The media in Ireland paints a negative picture of people who have been to prison. People with convictions, regardless of what those convictions may be, are largely deemed untrustworthy and unemployable. A prison sentence in Ireland has the capability of literally ruining someone’s life and future. Irish prisons are mostly filled with males from working class backgrounds. It is no coincidence that most of the working class males within prisons have high literacy issues and low educational attainment (O’Donnell, et. al, 2008). The importance of educational attainment in order for the awareness of one’s situation, one’s employability and life chances and one’s overall freedom is undeniable. To ask the research question of what impacts early school leaving and imprisonment amongst males in Dublin, Ireland it would be deemed unreliable research if the topic was not explored with the direct aid of a group of males from Dublin who have experienced early school leaving and imprisonment in order to provide this arguably unique group with a voice and also to present the cause and effects to these and multiple linked social and personal issues experienced by the group for richness, reliability and validity throughout. The group of research participants who have contributed so much to this research have all been sourced in an education centre where they all frequent and engage with various levels of education. They also all receive and provide emotional, personal and academic support to the other learners who frequent the centre. The fact that each of the group have all experienced early school leaving and imprisonment and are now each involved in and identifying education as a means of staying out of prison really engulfs and breathes through this research. The exploration of what impacts early school leaving and imprisonment amongst males in Dublin, Ireland has unearthed a number of relevant social and personal issues that require significant consideration. Issues of early school leaving, identity, masculinity, emotional intelligence, rational choice theory and imprisonment are impacted by issues of power, oppression, structure, agency and social class. These issues have all been found to be the lived experience for the research participants and the issues have been linked and analysed through a theoretical lens with theorists such as Pierre Bourdieu (1984), Karl Marx (1844), Emile Durkheim (1833, 1933), Max Weber (1922), Erving Goffman (1959), Paolo Freire (1970), Raewyn Connell (1995, 2005), John Scott (2000) and many others to show the importance of identifying the lived experiences of the group of research participants.