The ongoing development of information technology creates new and immensely complex environments. Our lifeworld is drastically influenced by these developments. The way information technology is intertwined in our daily life raises new issues concerning the possibility of understanding these new configurations. This paper is about the ways in which IS research can contribute to a deeper understanding of technology and the ongoing transformations of our lifeworld. As such, the paper is a conceptual exploration driven by a sincere and authentic desire to make a real difference in the way research on how technology influences our society is carried out. The article is based on the assumption that there are some foundational decisions forming research: the question of methodology, the question of object of study, and, most importantly, the question of being in service. In the paper we explore and propose a research position by taking a critical stance against unreflective acceptance of information technology and instead acknowledge people’ s life-world as a core focus of inquiry. The position is also framed around an empirical and theoretical understanding of the evolving technology that we label the digital transformation in which an appreciation of aesthetic experience is regarded to be a focal methodological concept.