A chronological evolution of my relationship with artificial intelligence, moving from individual productivity to cognitive architecture.
Phase 0: Foundations
Pre-2023
5+ years at Datadog, culminating as a Senior Technical Escalation Engineer. Deep expertise in observability and the integration of thousands of enterprise cloud environments. The realization that complex systems require high-fidelity context—not just data—to operate reliably.
Phase I: The Addiction of Leverage
Late 2023 - Early 2024
Falling down the rabbit hole. This phase was about discovering the raw power of LLMs and building tools to solve personal bottlenecks.
- 🛠 Automated top-of-funnel job search via scraping and AI qualification.
- 🛠 Natural language to grocery cart automation.
- 🛠 **Personal R&D:** Deep dive into GCP, Docker, and Playwright orchestration.
Phase II: The Architecture of Context
Mid 2024 - Present
Realizing that the bottleneck wasn't execution, but decision-making. The pivot to architecting the context in which AI operates.
- 🧠 A strategic alignment engine that synthesizes long-term plans into daily tasks.
- 📈 A modular, event-driven quantitative wealth building system.
- 🏗 CLI-native orchestration across multi-repository environments.
Phase III: The Great Inversion
The Future
Moving from "How" to "Why." Using AI to clarify values and automate the path to strategic sovereignty.
READ THE PHILOSOPHY IN THE RABBIT HOLE →Key Methodology: Recursive Inference
The practice of consistently applying AI to the meta-problem rather than the problem at hand. By staying in the most leveraged position, we reserve our own cognitive energy for the highest-level architectural decisions.