The imbalance of demand for and supply of qualified seafarers has always been a feature of the shipping industry with the shortage of skilled personnel having been the main concern for many years. The industry, together with other stakeholders such as maritime education and training institutions, has addressed the issue in various ways. Retention has been identified as one of the strategies to maintain a sustainable seafarer workforce for the shipping industry. This strategy was derived from the fact that the length of active seafaring career has been reduced in the last few decades and that efforts in increasing intakes have their limitations if recruited and trained personnel leave the industry within a short period after they start their seafaring career. Retention is also seen as a more cost effective means to address the shortage problem compared with the substantial resources required for the recruiting, educating, and training of prospective seafarers. The development of retention strategies requires a thorough understanding of the movement of the workforce and the reasons behind such movement. This chapter discusses how career pathways may play important roles in facilitating seafarer retention and maintaining a dynamic and sustainable workforce for the shipping industry. Due to the international nature of the industry and the high mobility of its workforce, conventional employee retention strategies need to be modified and applied at both organisational and industry levels.