Quantification, the measurement and representational modeling of objects, events and relationships, cannot enhance life quality, not directly. Illustrative is Sydenham’s model of disease (Sydenham, 1848-1850) and its spawn: the checklist quantification that is contained in the DSM (Diagnostic and Statistical Manual of Mental Disorders, now in its fifth edition) and ICD (International Classification of Diseases, now in its ninth edition). The use of these diagnostic catalogs is incapable of directly enhancing health, a component of life quality; because health is not the control or absence of disease, and practitioners do not think in checklists. Healthcare practitioners have adopted the methods of the airline industry in imposing checklists that are unnatural to nonlinear cognition. At first instance and finally, the subjectivity of experience and the intersubjectivity of communication create the diagnostic and therapeutic relationship that enhances health and life quality. Health is the capacity to cope and to adapt to the experience of suffering, regardless of its cause or context, and to pursue salutary experience. Society will effectively develop, implement and “reform” healthcare only when it accepts positive, noncircular definitions of health and “Quality of Life.” The ethical obligation of the practitioner is to honor and trust the patient’s narrative of illness, the story of suffering.