Adolescents continue to be at risk of disengaging from formal education, particularly in the transition year from primary to secondary schooling. This is a critical time in their education journey and can affect their ongoing academic performances. This paper reflects on the initial findings of a project to gauge students' levels of engagement in the first year of secondary school (12-13 years of age). The project was undertaken with students in 4 schools in two Australian states, located in low socio economic areas. Approximately 80 students from the 4 schools were selected to participate in an intervention project with specific targeted activities that aimed to increase levels of engagement in schooling to eventually aid them to aspire to desired career choices. A mixed methods research approach enabled us to capture, analyse and report on the participating students' perceptions in terms of their attitudes towards schooling, their academic performance, and selected aspects of school life. We also interviewed their parents and teachers about these topics. The results indicated that there were some changes in attitudes towards schooling for some individuals, but generally the majority of student engagement levels remained static or tended to be negative. This remains a cause of concern for educators who are trying to find ways to encourage students to be more engaged with formal education that supports their career aspirations.