Inversion Thinking: Solving Problems by Reversing Them

“Tell me where I’m going to die, so I’ll never go there.”
That’s a quote attributed to Charlie Munger, the billionaire investor and longtime partner of Warren Buffett. It’s also one of the clearest expressions of a mental model that has changed the way I solve problems, make decisions, and lead.

It’s called inversion.

And if you’re serious about improving your results—professionally or personally—you need to add it to your mental toolkit.

WHAT Is Inversion?

Inversion is a problem-solving and decision-making strategy where instead of asking, “How do I succeed?”—you ask, “How could I fail?”

Instead of pursuing the right path, you look for the wrong ones—and avoid them.

Instead of building a plan forward, you reverse-engineer it backward.

Inversion flips the question. It removes blind spots. It uncovers hidden risks. And it often reveals clearer, more actionable steps than forward-only thinking ever could.

It’s not negative thinking. It’s preventative thinking.

WHY Inversion Works (and Why You Should Use It)

Most people try to achieve success by asking, “What should I do?”

Smart people also ask, “What should I not do?”

Inversion works because:

1. It exposes hidden risks.
   We overlook things when focused only on best-case outcomes.
2. It builds resilience.
   Thinking backward highlights weak links and blind spots.
3. It simplifies complexity.
   It’s often easier to define failure and work backwards than to predict every step to success.
4. It improves strategy.
   Businesses that only plan to win often ignore what could destroy them.
5. It clarifies priorities.
   You stop trying to optimize every little thing and focus on avoiding catastrophic missteps.

Inversion helps you build anti-fragile plans—plans that don't just work when things go right, but stay strong even when things go wrong.

WHO Should Use Inversion?

Inversion is not just for CEOs and investors.

It’s for:

• Entrepreneurs avoiding costly mistakes
• Managers leading through uncertainty
• Marketers anticipating campaign failure points
• Engineers preventing system collapse
• Parents teaching critical thinking
• Students studying smarter
• Anyone who sets goals and makes decisions

In short, if you’re in the game of solving problems, inversion gives you an edge.

And yes, this is something they absolutely teach in top-tier MBA programs under the umbrella of critical thinking and decision-making models.

WHEN To Use Inversion

Here are some prime moments for inversion:

• Before launching a new initiative
  Ask: “How could this fail?”
• During strategic planning
  Ask: “What would cause us to miss our goals?”
• When making a big personal decision
  Ask: “How could I regret this later?”
• When stuck in analysis paralysis
  Ask: “What’s the worst move I could make?”
• When coaching a team or mentee
  Ask: “What would definitely lead you to burnout or failure?”

Inversion is particularly powerful in complex, high-stakes, or uncertain situations.

WHERE Inversion Applies

Inversion thinking applies everywhere. Here are a few domains:

Business

• Designing a customer experience:

What makes people stop using us?

• Marketing strategy:

What would make this ad flop?

• Hiring:

What type of hire would ruin our team culture?

• Scaling:

What would break if we doubled in size overnight?

Life

• Fitness:

What would sabotage my health goals?

• Finances:

How do people end up broke in retirement?

• Relationships:

What behaviors destroy trust?

• Education:

What stops people from learning or applying knowledge?

Personal Growth

• Productivity:

What wastes time every day?

• Decision-making:

What would I regret not considering?

• Reputation:

What would cause people to stop trusting me?

Inversion reveals that failure isn’t always sudden—it’s often the result of accumulated small mistakes we didn’t see coming.

HOW To Use Inversion (Step-by-Step)

Let’s get tactical. Here’s how to apply inversion right now.

Step 1: Define the Goal Clearly

Ask yourself:

What outcome do I want?

Make it specific. For example:

• Launch a successful online course
• Improve team performance
• Lose 15 pounds
• Retire at 55
• Improve customer retention
• Increase revenue by 25%

Step 2: Invert the Goal

Now flip it:

What would completely destroy this goal?

Ask:

• What are the dumbest decisions I could make?
• What are the common mistakes others make here?
• What behaviors, assumptions, or habits would guarantee failure?

Write them out.

Step 3: Analyze the Inverted List

Now study the list:

• Are you already doing any of these things?
• Are you flirting with any of these risks?
• Are you ignoring any weak points?

Look for:

• Blind spots
• Structural weaknesses
• Behavior patterns
• Misaligned incentives

Step 4: Build Safeguards

Now take preventative action:

• Remove the failure pathways
• Add contingencies
• Create boundaries
• Design systems that prevent self-sabotage

Inversion doesn’t just show you what to avoid—it guides what to build.

Step 5: Review Regularly

Return to inversion as a thinking tool, not a one-time trick.

Use it:

• In quarterly reviews
• After major changes
• During reflection
• As a coaching tool for others

You’ll catch mistakes earlier and navigate with more confidence.

Example: The Inverted Business Plan

Let’s say you’re launching a coaching business.

Your goal: $100K in revenue in your first year.

Invert it:
What would ensure you fail?

• You never talk to customers
• You assume your niche without testing
• You underprice yourself out of business
• You create a product nobody asked for
• You rely on one channel for all your traffic
• You don’t track your metrics
• You get discouraged after the first failed launch

Now, flip those into to-dos:

• Interview 10 ideal clients
• Validate offer with pre-sales
• Price based on value and margin
• Diversify traffic sources
• Build in debriefs after every launch
• Track leading indicators weekly

Suddenly, you have a strategy based on avoiding failure, not just hoping for success.

Personal Example: Inverting My Own Growth

Early in my career, I used to ask:

“What do I need to learn to succeed?”

Now, I ask:

“What do people do that keeps them stuck?”

The list is long:

• Waiting for permission
• Consuming more than producing
• Avoiding hard conversations
• Blaming others
• Wasting time on things that don’t move the needle

Avoiding those habits—consciously and consistently—did more for my results than any fancy new hack or course.

Pitfalls to Avoid

A few common traps:

1. Mistaking inversion for negativity
   It’s not pessimism—it’s protection.
2. Stopping at the problem list
   Inversion only works if you take action to avoid the pitfalls you uncover.
3. Over-inverting and never starting
   Don’t let inversion lead to overthinking or analysis paralysis.
4. Using it only solo
   Inversion works great with teams. Ask your people: “What would cause this plan to fail?”

Bonus: Combine Inversion With First Principles

You can pair inversion with first-principles thinking for powerful clarity.

Example:

• First Principle: “A business makes money by solving problems.”
• Inversion: “A business dies by ignoring problems or solving the wrong ones.”

Boom. Now you’re thinking strategically.

Final Thought: Flip the Question, Find the Answer

The world rewards results—not just effort or optimism.

And the people who win consistently aren’t the ones with the best plans…
They’re the ones who avoid the worst mistakes.

Inversion helps you see the cracks before they collapse.
It helps you learn from others’ failures, instead of repeating them.
It helps you build strong, simple, smart systems that work.

So the next time you ask yourself, “What should I do?”
Try flipping it.
Ask: “What would be the dumbest thing I could do?”

Then do the opposite.

That’s inversion.
And that’s how you win by not losing.