Occupational therapists have an established and important role in helping people work while living with an illness or a disability. Although workplace accommodations and rehabilitation efforts can extend paid work for workers with progressive health conditions, the reality is that these populations often cease work earlier in the life trajectory than expected. Evidence suggests that transitioning out of paid work is difficult for people with disabilities. For example, factors such as poor health, low income, and involuntary retirement put people with multiple sclerosis at risk for poor adjustment. Given society’s emphasis on paid work, the transition to unpaid work has received little attention. Occupational therapy practitioners are well positioned to contribute to enhancing the quality of life of people in work-cessation transitions who are not of traditional retirement age.