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The active exploration of career goals is an important task that prepares students for successful school and work. Studies indicated that students who hold clear career goals are more likely to develop a stronger interest in their chosen field of study and make more sensible career-related decisions. This study examined clarity of career goals and positive outcomes and how this relationship may be moderated by proactive engagement. Based on a study of 16-year old adolescents in Singapore, the findings indicated that 1) clarity of career goals contributed significantly to students’ confidence in the future, and 2) engagement in proactive career behaviors acts as a psychosocial buffer against low career clarity in the attainment of positive student outcomes.