Think Like a Contrarian: Use the Inversion Principle to Solve Smarter and Live Simpler
The Inversion Principle
Your brain is great at solving problems forward. But it’s world-class at messing them up in reverse.
Most people chase goals by asking:
“How do I get this outcome?”
But mental masters ask instead:
“How could I guarantee failure?”
This is the essence of Inversion, a thinking model used by thinkers like Charlie Munger and habit mavens like James Clear. It helps you uncover blind spots, stress-test decisions, and eliminate stupidity before it compounds.
Here’s what Munger said:
“All I want to know is where I'm going to die, so I’ll never go there.”
And for a little more practicslciy, Clear said, "The best way to start a new habit is to avoid the ones that conflict with it.”
Inversion doesn’t just make you smarter.
It makes your habits sharper. It makes your systems cleaner and life simpler.
In a way, it's kind of Zen. When in doubt?
Don’t add. Subtract.
How I Built Better Systems by Solving in Reverse
When I used to feel overwhelmed, I’d do what most people do: try harder, add more structure, stack more tools, and drown in to-do lists.
Then I flipped it.
Instead of trying to solve for productivity, I started asking:
“How could I guarantee staying stuck?”
Here were my answers:
Let email run my day
Say yes to everything
Never clarify outcomes
Do it all myself (no delegation)
Don’t block focus time and just go with the flow
I realized I was doing all five. No wonder I was drowning.
That week, I deleted 17 calendar events, rewrote my morning workflow, and said no to 3 meetings. And for the first time in a long time, I felt clear again.
Sometimes, the easiest way forward… is backward.
5 Ways to Use Inversion to Design a Better Life
1. Health:
→ Instead of “How do I get healthier?”
Ask: “How could I guarantee poor health?”
Eat out often
Stay up late
Be sedentary
Now reverse the pattern.
2. Time:
→ Instead of “How do I get more done?”
Ask: “How do I waste time?”
Check phone constantly
Keep the calendar wide open
Avoid deciding priorities
Now reverse the behavior.
3. Focus:
→ Instead of “How do I focus better?”
Ask: “How could I guarantee distraction?”
No boundaries
Let email and Slack be my boss
Skip breaks
Now reverse the system.
4. Relationships:
→ Instead of “How do I build better relationships?”
Ask: “How do I wreck them?”
Interrupt often
Avoid honest feedback
Be too busy to check in
Now invert to improve.
5. Business:
→ Instead of “How do I grow this company?”
Ask: “How would I ruin this business?”
Hire too fast
Ignore customer pain
Launch without testing
Use these insights to build safeguards.
The View From Upside Down
Inversion thinking might come off as negative, but it's really about opening up creative problem solving by coming at things from a new angle. Like looking out for the potholes before you hit them, or checking the weather before going on a long bike ride (I fail to do this all too often).
“Avoiding stupidity is easier than seeking brilliance.” – Charlie Munger
So next time you’re stuck, frustrated, or overwhelmed, give it a try. Instead of looking for what's missing, check out what can get removed.
Think backward, then move forward.
And maybe adopt it as a new habit.
Find your next edge,
Eli
