Flip the Problem: Why Inversion Thinking Might Be Your Smartest Strategy Yet
If you’ve ever caught yourself asking,
“What should I do?”,
let me suggest a better question:
“What would completely screw this up?”
That’s the power of inversion thinking.
It’s one of the simplest, most powerful mental tools I’ve ever used—and one that separates amateur thinkers from strategic ones.
What Is Inversion?
Inversion is flipping the problem on its head.
Instead of asking:
“How do I succeed?”
You ask:
“How would I fail?”
“What’s the dumbest move I could make?”
“What mistakes would destroy this?”
Then you avoid those mistakes. Simple.
Inversion doesn’t guarantee success.
But it helps you prevent failure, which is often even more important.
Why It Works
Most people focus only on best-case scenarios. That’s a trap.
Inversion:
- Exposes blind spots
- Surfaces hidden risks
- Clarifies what really matters
- Forces you to get real about what can go wrong
- And helps you build plans that are resilient, not just optimistic
As Charlie Munger once said:
“Tell me where I’m going to die, so I’ll never go there.”
That’s inversion thinking in one sentence.
Who Should Use It?
Anyone making decisions, solving problems, launching ideas, or trying to grow—personally or professionally.
Entrepreneurs.
Leaders.
Coaches.
Parents.
Students.
You.
Yes, this is something they teach in MBA programs—because it works.
How to Use It
Let’s say your goal is to build a successful side hustle.
Instead of asking, “What do I need to do?” try this:
Invert it:
“How would I fail at this?”
You might list:
- Choosing a niche nobody cares about
- Never talking to customers
- Underpricing myself
- Quitting after the first failure
- Spending all my time building, not selling
Then you build your plan to avoid those mistakes:
- Validate your niche
- Talk to people early and often
- Price based on value
- Normalize failure
- Sell while you build
See how this works?
Inversion = strategic clarity.
Use It for Personal Growth Too
Trying to get in shape?
What ruins most fitness efforts?
Bad sleep, stress, unrealistic plans, no support, junk food at home.
Avoid those first.
Trying to improve your career?
What holds most people back?
No plan. No mentors. Bad communication. Burnout. Blame.
Avoid those traps—and suddenly, the path forward is clearer.
Try This This Week
- Pick a goal or challenge.
- Flip the question: “What would guarantee I fail?”
- Make a list.
- Turn that list into action steps to prevent failure.
You’ll see the problem in a whole new way.
Final Thought
Inversion doesn’t replace good planning. It sharpens it.
And in a world where most people rush forward…
You’ll stand out by stepping back and asking:
“What would be the dumbest thing I could do?”
Then just… don’t do it.
Sometimes the smartest move is simply avoiding the stupid ones.
That’s inversion. And it’s how you stay sharp.
Want to read the full article? Find it here.
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