This study proposes that stress associated with two kinds of job demands or work circumstances, “challenges” and “hindrances,” are distinct phenomena that are differentially related to work outcomes. Specific hypotheses were derived from this general proposition and tested using a sample of 1,886 U.S. managers and longitudinal data. Regression results indicate that challenge related stress is positively related to job satisfaction and negatively related to job search. In contrast, hindrance related stress is negatively related to job satisfaction and positively related to job search and turnover.