The purpose of this study is to figure out psychological and educational measurement from the perspective of the philosophy of science and its practice. The philosophy of measurement was considered as a common ground between psychological/educational measurement and the philosophy of science. Measurement is not only for describing the world but also an essential tool for describing our thoughts. To discuss the philosophy of measurement through conceptual analysis, I first examined assumptions about the ontology and epistemology of true knowledge to establish a philosophy of measurement. I found that I hold to the views of ontological realism and epistemological constructivism for both the physical and psychological/educational sciences. On the basis of my assumptions about knowledge, I found “constructive realism” to be a supportable philosophy of measurement. From the results of conceptual analysis, I found that constructive realism works well in both the physical and psychological/educational sciences. For practice underpinned by constructivist realism, I identified the four building blocks of the Berkeley Evaluation and Assessment Research (BEAR) System as a solid, practical framework for psychological and educational measurement. These are cycles of measurement processes, the whole process of which is embodied within the nomological network of the conceptual foundations of constructivist realism. Constructive realism and the BEAR assessment system building blocks can give us both coherent and different accounts of the measurement process between the psychological/educational and the physical sciences. Philosophical arguments and practical suggestions from this study could serve to inspire psychological and educational academic circles, particularly with respect to the philosophy of measurement.