The Intersection of Technology and Philosophy

After three decades architecting enterprise information systems, I've discovered that the most elegant solutions emerge when technical precision meets philosophical wisdom. I'm an Information Architect and Software Engineer specializing in AI-first language engineering—building custom Domain-Specific Languages (DSLs) that enable machines to understand and augment human expertise rather than replace it.

Technical Journey

Current Focus: Independent consultant specializing in Semantic AI Agents and agentic AI solutions. I architect systems using Langium, TypeScript, and Eclipse Theia to create unified development environments where language servers, diagram editors, and AI assistants work in concert.

Foundation: 30+ years in Microsoft technologies, including five years as a Microsoft MVP and founder of the SharePoint Developer Network (10,000+ members). My approach to information architecture—codified in my Structured Relational Mapping (SRM) methodology—transforms complex organizational knowledge into actionable intelligence.

Innovation: Patent applicant for Paragraph Management Software System. Developer of graphical notation for legal norms based on deontic logic and Hohfeldian analysis, with an expert system in LISP for natural language legal relationship recognition.

Academic Foundation

  • J.D. University of Michigan Law School
  • A.B. Applied Mathematics Harvard University

This unique combination enables me to bridge the precision of mathematical logic with the nuance of legal reasoning—essential for building AI systems that understand context, not just syntax.

Beyond the Code

Philosophical Practice: Student of Vedic philosophy under Sri Sri Ravi Shankar. I practice and teach Vedic meditation, finding that ancient wisdom provides essential perspective on modern technological challenges. My upcoming book, Truth Alone Triumphs (November 2025), applies timeless Vedic frameworks to contemporary American issues.

Creative Pursuits: Jazz fusion enthusiast (Pat Metheny, Yellowjackets, David Sanborn). Woodworker crafting custom furniture. Permaculture gardener designing regenerative systems on Amelia Island, Florida. Lifelong vegetarian.

What I Offer

I help organizations navigate the AI transformation by:

  • Building custom DSLs that encode domain expertise into executable specifications
  • Creating VS Code extensions and Eclipse Theia IDEs that amplify developer productivity
  • Architecting agentic AI systems that augment human intelligence
  • Transforming unstructured information into structured, queryable knowledge graphs

Current Projects

  • Language Engineering: Developing Langium grammars for legal analysis, regulatory compliance, records management, cybersecurity assessments, AI readiness, change management, and document composition
  • Book Launch: Truth Alone Triumphs - bridging Eastern philosophy and Western challenges
  • Technical Writing: Sharing insights on AI-first development at johnholliday.net

Connect

Based on Amelia Island, Florida, I work with clients globally who seek thoughtful, principle-driven approaches to technology transformation.

Email: john@johnholliday.net
LinkedIn: https://linkedin.com/in/holliday

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"Technology should amplify human wisdom, not replace it. The best systems emerge when we honor both ancient principles and modern possibilities."