Since the beginning of the 20th century, researchers have been writing about the importance of expressing by art during the early childhood for cognitive and mental development. This article examines daily art activity after school entry and its effects on the transition from kindergarten into school. It is based on a research project conducted by an international and interdisciplinary research team. The researchers come from the fields of art education as well as from pedagogy and didactics of primary level from two different countries, Israel and Germany. The use of sketchbooks as a private visual diary gives the children an additional voice and provides them with opportunities to play, imagine and decide how to integrate formal knowledge into the familiar visual language of art. Based on our findings, we discuss whether the sketchbooks activity can transform the class into a social learning community and if they cushion the transition into school.