This multiple case study illuminates the individual change trajectories of four homeless men with mental illnesses who participated in a manualized life skills intervention to improve housing retention. Readiness-to-change, life skills knowledge and trauma symptoms were measured at baseline, post-intervention and at 3-6 months follow-up. Cluster analysis identified two patterns of readiness-to-change: engaged and pre-engaged. Change is non-linear and baseline readiness is not necessary to benefit from the intervention. Examining individuals' lives in context illuminated the change process and demonstrated that varied patterns can lead to successful outcomes for housing stability and community reintegration.