Previous research has identified that students from disadvantaged backgrounds and those with low academic achievement experience the most difficulty in making the transition to work and further study (Saha & Sikora, 2011). Off-shore transfer of low-skilled jobs to developing countries has contributed to growing youth unemployment in many developed countries, forcing governments to pay closer attention to those student groups (Tomlinson, 2012). Australia has not escaped this phenomenon, with the number of jobless young people reaching 40 per cent of 15-19 year olds in some regions (Mission Australia, 2010). Governments at both state and federal level have sought to address this issue through policies designed to raise student aspirations and to increase knowledge about post-school options. Neither initiative will address student career choice capability, however, which is influenced both by students' educational experiences and their socio-educational background. This study aims to better understand associations between students' socio-educational backgrounds, their educational experiences, attitudes towards schooling, and level of career certainty. Students (N = 706) from 12 schools (7 government and 4 independent / girls-only, boys-only and co-educational) from both metropolitan and regional areas of NSW were invited to participate in an online survey examining student backgrounds, including: parent occupations; attitudes to school and to learning; and finally, student aspirations and related knowledge of required further education or employment. We found no significant differences in the proportions of students who were ‘uncertain' of their future career aspirations with respect to socio-educational background (as measured by the Australian government's Index of Socio-Educational Advantage). There were, however, significantly more students struggling with career decision making in particular regions of NSW. Those students were proportionally present in government and non-government schools and had some behavioral and attitudinal characteristics in common. Better understanding of the students' characteristics allowed the authors to provide recommendations for educational policy makers in their future reforms.