When upwardly mobile persons are promoted from lower, individual contributor roles to higher, managerial roles, they are confronted by the challenge of negotiating a series ofl35-degree or shifts in their careers. Those who make the complete journey must traverse five pathways and four crossroads. These critical career crossroads consist of discontinuous and unprecedented changes in the role responsibilities and accountabilities to which managers in transition must respond. At each crossroads, people are confronted by a triple challenge: letting go of anachronistic responsibilities and competencies, preserving those that continue to be useful, and adding new, discontinuous responsibilities and consequences. Managers in transition can cope with these demands by making adaptive changes in their preferred activities, behavior patterns, and style. A detailed examination of the unprecedented discontinuities that ambitious, upwardly mobile managers must bridge is presented. The adaptation process that is required at each career crossroads is described, followed by a detailed set of recommended shifts in behavior patterns for the future executive at each crossroads.