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In Death of a Salesman Willy holds on to a corrupted view of the American Dream. The American Dream is that of one where if you work hard, you will become wealthy and have no problems. He looks at the idea of the "self-made man" as his ticket out of his current mundane life and job. He looks at myths and stories about tycoons like Henry Ford, Carnegie and Rockefeller; however, by the play's setting (1940) the American Dream as well as the job market has shifted. Salesmen like him now require special training, not just a desire to work hard and the gift of persuasion. He sees his brother and other salesmen succeeding, so he fully believes one day he will too. Because he does not achieve his version of the American Dream, he has failed in his eyes.
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