Douglas Engelbart's 1968 "Mother of All Demos" revolutionized the way we interact with complex information and laid the groundwork for modern software development by introducing concepts such as graphical computing, interactive real-time collaboration, and dynamic document editing. As software systems became more complex, visualization and modeling techniques evolved from simple flowcharts and Data Flow Diagrams to the Unified Modeling Language (UML), which standardized software design documentation to address challenges like physical distribution and concurrency. However, with the rise of Agile methodologies, the rigid structure of UML lost favor, giving way to more flexible tools like digital whiteboards and lightweight diagrams, which have since been enhanced by diagram-as-code solutions such as PlantUML and Mermaid.js. The latest shift involves leveraging real-time observability data to create automated, dynamic system visualizations, exemplified by tools like Multiplayer, aligning with Engelbart's vision of offloading cognitive complexity and enabling more effective collaboration and understanding of evolving software architectures.