This paper reports pilot data from an instrument devised as part of a large ARC funded project that aims, among other things, to investigate factors that influence the decisions of students in rural and/or disadvantaged areas to continue their schooling beyond Year 10. One section of the pilot student questionnaire comprised 42 items designed to reflect dimensions believed to influence these decisions. Participants responded on 5-point Likert scales indicating the extent of their agreement from Strongly Disagree to Strongly Agree with each of the items. We were interested in the extent to which the data supported the theoretical structure that underpinned the structure of the questionnaire and in testing the appropriateness of the language used. The large scale data collection will survey students from Years 5 to 11 with as few adaptations for differences in literacy levels across that range as possible. To this end, the pilot questionnaire was administered to Year 5 (n = 44) and Year 9/10 students (n = 50) with identical wording for both grade levels. A factor analysis of the complete data set (n = 94) provided initial evidence that being happy at school; having family support to continue with education, and appropriate curriculum options and extra-curricular activities, perceiving oneself as a high achiever both in general and in relation to mathematics, having teacher and peer support to continue, being positive about English, planning to be an apprentice, and having a job type in mind are dimensions worthy of further exploration in the larger study.