One of the main focuses is on his relationship with a gorgeous socialite named Judy Jones who he first meets at the golf club when she is only 11 years old.
Dexter's motivation for being a caddy, as explained at the beginning of the story, is to make "pocket-money." His father owns a prosperous grocery store in the town of Black Bear and presumably takes care of Dexter's basic expenses. This means that Dexter can use his caddy money for whatever he wants. In contrast, some of the other caddies are "poor as sin" and live in one-room houses. In such a situation, their caddy money would be essential and they would not be able to even think of quitting.
However, one of the story's essential plot points hinges on Dexter's loose attachment to his job. Because he is merely earning pocket money and his income is not essential to the survival of his family, he has no real need to work and can quit his job if he decides to. Young Judy Jones shows up at the golf club and calls for a caddy, but after seeing the way she treats her nurse, Dexter refuses to do work for her. He quits rather than act as a caddy for Judy because he does not want to be in a position of subservience to her.
As Fitzgerald puts it, "Dexter was unconsciously dictated to by his winter dreams," which include being wealthy, talented, and prestigious. These dreams become the motivation for many of Dexter's decisions as he proceeds through life. Caddying for Judy would not have fit with his ambitions in life, so he sacrifices his job for the sake of his long-term goals.