This research investigates the relationships among risk, corporate performance, and managerial agendas. The primary goal is to understand how relative levels of performance are associated with relative levels of risk taking. Individual managerial agendas are used as indicators of risk taking, and these indicators are compared with other measures of corporate risk. Secondary questions relate to the significance of industry life cycles, types of strategies, and the perceptions of senior managers. The research design is based on selected focused comparisons of risk, performance, and strategy of eight firms. Results indicate that managerial attitudes and perceptions of risk do not directly correspond with financial and economic notions of risk. While poorer performing firms may seek to take risks, they appear to be constrained by internal factors. Higher performing firms may seek to avert risk, but their apparent risk aversion seems related to their recognition of external uncertainties.