This paper provides initial evidence of the effectiveness of an educational program in a Tasmanian regional community that has experienced ongoing industrial restructuring. In response to these changes, community and civic leaders adopted a multifaceted strategic plan to address employment needs and opportunities. Part of this plan involved targeting school children to help them explore a broader range of educational and career options. The program, Aspire High, involves Year 5 children visiting workplaces, the local Year 11 and 12 college, the local technical college, and a local university campus. This paper reports results from student interviews and surveys. While it is difficult to attribute changes in students’ attitudes and aspirations solely to <i>Aspire High</i>, it is evident that they were enthusiastic about the program. Secondary findings showed that students become less positive towards school by Year 8, and that boys are less likely to be positive towards school and more likely to choose a traditionally gendered occupation.