Inversion
Find the ways something could fail, then make sure you don’t do them.
What would guarantee failure?
Reach for it when
- You’re starting a project, plan or launch with real stakes.
- Forward thinking gives only vague answers like “work hard”.
- Everyone is optimistic and nobody is naming the risks.
- You keep making the same kind of mistake.
- You need a checklist for something that must not go wrong.
Put it down when
- You need a bold new idea. Avoiding failure won’t generate one alone.
- It’s turning into anxiety, listing every possible disaster without acting.
- The cost of failure is tiny. Just try it.
The framework
- Name the goalBe specific about what success would look like.
- Flip itAsk: what would guarantee failure? Imagine it has already failed.
- List the causesWrite every reason, especially awkward ones about people and yourself.
- Rank by likelihood and harmFocus on what is both likely and damaging.
- Invert each into a ruleTurn every major cause into a specific action or guardrail.
- Review regularlyRevisit the checklist at each milestone; new failure modes appear.
Rules of thumb
- Avoiding stupidity is easier than seeking brilliance.
- Specific failures make specific rules. Keep them concrete.
- Include failures caused by you, not just by bad luck.
- Use inversion to clear the path, then think forward to choose the route.
Questions to ask yourself
- What would guarantee this fails?
- If this failed a year from now, what would the reason be?
- What am I doing now that the failure version of me would also do?
- What would my harshest critic say goes wrong?
Common traps
- Listing only outside risks and none of your own habits.
- Writing vague rules like “communicate better”.
- Running the exercise once, then never looking at it again.
- Mistaking “nothing went wrong” for “it went well”.