This book examines the constructive crossing between philosophy, semiotics, and economics. The complexity of current socioeconomic policy problems demands revision of our conceptual outlooks and recognition of the importance of fresh insights into Keynes and Hayek in the context of capitalism and globalization, contributing to unprecedented social, political, and environmental challenges. Their contributions to economic theory, policy making and philosophical foundations are reconsidered here using the semiotic approach of Charles S. Peirce.The book provides accessible discussions on the role of semiotics in social sciences. Approaching philosophical problems using a semiotic approach requires overcoming and redefining preconceived ideas and conceptualizations of such problems. Throughout this work, the combination of Charles Peirce’s philosophical background with Keynes’s and Hayek’s contributions, as influential economic thinkers, permits a multifaceted dialogue, creating new conceptual, theoretical and methodological frameworks, preparing the reader for relevant real-world debates. This text serves to renew the bond between philosophy, semiotics, and economics and to rethink the paths to complexity.