In contemporary education, there is increasing interest in the potential of mindfulness-based training to improve mental health, behavior, and school performance, as part of fostering contemplative pedagogy that can positively impact the lives of young children. However, practice-based knowledge is lacking about how to implement mindfulness-based training effectively at schools. Thus, the key question motivating our study was how we can create school-based educational programs that cultivate mindfulness in young people. The study, a retrospective, qualitative analysis of 188 letters written by 112 elementary students who participated in a classroom-based mindfulness-based training curriculum in the mid-1990s, provided an unique opportunity for gaining important insights into ways in which the students viewed the mindfulness-based training curriculum, themselves, and each other when undertaking that training. Applying the principles of qualitative analysis, each letter was coded, and codes were constantly compared, and from this five thematic categories emerged about central aspects of the process and implementation of that mindfulness-based training. They were: (1) Importance of a sense of place; (2) We are more of a community; (3) Actively taking it on; (4) How I relate to others; and (5) Getting in touch with the inner self. A key finding is that the mindfulness-based training program was a sustained process facilitating the cultivation of a range of students’ skillsets, and not simply reduced to attentional techniques acquired in a finite time slot in an otherwise unchanging classroom. This finding has important implications for the way mindfulness-based training is conceptualized and implemented in contemporary school settings.