This study explored the predictors of financial self-sufficiency among Social Security beneficiaries with psychiatric disabilities. The study was conducted with individuals who were either past or current disability beneficiaries and who had sustained competitive employment as evidenced by their involvement in a longitudinal investigation on sustained employment among persons with serious mental illnesses. We conducted an exploratory cross-sectional study employing a survey methodology to determine what factors were associated with participants' capacity to leave the Social Security disability rolls due to gainful employment. We used a stepwise approach to data analysis to explore the association of demographic, clinical, vocational and motivational factors with financial self-sufficiency. Results suggested that individuals with higher occupational status, higher levels of proactive coping and without medical comorbidities were more likely to terminate Social Security disability benefits and achieve financial self-sufficiency due to gainful employment. Study findings can inform the development of innovative interventions targeting these malleable predictors associated with financial self-sufficiency among persons with psychiatric disabilities.