This paper examines the behavioral issues associated with homelessness and marginal lifestyles. It describes classroom techniques that may be used to develop self-directed learning readiness as a tool for mitigating the psychological problems associated with the causes and outcomes of marginal living and homelessness. Discussed first are 26 issues associated with homelessness/marginal lifestyles, including the following: nonsupportive/no family networks; learned helplessness; inability to admit needing help; sense of social valuelessness; social isolation; fear of failure; proneness to victimization; lack of education; stress; alcoholism; unemployment; and lack of physical space. Next, the differences between normal, situational, secondary, and primary depression are explained along with recognized cognitive treatments for depression. Goal-setting activities and group activities that are based on the techniques underlying the cognitive treatment of depression and that are designed to facilitate development of self-directed learning readiness are outlined and discussed within the context of social exchange theory and loss and attachment theory. In the paper's conclusion, some successful applications of the approach of using self-directed learning as a way of mitigating the psychosocial problems associated with marginal living and/or homelessness are highlighted. (MN)