This study investigates the factors likely to affect an individual’s decision to enter farming after and/or while participating in an off-farm employment activity. Additionally, an ordered multivariate regression procedure was used to analyze the degree of importance of selected motivating reasons that were drivers of individuals’ decision to enter farming. Results indicate that individuals with lower education, children in the household, and older family members were more likely to have entered farming as an occupation. Findings further suggest that federal policies in the form of farm program payments may provide retired nonfarm workers incentives to enter farming in later life.