In this vivid discourse, John Bellone and Jeremy Rossi delve into the nuanced world of software development, exploring the often overlooked aspects of complexity in technology. Their conversation spans several critical areas, including the challenges of understanding and addressing complexity, the impact of tech debt and legacy systems, and innovative ways to manage and communicate about complexity through technology. Highlighting examples from government infrastructure to modern software deployments, they dissect the multifaceted layers of complexity that pervade decision-making and operational efficacy in technology projects. Through engaging dialogue, they offer insights on employing frameworks, tools, and methodologies—such as protobuf, gRPC, and Backstage.io—to navigate and mitigate complexity, underscoring the importance of schema, version control, and the human element in technology development.