The purpose of this study was to examine a theoretically-based model in which insecure attachment is related to career indecision through the mediation of negative emotions. Two hundred college students completed questionnaires measuring anxious and avoidant dimensions of insecure attachment, negative emotions (trait and career-choice anxiety, trait and career-choice pessimism), and career indecision. Path analysis indicated that anxious attachment was indirectly related to career indecision through a full mediation of career-choice anxiety and career-choice pessimism (but not through the trait emotions). Avoidant attachment was neither related to the negative emotions nor to career indecision. These findings contribute to the understanding of the linkage between internalized relationships with significant others and career planning and development, and highlight the important role that career-choice-related emotions play in the process of career decision making. In light of the findings, implications and recommendations regarding career development, career counseling interventions, and preventive measures aimed at reducing career indecision are presented. (Contains 2 tables.)