Holland’s (1985a) typology of persons and environments is outlined, and support for the theory as an explanation of stability and change in careers and work satisfaction is summarized. Studies show that people flourish in their work environment when there is a good fit between their personality type and the characteristics of the environment. Lack of congruence between personality and environment leads to dissatisfaction, unstable career paths, and lowered performance. The results of recent research designed to strengthen the explanatory power of Holland’s typology and link it to the Big Five personality factors is described. Speculations about the application of the theory to future careers in a changing economy are offered.