This paper focuses on Kant’s and Schopenhauer’s models of self-consciousness and their specific relation to time. It aims to show that genuine philosophical theories can explain the idiosyncratic relation between ourselves and the world without relying on pure metaphysical speculations or strictly empirical and phenomenally oriented conceptions, as many contemporary proponents of analytic philosophy entail. The first groundbreaking doctrine in this regard is Kant’s transcendental theory of apperception, which unfolds a new theoretical dimension of thinking, grounding the logical unity of thought in the pure, originally synthetic unity of the subject itself. In order to constitute a structural order within the appearing phenomenal world, Kant conceptualizes a theory of self-affection in the second edition of the Critique of pure reason , positing a dynamic relation between the spontaneously acting intellect and the purely receptive inner sense of time as a result of productive transcendental imagination. The problematic relation between self-reliance and empirical consciousness that Kant did not resolve completely led to various subsequent transformations of Kant’s transcendental principles, one of which boasts Schopenhauer as a prominent but rarely considered representative. Schopenhauer’s systematic approach consists in a modified version of Kant’s transcendental idealism, which ties the Kantian subject of logical and transcendental unity to an intuitive corporeal individual that can only conceptualize itself as an original, willing subject. The Schopenhauerian subject unfolds its empirical character in accordance with its own inner impulses and motivations, which manifest themselves in time but can only be interpreted as a phenomenal representation of a higher, metaphysical unity, which Schopenhauer calls the will as a thing in itself. Schopenhauer reaches his final metaphysical conclusion via a problematic analogy, positing another perspective on the corporeal nature of the individual which, by means of abstraction, can be extended to the whole phenomenal world. Therefore, Schopenhauer interprets the underlying (intelligible) character of the subject and the phenomenal world as a whole as a timeless, omnipresent will to live which can be temporally experienced within the nature of our own subjectivity.