Today's boundary-less and knowledge-based economy with its focus on learning organization delivers a contradictory message to employees in managing their careers. On the one hand, contemporary organizations expect and demand that employees adopt a lifelong learning approach, be global-oriented, successfully manage the dynamics of diversity in the work and marketplace, work in self-directed teams, develop a feel for and rapid response to fast changing customer expectations and so on. On the other hand, organizations are silent on the question of who is going to bear the enormous cost of ongoing technical and behavioral training that the employees need to successfully manage in a global village. While today individuals accept the fact that they can no more expect the organizations to provide them lifelong, full-time and stable careers, they would certainly prefer not to work for organizations that adopt the "help us but help yourself" attitude to career management. This paper discusses the implications of this paradox on the career management process at the organizational level and reviews best practice scenarios.