Eugen Bleuler, the founder of the concept of schizophrenia, pointed out that psychotic patients were able to live in two disjoint worlds (namely, the social, intersubjective world and the delusional world). He termed this phenomenon “double bookkeeping,” but did not provide any conceptual elaboration of this phenomenon or its possible mechanisms. Double bookkeeping has been neglected in mainstream psychiatry, but it has been addressed in recent theoretical work, however mainly concerned with the issue of delusion. In this article, we present clinical material that supports the view that double bookkeeping manifests itself across various psychotic phenomena and its antecedent may be observed in premorbid (pre-onset) phases as well as in the schizotypal disorder. We try to conceptualize double bookkeeping to concretize an often atmospheric perception of paradoxicality in the encounter with the patient. A phenomenological analysis of double bookkeeping suggests an instability in the affective (“auto-affection”) articulation of selfhood. We point to four main implications of our presentation: (1) diagnostic, (2) epistemological, (3) therapeutic and (4) pathogenetic research.