Little is known about classical Christian schools and their leaders in the United States. This study describes the headmasters of such schools and their sense of job satisfaction, job efficacy, and career aspirations. Numerous significant relationships among the variables were found, including between job satisfaction and a headmaster's relationships with the board, faculty, and parents. A regression analysis indicated that 45% of the variance in their sense of job satisfaction was predicted by transactional leadership qualities, relationships with the governing bodies, classical pedagogy, and career aspirations. (Contains 1 figure and 6 tables.)