How Inverting Problems Can Unlock Smarter Solutions

Posted by Nick DeGregorio on January 29, 2025 at 8:00 AM

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When you’re faced with a problem, your first instinct is usually to look for solutions. You map out goals, brainstorm next steps, and focus on the outcome you want. But what if the real key to solving a problem lies in flipping it on its head? What if, instead of thinking about what you want, you focused on what you absolutely don’t want? This simple yet powerful approach is called inversion, and it’s one of the most underrated tools for rational thinking.

How Inverting Problems Can Unlock Smarter Solutions

Inversion isn’t about complicating a problem. It’s about seeing it from a different angle. If you’re stuck, the easiest way forward may be to ask: “How can I make things worse?” It sounds counterintuitive, but that’s the point. By identifying what could go wrong, you can create a clear roadmap to avoid those outcomes. The problems you don’t want suddenly become the foundation for the solutions you do need.

Let’s say someone asked you to improve the economy of a country like India. A typical approach might involve brainstorming ways to boost GDP, increase trade, or strengthen infrastructure. But with inversion, you’d ask: “If I wanted to ruin India, what would I do?” You’d probably point to things like corruption, poor education systems, crumbling roads, or mismanagement of resources. From there, you flip it back, now you know what to avoid and where to focus your energy.

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This mental trick works because it removes the noise that comes with ambition. When you think only about what you want, it’s easy to get lost in ideas that sound good but don’t actually matter. By narrowing your focus to what you want to avoid, you cut straight to the core issues. You’re forced to confront the threats, weaknesses, and blind spots you might otherwise ignore.

Inversion is also practical. It works in everything from personal decisions to billion-dollar businesses. Want to build a successful company? Instead of asking how to succeed, ask: “What would cause this business to fail?” You might identify poor cash flow, a toxic culture, or bad hires as major risks. Once you know what could destroy the company, you can design systems to prevent those outcomes.

The beauty of inversion is its flexibility. It’s not limited to fixing problems; it works for setting goals, too. If you want to be healthier, don’t just focus on hitting the gym or eating salad. Ask: “What would make me less healthy?” Skipping sleep, drinking too much, or eating processed foods might top your list. By identifying those habits and avoiding them, you’re already moving toward your goal.

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This “back and forth” way of thinking, flipping between what you want and what you want to avoid, keeps you balanced. It’s not about being pessimistic; it’s about being clear. Goals are important, but they’re only half the picture. The other half is the mess you want to avoid, and ignoring that mess won’t make it disappear.

The best thinkers use inversion all the time, even if they don’t call it that. It’s a tool for clarity, precision, and better decisions. If you’re a leader, inversion helps you cut through complexity and focus on what really matters. If you’re an entrepreneur, it saves you from chasing shiny ideas while ignoring the pitfalls that could sink you.

But inversion isn’t just for the big moments. It’s something you can practice every day. Struggling to manage your time? Instead of asking how to be more productive, ask: “What wastes my time the most?” Tired of toxic relationships? Don’t ask what makes a great friend; ask what makes a terrible one and avoid those traits.

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The more you use inversion, the more natural it becomes. You start seeing problems differently. You think more rationally. And you learn to avoid the unnecessary pain that comes from chasing the wrong solutions. In a world where everyone is rushing to fix problems head-on, inversion helps you sidestep mistakes altogether.

At its core, inversion is a simple mindset shift. It’s about asking smarter questions, so you can get to smarter answers. By thinking about what to avoid, you protect yourself, your team, and your goals from unnecessary failure. You might still face obstacles, that’s life, but you’ll have a clearer, calmer strategy to tackle them.

The next time you’re stuck, don’t just look for the right answer. Flip the problem. Ask what could make it worse, and then work backward. You’ll be surprised at how quickly the solutions start falling into place.


 

Topics: CEO Roundtable, CEO Roundtable - Leadership