There are numerous career development theories and models. Because of the complexity and fluidity of contemporary career development there is need for modern models to assist individuals to navigate career paths with purpose and clarity. The Career Sailboat Model (CSM) was created to enhance the process of career decision-making which emerges within four interactive dimensions - individual, social, political-legal-economical and chance. CSM uses a metaphorical presentation and focuses on the determination of career goals by promoting the process of self-discovery. This process is facilitated by overlaying a structure which guides both the discovery of self and the evaluation of career opportunities and options. This process utilises all of the career counselling processes including self-knowledge, recognition of educational/professional possibilities and decision/career planning. The model is founded on the idea that one’s passage to a career is a sailing journey from origin to destination. While the tentative selection of a career can be an intimidating process, the process of planning and navigating a journey can be much less so. This model was inspired by the work of many others and many earlier theories. Accordingly, and consistent with constructivist views, the CSM is engaged in helping individuals to compose their own stories and to determine their own destination ports. The model easily permits the use of informal/qualitative assessment instruments by guidance counsellors, for example, use of games, self-report inventories, card sorts. The CSM also allows for great flexibility and adaptation to a wide variety of cultural/social realities and to political-legal-economical dimensions.