This study analyses the role of design procedures under Cultural Historical Activity Theory (CHAT) in the system of the activity and in the educator/designer’s professional and personal skills. Our effort has come as metacognitive outcome of a research that took place at a Contemporary Art Museum and in a classroom for students (11 years old). The purpose of the initial research was to highlight how an educational program under CHAT in a Contemporary Art Museum with the Life Cycle of Materials, as its Object, could affect students’ sustainable literacy, motives and relationships. As a metacognitive process the educator/researcher, who was simultaneously the designer, also studied the transformational processes of all Subjects of the activity system as well as her professional and personal transformations as an internal study for self-literacy. This paper describes trajectories of strategies, interactions, and expansions to the activity system, and puts forward for discussion the use of theoretical tools and epistemological principles of expansive learning for metacognitive analysis. Practical engagements with the theoretical framework of CHAT, came out as an important factor in the development of transformative agency and self-literacy at a professional level.