This article concentrates on the life of Aaron Director at Lincoln High School in Portland, Oregon (1914–21), and at Yale University (1921–24). Its primary purposes are to examine the juvenilia of Director in order to analyze the evolution of his worldview and to shed light on Director's life at this time through the use of archival and secondary sources. Tracing the evolution of Director's worldview leads to three claims. First, Director maintained that the individual or an elite group of individuals was the catalyst for social change and expressed skepticism toward governing structures as means to make improvements in society. Second, Director believed that open-minded educators who challenged social injustice and prejudice were essential for social and economic reform. Third, Director adopted the critical and skeptical social philosophy of Thorstein Veblen and H. L. Mencken. In conclusion, this essay maintains that the worldview of Director's youth motivated and empowered his postwar efforts at Chicago.

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