Nowadays, in the era of flexible and precarious employment, the concept of a ‘career for life’ in one organisation appears to be redundant, as most employees in the global labour market do not have permanent employment (ILO, World employment and social outlook: the changing nature of jobs. Geneva: International Labour Office, 2015). This chapter focuses on the shipping industry as an example of a global industry that employs over a million seafarers (BIMCO, Manpower 2005 update: the worldwide demand for and supply of seafarers. Warwick: Warwick Institute for Employment Research, 2015) as their main labour force in what could termed flexible employment. The chapter explores the idea of having a ‘career’ within the precarious shipping industry by focusing on the reasons for joining, staying, and leaving a seafaring occupation. The chapter is based on existing literature, and on recent data that was collected as part of a study on seafarers’ career development.