This study examined a model in which the anxious and the avoidant forms of insecure attachment were related to career indecision through the mediation of self-criticism. One hundred seventy-three college students completed questionnaires measuring anxious and avoidant dimensions of insecure attachment, self-criticism, and career indecision. Path analysis indicated that avoidant attachment was indirectly related to career indecision through the full mediation of self-criticism and that the linkage between anxious attachment and career indecision was partially mediated by self-criticism. These findings advance the understanding of how internalized relationships with significant others may impact career planning and development, suggesting distinct mechanisms by which the anxious and the avoidant forms of insecure attachment may exacerbate career decision making. In addition, the findings highlight the centrality of self-criticism in the process of career decision making. Implications for the career decision-making process and career planning are suggested, and recommendations for career counseling interventions are presented.