The two authors share learning gleaned from personal, classroom experiences in small schools--both cautions and assurances--for other educators who may be embarking on a similar path. We worked at two different small high school sites in the Denver Public Schools, an urban district with an ethnically diverse student population of 78,000. We present a multi-vocal analysis of participants in both sites to identify consequential experiences and perspectives from five stakeholder groups: teachers, students, parents, administrators, and partners/advisers. For each stakeholder group, we document roles, goals, responsibilities and activity patterns. We summarise a set of findings identifying the conditions for success in a small school project. (Contains 1 note and 2 tables.)