Since the fall of the Brazilian military dictatorship in 1984, a number of structural and ideological changes associated with demilitarization and democracy have changed the face of psychiatric theory and practice. Around the country, pockets of innovative, politically sensitive and Marxist-inspired community-based forms of “psi” practice are developing. This emergent psi movement is making a range of positive contributions to the lives of average citizens, including those of poor disenfranchized youth. This paper, however, explores one particular dimension of the work of psi practitioners that has proven antithetical to the psi community's current politicized community-based aims. Based on qualitative and quantitative longitudinal ethnographic fieldwork with therapists and young men in Pelotas, this paper analyzes how certain kinds of psi interventions being carried out in schools for a subset of lower-class young men during their early teen years are encouraging some youth to seek military training as a life option. Although these young men initially had quite captivating, engaged and politicized—if also conflicting—interactions with therapists, their eventual disillusionment with their therapeutic and scholastic experiences resulted in high levels of social alienation and de-politicization. In these young men's search for what can best be described as formulaic solutions to troubling psychological experiences associated with a tumultuous institutionalized transition to adulthood, military training came to represent a form of self-cultivation and self-therapy. Several youth also hoped military training would enable them to actively disengage with local political processes and find shelter from troubling social inequities and injustice. The paper ends by reviewing the implications of these results for the future of psi knowledge and practice in Brazil.