Inversion Technique
What if the fastest path forward is to figure out what guarantees failure — and walk the other way?
Avoiding stupidity is more reliable than chasing brilliance. You can't always know what will work, but you can almost always identify what will destroy you. Inversion exploits this asymmetry: negative knowledge is more robust than positive knowledge.
"Invert, always invert." — Carl Jacobi
Forward vs Inversion
| Dimension | Forward Thinking | Inversion |
|---|---|---|
| Starting question | "How do I succeed?" | "What guarantees failure?" |
| Knowledge type | Positive — what to do | Negative — what to avoid |
| Error profile | Misses hidden risks | Surfaces blind spots first |
| Cognitive bias | Confirmation (seek evidence you're right) | Forces confrontation with disconfirming evidence |
| Robustness | Fragile to surprises | Antifragile — removes what breaks |
The Method
| Step | Action | Question |
|---|---|---|
| 1 | Define the outcome | What does success look like, specifically? |
| 2 | Invert it | What would guarantee the opposite? |
| 3 | List failure causes | Which behaviors, decisions, or conditions produce that failure? |
| 4 | Check current reality | Which of these failure causes are present right now? |
| 5 | Subtract | Remove or mitigate each failure cause. What remains is a cleaner path. |
This combines Munger's inversion with Taleb's via negativa (progress by subtraction) and Gary Klein's pre-mortem (prospective hindsight).
Where It Works
Munger's prescription for misery. Harvard School commencement, 1986. Instead of telling graduates how to be happy, Munger inverted: "What would guarantee a life of misery?" His prescriptions: be unreliable, learn only from your own experience, stay down after setbacks, and refuse to think problems through backwards. The inverted framing is more memorable and more actionable than any positive advice — you can check yourself against four specific behaviors.
Amazon working backwards. Since 2004, Amazon teams write the press release and FAQ for a finished product before building anything. They start at the end — the customer experience of a shipped product — and work backwards to figure out what needs to be true. Teams write 10+ drafts. Most major Amazon products (Kindle, AWS, Prime) went through this process. Instead of "what can we build?", ask "what would the customer need to read to be excited?"
Bezos regret minimization. In 1994, Bezos was 30, working at D.E. Shaw. Web usage growing 2,300% per year. His boss walked him through Central Park for two hours and told him the internet idea was "really good... for somebody who didn't already have a good job." Bezos resolved it by inverting his time horizon: projected himself to age 80 and asked "will I regret NOT trying this?" He wouldn't regret failing. He would regret never trying. Temporal inversion — optimize against future regret, not present comfort.
The Shadow
Inversion is a filter, not a compass.
Paralysis by negativa. You can subtract indefinitely and end up with nothing. Knowing what to avoid does not tell you what to build. Passing all your negative screens isn't an indication of goodness — you still have to make a bet.
Pessimism bias. Chronic inversion trains you to see threats everywhere. The person who only asks "what could go wrong?" never ships. Munger used inversion AND forward reasoning — always both.
False equivalence. "Avoid failure" and "achieve success" are not symmetric. Some goals require positive action that no amount of subtraction will produce. You don't compose music by removing bad notes from silence.
The discipline: use inversion to clear the minefield, then use forward reasoning to move through it.
Connected Methods
| Method | Relationship | Shared Principle |
|---|---|---|
| First Principles | Both strip assumptions. First principles asks "what must be true?" Inversion asks "what must NOT be true?" | Question the default |
| Design Thinking | Empathy is soft inversion — stepping out of your perspective. "Reverse brainstorm" is explicit inversion. | See from the other side |
| Systems Thinking | Finding leverage through failure modes. Systems thinking asks "where are the loops?" Inversion asks "where do the loops break?" | Find where things break |
| Outsider Thinking | Both challenge the default. Inversion asks "what would make this fail?" Outsider asks "why are we doing this at all?" | Escape the frame |
Context
- Charlie Munger — Master of inversion across investing and life
- First Principles — Complementary decomposition from the positive side
- Decisions — Where inversion meets action
- Decision Journal — Document inverted reasoning for review
- Critical Thinking — Evaluating claims, including your own
- Opportunity Cost — Every choice inverts into what you gave up