The paper which follows was born out of the need to reflect on the experience gained during a teaching assignment mobility realized within the framework of an Erasmus+ KA1 project and targeting the core principles of the Democratic School. Drawing from the theoretical background of Sociocracy which calls for a different view of schooling and aims at reinventing learning and teaching, the paper aspires to communicate the observations made and recorded in a journal, feelings sparked and thoughts evoked while spending a period of twenty-one days as a member of a diverse yet enthusiastic school community in Deurne, North Brabant, the Netherlands. The major goal is to initiate a personal quest of the meaning and means of education through the juxtaposition of two approaches, a traditional and an alternative one. The discussion touches upon many pedagogical issues like the inner drive to learn and how this is accomplished in both contexts. The pursuit and development of meaningful changes in the school environment which will be powered by the notion of play, freedom to learn and democratic co-existence constitute the proposal of this work.