In 300 BCE, the Ancient Greek philosopher Zeno founded a school of thought called Stoicism. Based on the practice of virtues and the acceptance of consequences, Stoicism flourished in Ancient Greece and Rome, becoming a widespread doctrine. One of the most influential theories of Stoicism was the method of inverse thinking, a problem-solving technique based on foresight.
The Stoics believed that by imagining the worst-case scenario when faced with a problem, they could create better plans to prevent its fruition. While most focus on achieving success through reactive problem-solving, the Stoics considered how they would manage failure. By doing so, they believed this could cultivate resilience whilst minimising adversities. This method of preparing for the worst was known as premeditatio malorum, which translates as the premeditation of evils. As a result of its popularity, inverse thinking not just in personal life but also in governance, military strategy, and philosophical teachings. By accepting that certain things were beyond their control, such as fate, the actions of others, or natural events, they focused their energy on what they could control: their reactions, decisions, and attitudes.
In life, we all encounter challenges, uncertainties, and setbacks. While many strive to achieve success and focus on the best possible outcomes, these individuals practised the opposite. Rather than simply using a reactive response, Stoics prepare for every possible negative consequence in advance.
For example, imagine a startup founder launching a new product. Instead of only focusing on the potential success, the founder practices inversion. They ask themselves: “How could I sell the fewest products possible?” This counterintuitive approach leads to insights that might otherwise be overlooked. For instance, they might consider neglecting customer feedback, using poor materials, underinvesting in marketing, or setting incorrect pricing as the best means to fail. As a result, our founder knows the exact factors that need adamant attention to lead to success. While this may sound like an obvious method of critical thinking, especially due to its generalisability, it is a skill many people lack.
Take one of your recent issues as a direct method of testing. Maybe you have recently taken up a new financial plan for retirement. Instead of assuming everything will go smoothly, try considering the worst-case scenarios. For instance, start by asking yourself “How do I increase the possibility of losing my whole retirement fund?” Well, for that you would want the stock market to crash, unexpected medical expenses, and high inflation. So, as you now know the biggest risks, you know the best mitigations (diversifying assets, comprehensive healthcare, inflation-protected securities, and annuities).
Not only does this method of thinking reduce your risk of failure, but it also significantly enhances your resilience and adaptability. When you’ve already considered every worst-case scenario and have contingency plans in place, you’re less likely to be disappointed or caught off-guard. Furthermore, inversion helps you identify potential blind spots in your planning. When you think about how things could go wrong, you might uncover risks or weaknesses that weren’t immediately apparent. As a result, leading you to confront uncomfortable possibilities that ignorance could otherwise ruin.
I can’t understate the impact this critical thinking skill could have on your daily decision-making. As it is generalisable to almost all decisions, it becomes vital to perfect. Whether you’re considering a career change, purchasing a new home, or even making daily choices about how to spend your time, applying this method of inversion can become incredibly powerful.
By deliberately asking yourself the best way to fail, you become more aware of potential risks and can take proactive measures to mitigate them, leading to a much more secure and aware life.