This study explored the relationship between self-development as evidenced in the domain of narcissism and the process of vocational development as evidenced in career values, planning, and decisiveness/self-efficacy. It was suggested that this relationship would be impacted by family birth order and gender. Heinz Kohut's theory of self-psychology was utilized to understand narcissism from both an adaptive and maladaptive, developmental perspective. A review of narcissism and self-development theories was included to provide a comparative and comprehensive approach. Literature indicated that the development of narcissism was influenced by birth order and gender. Additionally, a review of the literature suggested a connection between Kohut's theory of the self and narcissism and aspects of the career development process, such as planning, decision-making, and occupational values. The sample consisted of 346 undergraduate students. Structural Equation Modeling was performed to test causal hypotheses. The major findings of the current study were that superiority (a measure of grandiosity) predicts altruistic career values and career decisiveness. Superiority is a slightly better predictor of altruistic career values than decisiveness. Additionally, goal instability (idealizing) predicts altruistic career values and career decisiveness. Goal instability had a predictive value that was nearly three times stronger for decisiveness. The results indicated that birth order and gender were not moderator variables in examining the relationship between goal instability and superiority. This study provided insight into the relationship between narcissism and the vocational/career development processes. These relationships may be important for career counselors and other related professionals. These findings may encourage counselors to assess and understand a client's narcissistic tendencies and individual representations when assisting in the career development process. A client's values regarding career options, along with his/her associated self-efficacy and ability to make important decisions, appear to be factors to consider when counseling an individual through vocational/career development. Limitations of the study were addressed and directions for further research discussed.