About five years ago, I found myself obsessing over all the ways not to fail at a new business venture. That unorthodox approach—listing the pitfalls rather than dreaming up the perfect plan—unexpectedly led me to the mental model of inversion. If you’ve ever wondered how Sherlock Holmes cracks impossible cases or why Charlie Munger famously says, "Invert, always invert," you're about to discover how this upside-down thinking becomes a secret weapon for solving life’s stickiest problems.
Why Inversion Crushes Conventional Problem-Solving
When faced with a tough challenge, our instinct is usually to charge straight at the solution. We brainstorm answers, list strategies, and map out plans. But what if the smarter path is to work backward—from failure to insight?
This is the essence of inversion: instead of asking how to succeed, you ask how to fail. Then, by avoiding those failure points, you dramatically increase your odds of success. The roots of this model trace back to the 19th-century mathematician Carl Jacobi, who advised, "Invert, always invert" — a strategy that turns complex problems on their head to make them more manageable.
Charlie Munger, the legendary investor and vice chairman of Berkshire Hathaway, exemplifies this philosophy. His advice:
“All I want to know is where I’m going to die so I’ll never go there.”
Munger's wisdom flips conventional thinking: instead of chasing wins, focus on avoiding losses. In today’s chaotic world, this mental judo is more powerful than ever.
Take wealth building. Most people ask, “How do I become rich?” The answers are endless—real estate, startups, crypto. But inversion reframes the question: “How do people go broke?” The answers are clearer: overspending, not saving, poor investments, ignoring learning. By avoiding these, you naturally move toward wealth.
The same holds for relationships. Don’t ask, "How do I get people to like me?" Ask, "What behaviors push people away?" Avoiding dishonesty, unreliability, and lack of empathy will get you further than any charm tactic.
Inversion also shows up in assumption-based reasoning. Think of Albert Einstein, who inverted scientific norms by assuming the speed of light is constant. That mental reversal unlocked the theory of relativity. You don’t need to be Einstein to benefit from this method.
When stuck, flip the problem: Assume the opposite. What would have to be true for the worst outcome to occur? This reveals hidden risks and new strategies often missed by a forward-only approach.
Inversion isn’t about pessimism. It’s about proactive clarity. It focuses your attention on what matters most: avoiding the obvious traps.
From Victorian Detectives to Modern Boardrooms: Inversion in Action
If you’ve ever admired Sherlock Holmes’ razor-sharp logic, you’ve seen inversion in action. Holmes solved mysteries by systematically ruling out the impossible, saying:
“When you have eliminated the impossible, whatever remains, however improbable, must be the truth.”
Inversion isn't just for detectives. It’s deeply embedded in science, strategy, and decision-making.
In business, leaders use inversion to reverse-engineer failure. This is the basis for pre-mortems: imagine a project has failed, then work backward to identify what caused it. This uncovers hidden risks early, giving teams a chance to prevent them.
For example, rather than focus only on growth tactics like launching a product or entering a new market, inversion asks: “What would guarantee this launch fails?” The answers—poor market research, ignored feedback, bad timing—become your risk checklist.
This mindset can also reframe your career path. Instead of asking, “How do I get promoted?” ask, “What would guarantee I never get promoted?” Then avoid those behaviors: missing deadlines, refusing feedback, acting unethically.
Whether you’re solving crimes, managing teams, or making life decisions, inversion forces you to challenge assumptions, uncover blind spots, and surface hidden insights.
Don’t Build Castles—Avoid Quicksand: Applying Inversion to Daily Life
The best way to build a solid foundation in life? Avoid the quicksand.
Inversion is a simple yet powerful tool for everyday decisions. Instead of obsessing over the "best" choice, ask, "What would be the worst choice—and how do I avoid it?"
Let’s say you want to improve your health. Forget the latest fitness hack for a moment. Ask: “What would ruin my health?” The answers are obvious: neglect sleep, overeat junk, never exercise, ignore stress. By sidestepping these behaviors, you're already ahead.
This same principle works in relationships (“What destroys trust?”) and finances (“What guarantees I end up broke?”). You don’t need to get everything right—just avoid what’s clearly wrong.
A useful inversion question before any decision: "What’s the dumbest thing I could do here?"
That one question alone cuts through complexity and sharpens judgment.
Create your own "Never Do" list. Examples:
Never check email first thing in the morning.
Never skip family dinners.
Never invest in something I don’t understand.
This kind of rule-setting gives structure to your daily habits. It removes noise and creates clarity.
Remember: In a world obsessed with growth hacks and shiny tools, sometimes the smartest move is subtraction. Eliminate the wrong paths, and the right one often reveals itself.
TL;DR Key Takeaways
Flip your problems on their head. Instead of chasing success, avoid failure. The inversion mental model helps you make smarter decisions, avoid traps, and reveal hidden solutions. Used by thinkers like Charlie Munger, Carl Jacobi, Sherlock Holmes, and Einstein, it’s not about pessimism—it’s about strategic clarity.
