I tend to ask a lot of questions. Sometimes it’s because I want to understand “why,” and sometimes it’s to confirm if the situation remains the same. However, people often get impatient with me, thinking that I’m trying to block their plans or wishes. They are accustomed to speaking indirectly and misusing “questions,” humanity’s greatest tool, as a subtle way to express their true desires. Nowadays, I ask more questions of myself—examining whether I am being stubborn or considering how my heroes might respond in the same situation.

I believe that maintaining mental and physical health is crucial, yet it’s challenging because we often don’t understand what we truly want. This can lead to pursuing socially accepted goals. While these pursuits may bring initial happiness, they often result in increasing dissatisfaction or even depression over the years. At that point, one might question whether the issue lies with the environment or with one’s own stubbornness or lack of resilience. It’s only through new setbacks and continuous reflection that we can discern what is toxic in the environment and what problems lie within ourselves.

My approach to asking questions typically revolves around: how to get from A to B, or how to choose between A and B. Charlie Munger’s approach to questioning is fundamentally different. Instead of asking what might lead to success, he focuses on what might lead to failure. As a result, Warren Buffett sometimes sees Munger, his older partner, as someone who often “throws cold water” on ideas, whereas Buffett considers himself the more approachable and lighthearted of the duo.

Mohnish Pabrai has shared several instances where he presented investment ideas to Munger, only to have them rejected within a minute. The most common reason? The proposed business was a “win-lose” model. Munger seeks businesses that are “win-win” or even “win-win-win.” This is why he rejects opportunities like Conwood Chewing Tobacco (which could cause cancer), Valeant Pharmaceuticals (which exploited patients by hiking drug prices), and TransDigm (which used monopoly pricing for airplane parts, potentially compromising safety). On the other hand, Munger admires Costco’s business model and has become both a board member and investor in the company. At its core, this reflects his consistent pursuit of his personal philosophy.

Great investors are both optimistic and pessimistic, but their perspectives often run counter to popular opinion. Since time and energy are limited, I find Munger’s critical “say no” mindset to be the most efficient approach when it comes to major strategic decisions. This is why Buffett calls Munger the “architect” of Berkshire Hathaway, while describing himself as the “builder.” Let’s not forget that Munger strongly emphasizes self-reliance and resilience—never indulging in self-pity. Once a decision is made, he advocates tackling challenges with unwavering determination, which reveals the optimistic side of his character.

“The best thing a human being can do is to help another human being know more.”

— Charlie Munger