The importance of "stupid" questions

I don't think people ask enough stupid questions, where a stupid question is one that challenges a core underlying assumption in the situation. For example, if people were arguing over how to put a fire out, one stupid question would be "why do we need to put the fire out in the first place?". This question might seem fairly stupid, but note that in the case of controlled forest fires, someone had to ask this before we began intentionally starting forest fires.

From what I've seen at work, people seem hesitant to ask stupid questions because they are afraid of being perceived as stupid by others. Ironically, I've observed that those seen as the smartest by others are in fact the ones who ask the highest frequency of stupid questions. Questions like "why are we doing this in the first place?" or "can you explain why we're doing X instead of Y?"

Taking this even further, I've found that there's value in asking stupid questions in my own life. Simple questions like "why am I doing X everyday?" or "why do I even work at this job?" can act as a forcing function to revisit core assumptions about what makes us happy (or unhappy) in our daily lives.

There's a pertinent fable on this topic:

An American investment banker was at the pier of a small coastal Mexican village when a small boat with just one fisherman docked. Inside the small boat were several large yellowfin tuna. The American complimented the fisherman on the quality of his fish and asked how long it took to catch them.

The fisherman replied, “only a little while.”

The American then asked why didn’t he stay out longer and catch more fish?

The fisherman said he had enough to support his family’s immediate needs.

The American then asked, “but what do you do with the rest of your time?”

The fisherman said, “I sleep late, fish a little, play with my children, take siestas with my wife, Maria, and stroll into the village each evening where I sip wine, and play guitar with my friends. I have a full and busy life.”

The American scoffed. “I have an MBA from Harvard, and can help you,” he said. “You should spend more time fishing, and with the proceeds, buy a bigger boat. With the proceeds from the bigger boat, you could buy several boats, and eventually you would have a fleet of fishing boats. Instead of selling your catch to a middle-man, you could sell directly to the processor, eventually opening up your own cannery. You could control the product, processing, and distribution,” he said. “Of course, you would need to leave this small coastal fishing village and move to Mexico City, then Los Angeles, and eventually to New York City, where you will run your expanding enterprise.”

The fisherman asked, “But, how long will this all take?”

To which the American replied, “Oh, 15 to 20 years or so.”

“But what then?” asked the fisherman.

The American laughed and said, “That’s the best part. When the time was right, you would announce an IPO, and sell your company stock to the public and become very rich. You would make millions!”

“Millions – then what?”

The American said, “Then you could retire. Move to a small coastal fishing village where you could sleep late, fish a little, play with your kids, take siestas with your wife, and stroll to the village in the evenings where you could sip wine and play guitar with your friends.”

It's been scary to see how fast time has gone by since graduation. Asking stupid questions has helped me to focus on what's important, both at work and in my broader life.