This paper looks at aspects of the development of Ecological Economic theory through the lens of second-order cybernetics. Ecological Economics aims to integrate Ecological and Economic disciplines while maintaining their distinction. This is required for the concept of “scale” which relates the size of the ecosystem with the size of the economy. Beyond the dynamic and complicated nature of these systems; this task is also conceptually difficult. How can the ecosystem be part of the economy but also distinct from it? How can the economic system be part of the ecosystem and also distinct? Which is the correct framing? While Ecological Economics was conceived in the era of “open systems” and “sub-systems”, second order systems theory may shed light on the paradoxes which naturally arise from this perspective. As second-order systems theory would suggest, this fundamental paradox of observation results in a circularity. This circularity can be illustrated by attempts within Ecological Economics to generate definitions of sustainability; most notoriously through valuation of ecosystem services but also within alternative social and ecologically based models. It may be possible to embrace this circularity and seek an “operational closure”. In the process of considering this, I reflect on my experience in studying Ecological Economics and Second-Order Cybernetics.