Inversion Thinking

Redirect: For most risk-anticipation work, prefer thinking-pre-mortem — it produces a narrative prospective-hindsight pass that surfaces richer, more specific failure causes than a generic checklist. Use inversion only as a quick failure-mode enumeration on a scoped feature/design; for full plans, launches, or strategic decisions, pre-mortem is the stronger tool.

Trigger Card

When planning a scoped feature or design where optimism may be hiding risks:

1. State the goal clearly.
2. Ask: "How would I guarantee this fails?" — list 10+ concrete failure paths.
3. Convert the top 3-5 into explicit avoidance requirements. (e.g., "No plaintext passwords" → "Use bcrypt with work factor ≥ 12")
4. Verify the plan addresses each.

Skip if the task is small/reversible or if failure modes are already well-covered by existing checks. For full plans or launches, use thinking-pre-mortem instead.

Overview

Inversion thinking, championed by Charlie Munger and rooted in mathematician Carl Jacobi's principle "Invert, always invert," approaches problems by considering their opposite. Instead of asking "How do I succeed?", ask "How would I guarantee failure?" then avoid those paths.

Core Principle: "All I want to know is where I'm going to die, so I'll never go there." — Charlie Munger