The present study employs a moderation model to examine the relation of various sources of stress emanating from the role of the school superintendent to personal well-being and the additional effects of personal coping resources and social support. Results of multiple regression analyses using a sample of 117 school superintendents showed that utilizing personal resources of rational coping and taking time for personal care activities outside of work contribute significantly to well-being, in addition to the negative effect of occupational stressors. Rational coping also moderated the relation of stressors to well-being. Implications of the findings are discussed.