This study examined the associations between personality and protean and boundaryless career orientation and the mediating role of motivation orientation. In total, 273 Israeli students engaged in full-time employment completed questionnaires, which were used to assess the variables of interest. Structural equation modelling path analysis supported most of the expected hypotheses. The associations between personality and protean and boundaryless career orientation were partially mediated by motivation orientation. Learning goal orientation mediated two aspects of protean career orientation (self-directed and value driven), and one aspect of boundaryless career orientation (boundaryless mindset). Performance goal orientation exerted a negative mediatory effect on a second aspect of boundaryless career orientation (mobility preference). Overall, the results suggested that the Big Five traits, Extraversion and Conscientiousness, were associated with protean and boundaryless career orientation via learning goal orientation, and Neuroticism was associated with preference for organizational stability via performance goal orientation. Interestingly, Openness and Agreeableness were associated with protean and boundaryless career orientation via learning orientation and to preference for organizational stability via performance goal orientation.