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This study explores the role of personality in teacher retention. Specifically, I test whether long-term teachers fulfill either of two dominant cultural myths often told about them: (1) that they are special (noble, self-sacrificing, and psychologically healthy) or (2) that they are practical (concerned with stable employment rather than pursuing ambitious goals and taking risks). Eighty-five graduates of a competitive teacher preparation program with varying degrees of commitment to the occupation completed a battery of traditional psychological surveys and provided rich narrative data. Results indicate that personality variables do predict retention, even over and above school-level variables like urbanity and student racial breakdown. Evidence also suggests that long-term teachers may be psychologically “special,” or have particularly adaptive and generous qualities.