Constructivism has been an important program in contemporary philosophy, but cannot itself cannot provide sufficient context for grasping its key points. To fully understand its power and potential we must borrow tools from other programs: specifically, Charles Peirce and John Dewey’s pragmatism. By exploring these two pragmatists’ articulations of “generalization,” which I hold is the most crucial question in constructivism, their prospective contributions to constructivism can be brought to light. If, as I argue, constructivism can incorporate the lessons of pragmatism, then it can still be considered a highly workable interpretation of reality and of human endeavors.