This paper focuses on how British colonial institutions adversely affected the adolescent characters in James Joyce’s Dubliners and A Portrait of the Artist as a Young Man. The adolescent crisis of identity found in Joyce’s works starts to take shape when the characters reach a pivotal point in their lives. The characters are forced to make a choice: conform to societal expectations or follow their individual instincts and risk social alienation. In addition, the characters that are undergoing the crisis of identity in Joyce’s writing are being influenced by society to make decisions that are diametrically opposed to what they truly want. In the first two examples from Dubliners, the protagonists give in to societal pressures and do what is expected of them. The third example, Stephen Dedalus in Portrait, despite enormous pressure from society to conform, chooses his own path of non-conformity. In all cases, the crisis of identity proves to be an extremely psychologically intense experience for the character regardless of whether he/she chooses to conform or not to conform. In exploring this important transition into adulthood, Joyce shows the adolescent characters as they face the most critical decisions of their young lives and tempers them for adulthood.