This chapter discusses a number of perspectives on the transition to work, including a review of the increasingly important notion of self-employment. It begins by outlining recent discussions around the notion of career. It then reviews a selection of dominant theories relating to career decision-making and development, using these to improve understanding of transition from education to work in tourism and hospitality. It discusses attitudes towards work among youth as well as early work and placement experiences and how these facilitate or hinder the transition into tourism employment. The chapter closes by looking at the role of SMEs and graduate entrepreneurship as relatively unexplored but important destinations for graduate (self ) employment.