This qualitative case study documented, described and analyzed the experiences of 51 students voluntarily enrolled in a Progressive Alternative Education Program (PAEP). The study explored participants' perceptions towards learning (social and academic) as they participated in the PAEP. A variety of data sources facilitated in depth exploration of the research questions, including a survey of the participants' perceptions of school and learning, recording extensive field notes during the various components of the PAEP, focus groups and individual interviews (these, and daily activities of PAEP were audio-taped and transcribed). The data was analyzed to uncover patterns in perceptions about learning and to document changes in these perceptions over the academic year. It is noteworthy that each participant, by the end of the study, indicated that their perception of themselves as learners and as active participants in learning had evolved. Four hypothesis were generated by this study: (1) Learners who perceive their academic courses as being pertinent to their personal goals are more likely to persist in the achievement of these goals, (2) When students explicitly connect classroom experiences and “real world” experiences, student motivation is enhanced and understanding is greatly aided. When these connections are unclear or disregarded, students may disengage from academic studies, (3) Students who are disengaged from academic studies may be re-engaged when participating in a community that they see as valid and valuable. Students who are engaged in academic studies may find deeper cognitive and motivational connections if they connect to an active and engaged community of learners, and (4) Giving opportunities to develop personal goals, self-efficacy, an internal locus of control, and resiliency requires allowing students to direct their own path, and, at times, to make mistakes. Further research is suggested regarding the following areas: examining long term affects of participation in secondary PAEP, empirical testing of the hypothesis of allowing students to direct their learning and to make mistakes, studies in comparison PAEP wherein students are mandated to attend, as well as studies in public school settings that take a progressive approach but serve all students in the community (as opposed to a select population).