Inversion

Think backwards to avoid failure - sometimes it’s easier to avoid stupidity than seek brilliance.

The Core Idea

Inversion is the practice of approaching problems from the opposite direction. Instead of asking “How do I succeed?”, ask “How could I fail?” By identifying what would cause failure, you can deliberately avoid those paths.

Key Principles

Flip the Question Turn problems upside down. Instead of “How do I build wealth?”, ask “How do I guarantee poverty?” The answers often reveal blind spots.

Avoid Stupidity Over Seeking Brilliance It’s often easier to avoid obvious mistakes than to find optimal solutions. Success is as much about avoiding failure as achieving excellence.

Negative Visualization Imagine the worst outcomes and work backwards to understand what causes them. This reveals risks you might otherwise overlook.

Applications

Decision Making Before committing to a path, ask “What would make this fail?” List all the ways something could go wrong, then design around those failure modes.

Goal Setting Instead of only defining what you want, define what you definitely don’t want. Avoiding anti-goals can be more clarifying than pursuing goals.

Problem Solving Stuck on a problem? Invert it. Can’t figure out how to increase sales? Ask “What would definitely decrease sales?” and do the opposite.

Risk Management Identify failure modes before they occur. “What could kill this project?” reveals vulnerabilities you need to protect.

The Process

1. State your goal - What are you trying to achieve?
2. Invert the question - How could you guarantee failure or the worst outcome?
3. List the anti-goals - What would definitely lead to failure?
4. Avoid those paths - Design your approach to eliminate or mitigate these failure modes
5. Check your blind spots - What assumptions about success might you have missed?

Examples

Building a successful company:

• Normal thinking: What makes companies succeed?
• Inversion: What kills companies? (Running out of cash, building what nobody wants, toxic culture, ignoring customers)
• Action: Structure your company to avoid these failure modes

Living a good life:

• Normal thinking: What brings happiness?
• Inversion: What creates misery? (Poor health, bad relationships, financial stress, lack of purpose)
• Action: First eliminate sources of misery, then pursue happiness

Making good investments:

• Normal thinking: What stocks will go up?
• Inversion: What would cause me to lose all my money? (Leverage, following crowds, ignoring fundamentals, emotional decisions)
• Action: Build rules that prevent catastrophic mistakes

Working With Inversion

• Use when forward thinking feels unclear or overwhelming
• Particularly powerful for risk assessment
• Combine with other mental models for comprehensive understanding
• Don’t only think negatively - balance with positive visualization
• Apply to both big decisions and daily habits

Common Pitfalls

• Focusing only on avoiding failure without pursuing success
• Becoming paralyzed by all the things that could go wrong
• Stopping at surface-level inversions
• Failing to act on the insights revealed by inversion

“Invert, always invert.” - Carl Jacobi

“It is remarkable how much long-term advantage people like us have gotten by trying to be consistently not stupid, instead of trying to be very intelligent.” - Charlie Munger