The challenge of this essay is to outline a transdisciplinary context of human and technological agents acting and making decisions as parts of complex real-world systems. The general focus is on health care and rehabilitational settings, supported by mobile, context-aware information technologies. There is a growing need to empirically test and simulate decision-making in smart environments – both qualitatively and quantitatively, e.g. to analyze both socio-economic and technological properties of these network systems. The Holistic Concept of Man Metaphor as a model of a human decision maker is juxtaposed with agent paradigms. Consequently, many ethical questions arise.