This project examines C.L.R. James, V.S. Naipaul, and George Lamming's appropriation of the European Bildungsroman, a novel depicting the maturation of the hero prompted by his harmonious dialectical relationship with the social realm (Bildung). I contend that James, Naipaul, and Lamming use the Bildungsroman genre to critique colonialism's effects on its subjects, particularly its male subjects who attend colonial schools that present them with disconcerting curricula and gender ideologies that hinder their intellectual and social development. Disingenuously cloaked in paternalistic rhetoric promising the advancement of "uncivilized" peoples, colonialism, these novels show, actually impedes the development of its subjects. Central to these writers' critiques is the use of houses, space, and land. Although place functions differently in Minty Alley, A House for Mr. Biswas, and In the Castle of My Skin, the novels under consideration here, the corresponding relationship between a mature, autonomous self and a home of one's own is made evident in each. Tragically, the men in these novels are never able to find communities in which they cease to feel out of place, nor are they ever able to find secure domestic spaces. Because the discourse of home so closely parallels the discourse of Bildung, I contend that the protagonists' inability to find stable housing suggests the inaccessibility of Bildung in a colonized space. Further, I assert that this literal homelessness is symbolic of the educated male's cultural exile; he is unable to find a location where he can live in dialectical harmony with any community, which is the ideal aim of Bildung. Leaving the Caribbean proves to be the colonized male's only strategy for pursuing Bildung; thus, these novels suggest that while Bildung is impossible in the Caribbean, it is not impossible for the Caribbean subject.