Willy's unhappiness stems largely from his misinterpretations of the American Dream and his inability to reconcile the way the world actually works with the way that his version of "promise" dictates that the world should work. Believing that being not just liked but "well liked" is the key to financial success, Willy lives out his life without a plan, dwelling on the past when he was already a failure but his children seemed poised to become successes based on his world theories. Miller implies that the real secret to success is luck in having natural talents, an ability to work hard without trying to take short cuts with acquaintances (like Bernard did in high school while Biff was "turning up the charm"), and/or a willingness to take risks in the business world (like Ben did when he went into the jungle). Willy truly has none of these talents nor can he see despite the constant examples that this is the key to success. He repeatedly asks his brother Ben how he became a success. Willy cannot plainly face the truth because it means that he missed the greatest opportunity of his life - to go with Ben into the jungle.
On a deeper level, however, Willy knows that he is a failure. That is why he obsesses over Ben's greatness and Biff's weakness. But Biff is not as wretched as Willy. Biff is alone in the Loman family of seeing a plain counterexample to Willy's claims of success - and not denying it. Biff realizes that going to play football at the University is not the right career path for him. The attempts to make connections with the important people he is destined to meet at Penn State would surely not help Biff anymore than they helped Willy (and Biff would definitely not succeed in the academic manner of Bernard). While Willy pines over the seeming pitiful aspect of Biff's "giving up," he is in fact doing Biff a service by liberating him from the "worship" of a troubled, washed up man (Willy). Although Biff is never truly happy because of the feelings of disappointing his father because of a lack of material success, Biff is, at least, spiritually at rest and honest with himself about how he is technically a failure.
Years later Biff repays the service, by attempting to bring his father out of his delusions and into the same morose but truthful reality that Biff inhabits. After Biff remembers that he was never a salesman for Bill Oliver, he tries seemingly unsuccessfully to convince Willy of this grave fact. Biff feels compelled to persuade Willy that he, Biff, was never a salesman (and never successful) in order to free Willy from the increasing insanity that stems from the increasing disparity between his dreams and realities. (When Willy was younger it seemed possible that the best of life was yet to come but as Willy ages he realizes how truly sorrowful is the life of the poor man who believes the rich man's hype. Once Willy's sons are proven failures, Willy cannot simply put his hopes for happiness onto Happy and Biff but must fabricate a world where they have already achieved success. Thus, the old Willy is not really any crazier than the young one - just as terribly sane. Both Willies need a certain reassurance of the successful lives they lead and convince themselves of their own success by the most economical means, the young one puts success on his children and the old one says that the children are already successful.) Biff is frustrated by the obduracy of Willy but refuses to give up hope that the fantastic lie Willy spins throughout his life can be broken. Willy's suicide is evidence of Biff's success. Finally, Willy can come to terms with his sorrow although he is not strong enough to face alive the lie that his life has been. Willy does, however, seem grateful for facing reality as evidenced by his last magnanimous act of giving Biff the life insurance (although that obviously wasn't the real reason he killed himself).
Willy Loman lead his whole life in pursuit of romantic ideals of beauty, athletic prowess, and "being a guy" as the factors of success. These ideals were so ingrained that when the opportunity for true success faced him, he ignored it. From middle age on, Willy is forced to face his failure of philosophy. His inability to do so until the very end of his life creates the dreamy delusions of the attainability of the American Dream that Willy is relegated into believing in.
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