Ecological Economics has emerged across disciplines, and has begun to disentangle, not only the relationship between biophysical earth systems and economic activity, but also, fundamental relationships between objectivity, power, value, ethics, perspective and purpose. In part, this thesis represents an effort to illustrate basic transdisciplinary concepts necessary for understanding the project of Ecological Economics. At present, Ecological Economics is challenged by a seemingly infinite number of available considerations, with a relatively narrow repertoire of impactful mechanisms of control. Given this, it is apparent that the application of Cybernetics to Ecological Economics might provide insights. Cybernetics can help to lend concise language to manners for implementing control and also help to navigate the paradoxes which arise for self- regulating systems. While Cybernetics played an early role in the formulation of the relationship between the economy and an environment with available energy, second- order cybernetics can help to formulate the autonomy of Ecological Economics as a self-regulating system and shed light on the epistemology and ethics of circularity. The first article of this thesis identifies occasions when Ecological Economics has confronted circularity, and explores options moving forward. Ultimately, confronting paradox and circularity provide the means for the substantiation of Ecological Economics. The food system is prominent within Ecological Economics discourse. It serves as a good example of the ‘emergence’ of coordinated activity. In Cybernetics jargon, we can think of the ‘Food System’ as a symbol for the redundancy found in linked characteristics of particular Ecological-Economic inquiry. For instance, when we consider the food system we can be sure that we are dealing with resources that are essential, both rival and non-rival, excludable and non-excludable, and also highly sensitive to boundaries in scope, and scale, and thus highly sensitive to political and social change. In this sense, the food system acts as a symbol for the coordination of activity, and produces an output which is an input to the Ecological Economic ‘boundary’ between the Economy and the Ecosystem. The second article of this thesis provides an analysis of GHG emissions within the Chittenden County Foodshed. We conclude that urban agriculture, dietary change and agro-ecological production in concert, provide emission reductions which are not achieved when these options are considered separately. Given these conditions, we see mitigation beyond 90% of current emissions.