In this paper, we examine the class structure and kind of guidance and support teachers must provide to their students to create new meanings and values through the generative production of artworks in the subject of “”Representation in Pictures” for 6th grade elementary school students. This study shows that students can create new images beyond the generative exploration of unknown expressive activities by 1) responding flexibly to the changes produced by the relationship with materials and the act of expression and 2) using even deviations from the expected image, accidental discoveries, and failures as triggers to begin the search for a new image. Through the discovery or accidental discovery of an image as well as the failure of an image being a trigger for the search for a new image to begin, it is possible to create a new image beyond the generative exploration of unknown expressive activities. Simultaneously, it was found that it is important for teachers to establish flexible learning settings and explore together with children as an open teacher through 'individualized guidance’ from the viewpoint of the process of “Formative Play” activities and reflective appreciation activities.