The aim of this study is to investigate the occupational orientations and choices of young people in rural Crete, a society, which is in constant change as it finds itself caught between tradition and modernity. To achieve this, the study looks into two cases: the case of Anogia, a small mountainous cattle-raising village, and the case of Archanes, which is a farming village on a plain. Both communities are undergoing a process of change due to the influence exerted upon them through the frequent contacts with the ‘outside world’ and the diffusion of modernity in all areas of life. The study expects to shed light on how the young people of these villages experience the transition from tradition to modernity and how this transition influences their choice of occupation. More specifically, the aims of this study are to investigate: A. The occupational orientations and choice of occupation of the young people within the communities of Anogia and Archanes. B. The main contextual factors that contribute to the young people’s occupational orientations and choice of occupation in Anogia and Archanes. The overall approach is a qualitative inquiry consisting of two case studies. The empirical research took place in the field of the communities of Anogia and Archanes, and addresses 29 young people of the villages, so as to gather primary data through semistructured interviews. The age has been defined to be 16 to 25 years old. In order to arrive at the findings, data analysis derived from the Grounded Theory methodological approach was employed (Strauss, 1987). The main findings of the study show that the transitional process from school to work seems to be the most crucial issue for the young people under study, in the process of shaping their occupational orientations and choices. The attitude, either positive or negative, that each one has adopted towards school and education generally and the level of education constitutes the main tool that determines the limitations and the opportunities for job placement. In these small societies, the traditional roles have been overturned as regards the youth and their professional orientations. The majority of young people follow new practices in seeking employment. These characterise the following three types of youth: the stayers, the ambivalent and the leavers