This study examined the role of work volition in the relation between college students’ health and several short-term career outcome variables. The responses of 393 students to an online survey revealed that the number of the last 30 days that were deemed unhealthy was significantly related to work volition, and work volition was associated with major satisfaction, leadership aspirations, educational persistence intentions, and real versus ideal career aspiration discrepancy. Path analysis results were consistent with a model specifying work volition as a mediator of the associations between unhealthy days and the career variables. It therefore appears lower work volition may be a risk factor for students with health-related challenges. When conducting career assessment and counseling, career counselors and other providers should consider the perceived career-choice constraints that college students with chronic illnesses and general symptomatology perceive. Limitations and future research directions are discussed.