During the 2008-2009 school year, faculty members at New Fairfield (CT) Middle School examined relevance and student engagement in relation to student achievement. Subtle clues indicated that students were not fully engaged in their learning: many students did not relate their classroom experiences to their personal reality or to their vision of their own future. As part of the strategy to examine student performance and attitudes toward learning, the administrators and faculty members drew upon the work of William Damon. Damon (2008) concluded that contemporary youth fall into one of four groups: the purposeful, the dabblers, the dreamers, and the disengaged. In staff meetings, teachers discussed what students in each of Damon's groups might look like and perform like in a classroom setting. Using the Connecticut State Department of Education--Connecticut Career Pathways: Seasons of Change and Transition, the staff and faculty at New Fairfield were able to help their students be fully engaged in their learning and find meaning in what they are doing.