Pathways to academic and behavioral discouragement in youth are fostered by adult thinking, feeling, perception, and behavior that contribute to five environments that tend to evolve in succession as adults respond to perceived "problem" behaviors and academic underachievement by children and youth. These five environments are characterized by uncertainty, raised concern, tension, overt tension, and unhealthy conflict. This article describes the various patterns of adult thinking, feeling, perception, and behavior that contribute to the environments that cultivate discouragement in children and youth. Under the influence of these environments of pathways to discouragement, there is an escalating "disconnect" among the adults who are involved with the youth; and the problem solving is pervaded by discouragement, anger, and punitive consequences. Understanding the negative trajectory, however, provides insight into how the pathways to discouragement can become pathways to courage. Pathways to courage lead to environments of belonging, mastery, independence, and generosity. To create these environments of courage in the midst of problems that must be solved, adult efforts and attitudes focus on helping children and youth feel a sense of attachment (belonging), competence (mastery), power (independence), and worth (generosity). This article explains how adult thinking, feeling, perception, and behavior in the course of addressing academic and behavioral problems can lead from uncertainty and raised concern to environments of creative tension, experimentation, and constructive coping. 2 tables and 6 references