Lesson 2: Inversion - Thinking Backwards

The Power of Thinking in Reverse

Have you ever noticed how some of the most brilliant solutions seem obvious in hindsight, yet they eluded everyone looking at the problem head-on? There’s a reason for this: most of us are trained to think forward—to start with what we have and work toward what we want. But some of the most powerful insights come from thinking in reverse.

Welcome to inversion, a mental model championed by brilliant thinkers like mathematician Carl Jacobi, who advised “invert, always invert” when tackling difficult problems, and Charlie Munger, Warren Buffett’s business partner, who considers it essential to avoiding catastrophic mistakes.

Inversion isn’t about being negative—it’s about being thorough. By looking at problems from both the front and the back, you develop a more complete understanding and often discover solutions that would otherwise remain hidden.

Why Inversion Works: The Psychology Behind It

Our brains have evolved with certain biases that make forward-thinking the default:

• We naturally focus on addition rather than subtraction (adding new features rather than removing obstacles)
• We’re more motivated by achieving success than avoiding failure
• We tend to anchor on our initial approach to a problem

Inversion helps us overcome these biases by deliberately shifting our perspective. It’s like walking around to the other side of a building—suddenly you can see windows and doors that were invisible from your original vantage point.

Additionally, inversion helps us overcome the planning fallacy (our tendency to underestimate time and resources needed) by forcing us to confront potential obstacles before we begin.

The Two Faces of Inversion

Inversion can be applied in two powerful ways:

1. Goal Inversion: Defining Success by Avoiding Failure

Instead of asking, “How do I achieve my goal?” ask, “What would guarantee I fail to achieve my goal?”

This approach is particularly valuable because: - It’s often easier to identify what would cause failure than what would ensure success - It helps you recognize and eliminate obvious mistakes - It reveals “invisible” assumptions you might be making

2. Problem Inversion: Reversing the Problem Statement

Instead of solving the original problem, solve its inverse and then invert the solution.

For example: - Instead of asking “How do I find great employees?” ask “How would I design a hiring process that consistently selects terrible employees?” Then do the opposite. - Instead of “How do I increase customer satisfaction?” ask “What would reliably drive our customers away?” Then avoid those things.

Practical Inversion Techniques

Let’s explore specific techniques you can use to apply inversion to your challenges:

Technique 1: The Pre-Mortem

Developed by psychologist Gary Klein, a pre-mortem works like this:

1. Imagine your project or decision has failed spectacularly
2. Write a detailed “history” of what went wrong
3. Work backwards to identify what could have caused this failure
4. Develop preventative measures for each potential cause

Unlike a traditional risk assessment that might feel abstract, a pre-mortem creates a vivid scenario that makes potential problems more concrete and memorable.

Example: Before launching a new product, imagine it’s one year later and the product has flopped. What happened? Perhaps you realize the product might be too complicated for users, the price point could be wrong, or distribution channels might be inadequate. Now you can address these issues before they occur.

Technique 2: The Stoic Negative Visualization

Inspired by ancient Stoic philosophy, this technique involves deliberately visualizing worst-case scenarios to: - Reduce anxiety about potential negative outcomes - Increase appreciation for what you already have - Prepare contingency plans for genuine risks

Example: If you’re worried about a presentation, visualize specific things that could go wrong (technology failing, difficult questions, etc.) and how you would handle each situation. This reduces anxiety and improves preparation.

Technique 3: The “Not To-Do” List

Instead of focusing only on what you should do, create a list of things you commit to not doing: - Behaviours that waste time or resources - Common mistakes in your field - Actions that violate your principles or values

Example: A “not to-do” list for a writer might include: “Don’t check email before writing 500 words,” “Don’t edit while drafting,” and “Don’t compare my first draft to others’ published work.”

Technique 4: Inversion Brainstorming

This group technique flips traditional brainstorming on its head: 1. Start by asking how to achieve the opposite of your goal 2. Generate as many ideas as possible 3. Then invert each idea to create potential solutions to your original problem

Example: If your goal is to improve team communication, first brainstorm “How could we make team communication as poor as possible?” (Ideas might include: withhold information, use confusing jargon, have no regular meetings). Then invert each idea for potential solutions.

Inversion in Action: Real-World Examples

Example 1: Jeff Bezos and Regret Minimization

When deciding whether to start Amazon, Jeff Bezos used a form of inversion he calls the “regret minimization framework.” Instead of asking “What should I do?” he asked “What decision will I least regret when I’m 80?” By inverting the question to focus on minimizing future regret rather than maximizing immediate gain, he made a decision that changed his life—and the retail world.

Example 2: Warren Buffett’s Investment Strategy

Buffett famously focuses on avoiding losses rather than maximizing gains. His first rule of investing is “Never lose money,” and his second rule is “Never forget rule number 1.” This inverted approach has helped him avoid the spectacular losses that have derailed many investors chasing maximum returns.

Example 3: Designing for Accessibility

When Microsoft developed the Xbox Adaptive Controller, they inverted the typical approach to game controller design. Instead of asking “How do we make a controller that works for most people?” they asked “What prevents people with limited mobility from using standard controllers?” This inverted question led to an innovative design that opened gaming to a previously excluded audience.

Practical Exercise: Your First Inversion Analysis

Let’s practice with a common challenge: improving productivity.

1. Forward Approach: “How can I get more done each day?”
2. Inversion Approach: “How could I guarantee that I get as little done as possible each day?” Possible answers:
• Start the day without any plan
• Constantly switch between unrelated tasks
• Respond immediately to every notification
• Work when I’m most tired
• Tackle the easiest, least important tasks first
• Keep my workspace cluttered and disorganized
• Never take breaks, leading to burnout
3. Inverted Solutions:
• Begin each day with a clear plan
• Focus on one task at a time
• Batch process notifications at scheduled times
• Align difficult tasks with my peak energy periods
• Prioritize important tasks, even if they’re challenging
• Maintain an organized workspace
• Take strategic breaks to maintain energy and focus

Notice how this approach reveals practical solutions that might not have emerged from the forward question alone.

Try this with a challenge you’re currently facing. What would guarantee failure? Once you have that list, how can you do the opposite?

When Inversion Works Best (and When It Doesn’t)

Inversion is particularly effective for:

• Complex problems with many variables
• Situations where avoiding failure is more important than maximizing success
• Challenges where conventional approaches have failed
• Planning processes where overlooking potential obstacles could be costly

However, inversion has limitations:

• It can sometimes lead to overly cautious thinking if not balanced with forward approaches
• For truly novel situations, it may be difficult to imagine what would cause failure
• It works best as part of a broader toolkit, not as your only approach

Integrating Inversion into Your Problem-Solving Process

To make inversion a regular part of your thinking:

• Ask inverting questions routinely: “What would make this worse?” “How could this fail?” “What am I trying to avoid?”
• Schedule pre-mortems for important projects and decisions
• Create “not to-do” lists alongside your to-do lists
• Practice negative visualization for situations that cause anxiety
• Combine inversion with first principles thinking by questioning assumptions about what would cause failure

Conclusion: The Counterintuitive Path to Better Solutions

Inversion might feel unnatural at first—our minds naturally gravitate toward thinking about what we want rather than what we don’t want. But with practice, this counterintuitive approach becomes a powerful tool for seeing problems from new angles and finding solutions that others miss.

By deliberately considering what would cause failure, you not only protect yourself from avoidable mistakes but often discover the hidden path to success. As the ancient Stoics knew, sometimes the best way forward is to first look backward.

In our next lesson, we’ll explore lateral thinking techniques that will further expand your creative problem-solving toolkit, helping you generate truly innovative solutions by breaking established patterns of thought.

Reflection Question: Think about a goal you’re currently pursuing. What are three specific actions or conditions that would virtually guarantee your failure to achieve this goal? How might avoiding these lead you to a more effective approach?