The history of the human-centered system movement (Gill in AI Soc 10(2), 1996) tells us that information technology (referred to as IT below) has come to dominate our life-world or societal functions. Since from 1990s, its streaming influence could be called ‘abnormal.’ Since entering the twenty-first century, the IT system has been on automatic acceleration and has been spreading more and more rapidly to many facets of our lives. In many sectors, this ubiquitous streaming of IT is seen to be central to societal development, and in a Japanese sense, IT could be seen as a resource to realizing technologically a mature society. This trend of IT seems to be unstoppable. In this sense, IT dominance can be regarded as abnormal to the point that IT-centered information systems (referred to as IS below) fall far short of the deep appreciation of the complex and diverse life needs of people and societies, and this leads to the implementation of IT/IS from technological perspective, with a belief that everything, which we can do could be and should be, done now by IT/IS. However, as IT/IS have become to be embedded in many facets of societies and are influencing over our everyday life, we need to examine them not from the point of ‘capability’ but ‘allowability,’ in other words, not from the perspective of technology (cognition), but from the prospective of intuition and feeling of actual life (action). We term reality as seen in the narrow sense of cognition and actuality as seen in terms of action (Uchiyama in Theory and practice of actuality, Daito Bunka University, Tokyo, 2003). We draw a distinction between the two classes of ‘IT/IS’ systems, those which belong to the ‘reality’ and those which belong to the ‘actuality.’ To appreciate this distinction, we propose that this requires not only an understanding of the design of these IT systems but of the methodology of their use and their evaluation. To carry out the process of evaluation of IT/IS systems, we need to develop a new ‘appreciation’ methodology which enables us to rethink ‘IT/IS’ as ‘A system to use IT/IS.’ This idea is similar to the idea of Beck’s (World risk society theory (trans: Shimamura K), Chikuma Scholastic Collection (in Japanese), 2010) reflecting the modern. So, we propose a strict distinction between the two systems classes of ‘IT/IS’ which we call belonging to the ‘reality’ and ‘A system to use IT/IS’ which we call belonging to the ‘actuality.’ The methodology to deal with ‘actuality’ has not yet been developed, but Checkland and Poulter’s (Learning for action, Wiley, New York, 2006) soft systems methodology (referred to as SSM below) intends to deal with this kind of class of systems, that is, ‘human activity systems.’ He uses the key concept of ‘accommodation’ which means ‘to live with different individual world views based on sharing of actuality,’ and thus, he proposes to overcome the idea of consensus which is the agreement with the ‘reality’ level. In this paper, we adopt a methodology based on the SSM’s accommodation and not based on the consensus on the ‘reality’ level. By using such a methodological thinking, we reconsider the problem of evolving technologically a mature society which can be seen as a problem relevant to ‘A system using IT/IS’ rather than the problem of IT/IS itself. In doing so, we could draw some innovative orientations in the field of IT/IS which by traditional methodology could not be drawn. It is not certain whether our attempt could make a difference to the runaway of IT/IS. We illustrate this purpose by studying a workshop process which highlights that even participating experts of IT/IS themselves felt apprehensive about the more and more focus on the implementation of IT/IS solutions both in the present and the future. We believe that the first step toward this purpose is to explore the new orientation of IT/IS use. The aim of this first step is to make a difference to the ‘abnormal’ situation and hope to create a foothold for the reorientation of ‘A system to use IT/IS.’