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I'm slowly but surely forming a better idea how to do "better specs". The key idea is to make them structured and allowing a spec to contain structured source of truth definitions and rich artifacts such as code-defined diagrams, API/CLI/schema definitions, etc.

This could look something like "literate TypeScript". A mixture of TypeScript, Markdown and React. Think Jupyter Notebooks but modern and embracing web technologies. Still early days but I'm already working towards this spec-driven vision.