This longitudinal study examined differences in intervention outcomes based on readiness-to-change cluster profiles among 73 adults with a mental illness at risk for homelessness participating in a manualized life skills intervention. Intervention topics included money management, food management, safe community participation, and room- and self-care. Life skill knowledge and readiness-to-change, measured using the University of Rhode Island Change Assessment, was examined at baseline, post-intervention, and 3-6 months later. Two scoring patterns emerged for readiness-to-change at each time point: Pre-Engaged and Engaged. Participants who were Engaged at the time of assessment scored significantly better than Pre-Engaged on post-intervention life skill testing, however group identification changed over time. Baseline readiness-to-change did not predict future performance or attrition, and therefore may not provide accurate indication of client investment for future learning or participation. Further investigation is needed to determine what factors contribute to Engaged membership.