Career indecisiveness involves more pervasive, severe, and chronic difficulties in making career decisions and focuses on deeper personality roots as well as cognitive origin. The purpose of this study was to examine the associations between career indecisiveness on one hand and self-esteem, personal indecisiveness, and five-factor personality characteristics on the other. As hypothesized, the career indecisiveness was higher in 545 Turkish high school students who had not yet decided on a profession than that of decided individuals. Also, the results showed that emotional and personality-related career decision-making difficulties are positively related to self-esteem, exploratory and impetuous indecisiveness, and neuroticism, while being negatively related to extroversion and conscientiousness. In addition, female experienced more career indecisiveness. Based on the result of the multiple regression analysis, exploratory indecisiveness was the most significant contributory factor to career indecisiveness for female and male.