This study examined the relationships among courage, strategies of coping with career indecision, and future orientation in a sample of high school students. A total of 460 Greek adolescents from provincial cities participated in the study. The results indicated that courage indirectly predicted future orientation through productive coping strategies. The main conclusion refers to the fact that specific interventions could promote productive coping strategies and courage, which in turn, may foster the future orientation of adolescents to construct multiple positive occupational pathways, coping with various career and life decisions and, overall, orient themselves positively toward the future.