In the world of investing, a typical question an investor will ask is, "How can I make more money?" While this forward-looking optimism is the engine behind many investment strategies, it's also akin to building a house without considering the foundation. Instead, what if we asked a different question: "How can I avoid losing money?" This inversion in thinking isn't just a play on words—it's a fundamental shift in thinking that can lead to more robust and resilient investment strategies.

June 4, 2026
In the world of investing, a typical question an investor will ask is, "How can I make more money?" While this forward-looking optimism is the engine behind many investment strategies, it's also akin to building a house without considering the foundation. Instead, what if we asked a different question: "How can I avoid losing money?" This inversion in thinking isn't just a play on words—it's a fundamental shift in thinking that can lead to more robust and resilient investment strategies.
The concept of inversion—looking at problems backward or from an opposite perspective—is not new. The inversion framework was popularized by the Charlie Munger – Warren Buffet’s longtime business partner. It has been used effectively in multiple fields such as engineering, military strategy and chess, and can be applied in infinite ways. In investing, the inversion approach requires us to focus on minimizing losses rather than maximizing gains. It's about preparing for the worst while hoping for the best, which can lead to safer, more secure long-term investment decisions.
Investing with an eye toward what can go wrong might seem pessimistic, but it aligns well with human psychology. We are generally more sensitive to losses than to gains, a behavioral economic concept known as loss aversion. Daniel Kahneman and Amos Tversky, both behavioral economists, made this loss aversion concept mainstream. Through various research and testing, they came to realize that, for investors, the pain of losing is psychologically about twice as powerful as the pleasure of gaining. So, making decisions based on avoiding risk will naturally allow human nature to assist in this inversion framework.
While the traditional approach to investing will always have its place, the inversion principle offers a complementary perspective that can enhance an investor’s toolkit. By concentrating on how much we can afford to lose rather than how much we might earn, we cultivate investment strategies that are wise during economic downturns but are also structured to seize opportunities without risking the foundation of our investment portfolio. In the realm of investing, sometimes the best way to move forward is to think backwards.