Dexter dreams of becoming a famous golfer and playing golf against those for whom he caddies now. By playing against them - and beating them - he sees the fulfillment of his deram. He will be successful.
His sense of deprivation does not subside when he becomes wealthy because there is always something more. A wonderful young woman, for instance, becomes engaged to him, but he breaks it off to pursue Judy - a wealthy young woman who he had met in the past. He is unable to enjoy his success because he always feels he has something else to prove and wants more.
Even when Judy proves to be shallow and selfish, Dexter is unable to break with his imagined vision of her until the very end when he is told that Judy has become a housewife married to an alcoholic husband and is no longer the beauty she once was. This becomes a reality check for Dexter who realizes that there really is no stability in the dream he has chosen to pursue.