Purpose: The transition from higher education to employment is a major life change for many college seniors (currently, the Generation Y cohort). The purpose of this paper is to enhance the understanding of Generation Y and to present new insights regarding Gen Y's retail career expectations, perceptions of retail careers, future psychological contract/entitlement perceptions of retail careers, and career exploration of the US retailing industry. Design/methodology/approach: Utilizing quantitative research methods via an on-line survey, the authors examined 193 Gen Y college seniors' retail career perceptions and expectations, and explored the influence these factors have on future psychological contract/entitlement perceptions of employer-employee obligations and retail career exploration from nine US universities. Findings: College seniors' pre-entry retail job expectations, perceptions of retail careers, and future psychological contract/entitlement perceptions of employee obligations were significant predictors of career exploration; college seniors' preconceived notions of retail careers, combined with what they feel they would owe their future employer, are instrumental in determining retail career exploration decisions. Research limitations/implications: Findings suggest directions for university faculty, academic advisors, and industry practitioners on facilitating college seniors' transitions from higher education to the world of work by suggesting recruitment strategies that can attract, retain and motivate Gen Y. Originality/value: The findings provide useful criteria for organizational development strategies to assist with the transition from higher education to the workforce and may also improve the success of recruiting Gen Y employees. In addition, the conceptualization of psychological contracts (i.e. entitlement perceptions) differentiates this study from prior psychological contract research. (Contains 4 tables and 3 figures.)