We developed and tested a model linking proactive personality and career success through a set of four behavioral and cognitive mediators. A 2-year longitudinal design with data from a sample of 180 full-time employees and their supervisors was used. Results from structural equation modeling showed that proactive personality measured at Time 1 was positively related to innovation, political knowledge, and career initiative, but not voice; all measured at Time 2. Innovation, political knowledge, and career initiative in turn had positive relationships with career progression (salary growth and the number of promotions during the previous 2 years) and career satisfaction. Interestingly, voice had a negative relationship with career progression. We discuss practical implications and future research directions for proactive personality, extra-role behavior, and careers.