There is a lack of empirical data on the experiences of people with mental illness (PMI) who transition from welfare to work, or how policy programs are designed to facilitate this outcome. We explore the factors that facilitate or hinder PMI from exiting disability income support programs in Ontario, Canada. Drawing on a grounded theory approach, we examine the process of exiting the Ontario Disability Support Program (ODSP). Data were collected from semi-structured interviews with current and former recipients with mental illness, service providers who support current and former recipients, and ministry staff. A metaphor for the work exit process emerged with four embedded themes: (a) picking yourself back up, (b) breaking the rules to get ahead, (c) stabilizing illness for employment success, and (d) displaying resiliency and resourcefulness for successful exits. The main finding is that system supports are not the determining factors in a successful transition. Rather, participants describe how recipients exit for employment by leveraging personal resources to successfully transition off income support benefits. A system redesign is needed to address the inherent tension between social and health programs if the policy intent is to promote successful welfare-to-work transitions for PMI.