This study sought to explore adolescent students' self-identity and educational identity, and to understand if these identities influenced students' educational decision-making. Drawing mainly on the theoretical work of Bronfenbrenner (1977), and to a less extent that of Rogoff (1998), Bourdieu (1991) and Teese (2007), this study investigated the notion that the students' socio-economic contexts help shape the students' participation choices and the development of their school identity. Specifically, the study considered if students' school, home and community experiences could be mapped using an alternative assessment procedure to written surveys, instead involving students' use of icons (pictures). The collage of pictures selected by the students is identified in this research as an 'identitygram'. The notion is that the pictures are, in part, representing the identity of the student. The target cohort was Tasmanian high school students transitioning from secondary school setting (Years 7 to 10) to a separate senior school campus Years 11 to 12). The age of the students in Year 10 clusters around 14 to 15 years of age. Tasmanian has one of the lowest rates of Year 12 completion rates across Australia. The causes of this low retention are reported to be linked both to higher levels of welfare dependency across the state and to lower student aspirations to transition to post-secondary education after Year 12. How to enhance the Year 12 retention rates and advance students' post Year 12 aspirations are core concerns of this research. This research is in two parts. Firstly, the pilot study involved the development and trialling of a set of icons that related to students' schooling, lives and aspirations. The participants were eight Year 10 students (5 male and 3 female) who attended a non-government urban high school. On each data collection occasion each participant was provided with a full 'kit' of 80 icons (pictures) developed by the researcher to select from, cut out and apply to paper to create each visual identity collage. Once finished, each collage became an identitygram. Each of the identitygram collages was coded separately for data analysis using NVivo (2016) software programming. Using a second cohort of Year 10 students, the second study further tested whether the icons changed after a brief orientation to Year 11 and 12 program of activities. The participants were 14, Year 10 students (7 males and 7 females) attending government high schools. The four research questions that guided the study were: 1 Is the identitygram procedure a suitable method to investigate students' self-identity? 2 Does school disadvantage influence students' depictions of their self-identity, as shown in their identitygrams? 3 What are the concerns of teachers for their students from disadvantaged communities as the students transition into Years 11and 12? 4 Does a brief Year 11 and 12 orientation course enhance Year 10 students' depictions of their self-identity? The evidence is that an 'identitygram' (picture collage) provided the researcher with an investigative tool through which to explore students' aspirations and fears using a non-threating medium. The findings supported the notion that the use of pictures (icons) produced a stable self-identity profile. It encouraged Year 10 adolescent students to talk about themselves in an interview setting that enabled the students to self-reflect. The findings also denoted that a brief Year 11 and 12 orientation course did bring about some changes in the students' icon complexity. This change was more in the selection of icons that related to the students' aspirations for future education. Data from students from more disadvantaged settings were associated with fewer education related icons when developing their identitygram, compared to their peers from higher socio-economic locations. This lends support to the theory that the social context influences an individual's self-identity. The teacher interview data noted that the students from disadvantaged communities typically lacked confidence about their future aspirations and had limited understanding of educational opportunities. The teachers recognised that in the Tasmanian context shifting from a Year 7-10 campus into a senior school Years 11 and 12 was problematic and that preparing students for that transition could be enhanced. The critical finding is an identitygram methodology provides educators and others with a useful focussing tool when seeking to better understand and explore youth self-identity.