In this dissertation I trace the various forms of young men and women 'growing away' from society in Irish Bildungsroman and how this pattern of thwarted development reflects on Ireland's decolonization in the twentieth century. Whereas traditional Bildungsroman features the socialization of the protagonist who not only grows up but more importantly grows into the society, the persistence of Irish writers' representations of failed socialization should be understood as protests against the problems of the post-independence Irish state in its prolonged struggle of decolonization. In Chapter One I discuss James Joyce's A Portrait of the Artist as a Young Man as the precursor of post-independence Irish Bildungsroman, which not only sets up the pattern of growing away from Irish society but also designates 'home, fatherland, and church' as the problems confronting Irish youth. Chapter Two begins with a Gramscian analysis of the Irish 'passive revolution,' followed by discussions of Sean O'Faolain's Bird Alone and Kate O'Brien's Mary Lavelle to exemplify how the lack of change in the Free State is excavated and accounted for through the novelists' engagement with its past. Chapter Three deals with Edna O'Brien's The Country Girls Trilogy and the excessive obsession with the family, which makes it impossible for the individual to seek self-fulfillment in roles other than the familial. In Chapter Four I use Patrick McCabe's The Butcher Boy and Roddy Doyle's A Star Called Henry to show how novels of thwarted developments in the 1990s actually display a new confidence in exposing the failures of the state. The difficulty shared by protagonists in Irish Bildungsroman lies in that they strive to find their own places in the new state which is itself in the same predicament of self-definition, a postcolonial nation trying to become a normalized modern state after the end of colonialism. I argue that the pattern of stunted development, of protagonists constantly growing up not into but away from Irish society, is the sign of the individual's struggle with the postcolonial Irish state that is also struggling to be decolonized and to become modern.