tooling

In the rapidly shifting landscape of AI-assisted development, your current stack is always decaying. To remain at the frontier, you must transition from “using tools” to “maintaining a discovery ritual.” This ritual is the engine behind the Tooling Chaos Monkey—it provides the candidates for your regular tool swaps. The Strategy: Models vs. Harnesses To do effective discovery, you must distinguish between the Model (the brain) and the Harness (the body/agent/IDE). Harness: Tools like Claud Code, Cline, Roo Code, OpenHands, or Droid. They provide the tool-use logic, environment access, and UI. Models: The underlying LLMs (Claude 3.5, GPT-4o, Gemini 1.5). A breakthrough can happen in either. A great model can fail in a poor harness, and a clever harness can make a mediocre model shine. ...

The Concept Applying the principles of Chaos Engineering to the developer toolchain. Just as Netflix’s Chaos Monkey randomly terminates instances to ensure system resilience, a Tooling Chaos Monkey involves intentionally and regularly disrupting your own development environment—disabling or swapping out key tools—to ensure workflow independence and adaptability. Why Do It? Prevent Lock-in: Deep reliance on a specific tool (e.g., a specific AI coding assistant’s proprietary features) creates a vulnerability. If that tool changes pricing, disappears, or degrades, your productivity shouldn’t crash. Accelerate Learning: New tools often introduce new paradigms. Regularly switching (e.g., from VS Code to Zed, or Copilot to Claude Sonnet) forces you to learn new capabilities and keeps your “tool plasticity” high. Validate Workflow Robustness: If your workflow breaks because you can’t use a specific button in a specific IDE, your workflow is fragile. True productivity comes from patterns that transcend tools. Implementation: The “Break One Tool” Drill Regularly (e.g., once a sprint or simply “on Tuesdays”), simulate a failure of a primary tool: ...