In Arthur Miller's Death of a Salesman, Biff struggles with finding the kind of job that his father believes will bring him success: working in business. Biff has tried to do that. For years after high school, he trudged to work, fifty weeks out of the year, with no upward movement, no interest, and the flimsy reward of a two-week vacation. In Biff's mind, the idea of success—his American dream—cannot be found in working in an office day everyday, all year, but in being outdoors, working without a shirt. He notes that he always seems to gravitate to jobs that let him work outside.
Hap, I've had twenty or thirty different kinds of job since I left home...In Nebraska when I herded cattle, and the Dakotas, and Arizona, and now in Texas...This farm I work on, it's spring there now, see? And they've got about fifteen new colts. There's nothing more inspiring than the sight of a mare and a new colt.
Biff believes that he should be doing something else, just as his father expects him to, but Willy is no more satisfied with his life: he lives in a dream world. However, his expectations of Biff do not allow that Biff would work on a farm—and this causes Biff great unhappiness—a total lack of self-fulfillment.
Hap isn't satisfied either. He has a job; yes, he's making money—but he's struggling with his place in the working world as well, seeing no way to demonstrate true success (as Willy would see it). He works for a man who makes a great deal of money, and while they get along—Hap says, "He's a good friend of mine..."—all Hap can do is wait for his manager to die, for the manager is doing well for himself, but there is no upward mobility available to Hap. Hap's idea of success is:
...I think of the rent I'm paying. And it's crazy. But then, it's what I always wanted. My own apartment, a car, and plenty of women. And still, goddamit, I'm lonely.
While both Biff and Hap seem to know what they want (and the idea of success of each is very different), somehow they are cursed with a sense of failure. Both feel inadequate when they pursue what they want. Again, I believe that Willy's expectations follow them wherever they go, and unless they are doing what their father believes they should be doing, neither is satisfied with what he has or what he has achieved.