In Japan, the number of workers with depressive symptoms has increased recently, and long working hours are considered one of the main contributing factors. Currently, the number of workers engaging in discretionary work is small but is expected to increase, as a diverse method of employment is believed to contribute to workers ' well-being. However, the factors related to discretionary workers ' depressive symptoms are unclear. This study aimed to identify the factors associated with depressive symptoms in discretionary workers . The subjects were 240 male discretionary workers in a Japanese insurance company. A cross-sectional study was performed using a questionnaire that includes demographic characteristics, living and working conditions, work-related and non-work-related stressful events, and the Center for Epidemiologic Studies Depression Scale (CES-D). Depressive symptoms were assessed as more than 16 points on the CES-D. Multiple logistic regression models were employed to estimate odd ratios (OR) with 95% confidence intervals (95% CI) of depressive symptoms in relation to possible factors. Thirty-six subjects (%) showed depressive symptoms. The depressive symptoms were significantly related to age (p = ), presence of child(ren) (p = ), and length of employment (p = ), but unrelated to working hours. Subjects who reported "financial matters" (OR = , 95% CI = -) and "own event" such as divorce or illness (OR = , 95% CI = -) were more likely to show depressive symptoms. In conclusion, mental health measures for discretionary workers should focus on addressing financial difficulties and consultations and assistance in personal health and family issues.