This paper presents a discussion on the possibility of a dialectical and beneficial relationship between psychoanalysis and the new emerging influence of technology on self-representations. For this purpose, I will utilize Winnicott's concept of true and false self. The “quantified self” will serve as a digital case study for exploring the explanatory power of psychoanalytic concepts. After briefly describing the two concepts, “true\false self” and “quantified self”, I will try to illustrate the possible connections between them. My aim is to demonstrate how the psychoanalytic theory can illuminate still dark parts in the understanding of our new digital era and its impact on subjectivity. Finally, I wish to turn a critical gaze on psychoanalytic theory and its blind spot when coming to deal with digital technology and its growing inter-relatedness to self-representation. I will argue that developments in psychoanalytic theory have diminished its explanatory power by forsaking its moral compass in favor for a more relativistic point of view. A point of view that renders it incapable of serving as a beacon of light amidst a perilous and hazardous zeitgeist, like it once did.