There are many factors that influence students in their choice to take vocationally focussed or general technology subjects at secondary school. Equally, there are many factors that contribute to whether or not they succeed in their studies, and what value they place on the different types of knowledge and skills they learn. A student‟s choices cannot be separated from the social and environmental context in which the student acts. This study presents five case studies that explore the context and experiences of five, very different students of technology who have all recently graduated secondary school. Each case study brings together data from semi-structured interviews conducted with the student participant, one of their parents and their principal technology teacher at secondary school. They provide an insight into how each student perceived their technology education, what influenced them in choosing technology classes, what knowledge and skills they learnt, how that knowledge and skill has served them in their transition into the workforce or tertiary study, and what they perceive are the differences between vocational technology education and general technology education.