This article continues a series of analyses using the "theory of careers" developed by John Holland to examine the patterns of student stability and change inherent in the college experience--as part of an effort to understand the satisfaction, learning, and retention of college students. The underlying basis of Holland's theory is that human behavior is a function of the interaction between individuals and their environments. The theory focuses on an assessment of individuals, their environments, and the interaction or "fit" between individuals, and their environments. Three specific assumptions are associated with these three essential components of the theory: (1) people tend to choose environments compatible with their personality types; (2) environments tend to reinforce and reward different patterns of abilities and interests; and (3) people tend to flourish in environments that are congruent with their dominant personality types. In this work, the authors have examined the validity of all three basic assumptions of Holland's theory. The two primary purposes of this current study are: (1) to examine more closely the gains and losses of students who are congruent or incongruent with their chosen academic environment with respect to the analogous sets of abilities and interests; and (2) to explore the possibility that students who enter academic environments not congruent with their dominant personality type incur various "costs" in relation to their peers who enter congruent academic environments.