Strange Looping
Artificial intelligence doesn’t exist in isolation—it evolves through deliberate construction within organizational contexts. Strange Looping documents the bootstrapping of AI constructs: how we build systems that think with institutional wisdom, and how these constructs reshape the organizations that create them.
Douglas Hofstadter described a strange loop as a self-referential system—one that folds back on itself in a way that creates stable identity. The AI constructs emerging in enterprise contexts are similar recursive systems, but they’re not emerging by accident. They’re being deliberately engineered, and will change the organizations that create them.
Through frameworks, case studies, implementation notes, musings, and back castings, Strange Looping explores the practical work of building AI constructs that serve human flourishing. It’s field notes from someone bootstrapping organizational intelligence—the technical, ethical, and strategic decisions that shape how AI systems learn to think alongside humans.
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Position Description: Strategic Dialogue Architect
Bootstrapping a Corporate AI in 2025
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