Technological and vocational education has become an important issue while lifelong learning is widely accepted. However, should it concentrate on preparing students for specific jobs or should it be more focused on broader career development, including lifelong learning, employability, and cognitive skills? This paper explores these questions and examines how technological and vocational education programs can best prepare students to meet the demands of the current and future workplace. This paper concludes that successful career development in technological and vocational education requires educators who are willing to take risks, to forego the need for control and to allow students to pursue their own learning, which implies asking their own questions and seeking their own answers.