From their nascent beginnings during World War II to their good governance and capacity building focus under the Post-Washington Consensus of the early 21st century, international development activities have encompassed a particular world view. This world view, founded on Western historical materialism and a normative perspective, rationalizes “the project” as the predominate form of development assistance and the “expert” or “volunteer” as its agent. Yet this approach to development, although at times successful, has often proved to be unsustainable in the absence of international financing and expertise. Still, there is an alternative approach available when one recognizes that what the vast majority of people want is security for themselves, their families, and their lifestyles.1 From this approach, the focus of development is shifted away from what people do not have (be it material comforts, infrastructure, or good governance) and sets it on the critical roles culture, individual growth, and informal association have in community development. In this approach, human agency at the interpersonal level becomes critical in the diffusion of social, political, economic, and technological innovation and, accordingly, the decisive factor in poverty reduction. That is to say, development that can address poverty must come from within the social classes that experience it. To explore how the international development community can act on this alternative approach, this thesis provides a review of the theory, practice, and consequences of international development to the present day and, from that lead, builds a theoretical argument for the individual creative sojourner as a primary messenger of development. In addition, it presents an exploratory case study of creative sojourners in Timor-Leste and, from their ideas and insights, proposes policy considerations for an overseas apprenticeship program that would support the efforts of trades people, agriculturalists, and small entrepreneurs in improving their lives and, in the process, renewing their societies.