The aim of this chapter is to reinterpret SSM from the “actuality” point of view. I will do this by drawing on the experiences of two SSM courses in action: one with Japanese people (Course I) and one with Japanese and Western people (Course II). In Sect. 6.2, I will examine the SSM process stage by stage in order to understand the Japanese way of using it from the “actuality” perspective. This is a key step in my reinterpretation of SSM as a new Japanese-style “Contextualised SSM (C-SSM)”. In this section, I focus on the basic philosophy of SSM as embodied in the methodology. I will explain SSM as a problem solving methodology in Chap. 7 . In Sect. 6.3, I will demonstrate the value of C-SSM as a methodology, based on Weizsäcker’s “Gestaltkreis” (see Chap. 5 ), to bridge between “actuality” and “reality”. Every basic concept of SSM will be rethought from C-SSM’s “actuality” point of view. Finally, in Sect. 6.3.4, I will examine Tsouvalis and Checkland’s (Systems Research and Behavioral Science 13, 1996; Systems Research and Behavioral Science 14, 1997) reinterpretation of SSM, which is, in a sense, close to C-SSM.