We talk with Jabe Bloom about how building software in enterprise is a philosophical argument and how knowing some philosophy can help. What is a pharmakon, and what is the Goldilocks space of complexity. Technical debt as an example of how deterministic systems can have agency within a socio-technical system. The origin story of Jabe’s model of the three economies and how it helps budgeting complexity and how it is a key to building successful platforms. Jabe currently works as a Senior Director in the Global Transformation Office at RedHat. Jabe has been transforming and researching the organizational dynamics and interactions of management, design, development, and operational excellence for over twenty years as an executive, academic and consultant. Jabe is also in the final stages of writing his PhD dissertation at Carnegie Mellon in transition design.