Even if the concept of organization is increasingly recognized as crucially important to (philosophy of) biology, the fear of thereby collapsing into vitalism, understood as the metaphysical thesis that “life” involves special principles irreducible to (and that perhaps even run counter to) the principles governing the physical order, has persisted. In trying to overcome this tension, Georges Canguilhem endorsed an attitudinal form of vitalism. This “attitudinal stance” (a term coined by Charles Wolfe) shifts the issue of organization away from ontological commitments regarding the nature of things as they are in themselves, in favor of epistemological issues concerning the stance of the knowing subject. However, it is based on some epistemological tenets that deserve further examination. Firstly, in spite of its anti-Cartesian spirit, the attitudinal stance implicitly relies on a Cartesian perspective on the relation between subject and object. Secondly, it rests on the idea that some objects can meaningfully be identified as persisting individuals—living organisms—in a way in which others cannot, even if it denies that the capacity to be meaningfully identified as such reflects an actual property of them. This chapter outlines a possible alternative viewpoint that takes these challenges to heart by developing a co-constitutive picture of the relation between subject and object—a picture based on Georges Canguilhem’s own theory of judgment, but supplemented by Immanuel Kant’s transcendental logic. Most fundamentally, it is argued that the (self-)organization of living beings draws attention to and is structurally intertwined with the (self-)organization of the thinking subject’s rational (i.e., logical, conceptual, judging) capacities.