Using a case study, this paper explores the pedagogy and logistical best practices of leading short-term study trips to the indigenous highlands of Guatemala. The goals of community-engagement are to have students: 1) interact with people of different cultural, linguistic, political, and economic world views, expanding their range of diversity-training; and 2) think critically about poverty and human agency in a global context. Logistical considerations are a key component of the learning experience when markets suffer from asymmetric information and moral hazard. This paper contributes to the literature by highlighting the ways that planning, programming, and logistics need to be woven into sustainable approaches to community engagement. For this to be an ethical endeavor, local peoples should be involved with the development and execution of the program. A barrier to learning can be a perception by students that, given their comparative economic privilege, they are there to "help" poor families. Students learn from host families about a different and holistic worldview, and gain insights into business development and its barriers. After the trip, students have a new way of thinking about diversity, agency, and workable approaches to ethical and sustainable self-help business developments.