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The rise of the insight hunter

How developing curiosity changes the way you see the world

How many of you are familiar with the story of Christopher Columbus? The tale is that he departed Europe and headed west in the hope of reaching the East Indies to establish an alternative trade route. Instead he reached what we now know as the Bahamas and Central America and is widely credited with their “discovery” (although a Norse explorer named Leif Ericson actually landed in North America nearly 500 years before Columbus).

Columbus’ curiosity meant that a whole new world was “discovered” and it radically changed our understanding of the earth’s geography and its inhabitants.

The best way to develop curiosity is to start asking “why” a lot more. Ask “why” about everything.

Start by being curious about the small things that you encounter and work your way up to the bigger challenges.

Learn LIKE a child

“Mummy, why is the sky blue?”

“Daddy, why can’t I play outside?”

“Teacher, why do we have to learn maths?”

Have you ever noticed that children ask a lot of questions? If you are a parent, I’m sure that you have experienced the frustration of answering a question from a child, only for it to be followed up with another “why”.

Have you ever noticed how we tend to ask less “why” questions as we get older? The simple answer is that as we get older we acquire more knowledge and therefore have less of a need to ask so many questions.

We already know some of the answers, and start to take things for granted by relying heavily on our assumptions. This can be useful in certain situations as it allows our brains to run on idle mode.

Thinking hard about things requires an enormous amount of energy so our brains use assumptions to create shortcuts in our thinking. Unfortunately, these shortcuts also encourage us to be lazy and to accept situations and beliefs as “the truth”. We stop being curious about things and almost work on autopilot.

We stop challenging “accepted truths” and assumptions and thus allow them to control our lives, even if upon inspection they don’t really make sense.

One very simple example of this in Malaysia is when we fill out forms we are often asked to provide our IC (identity card) number, date of birth, and gender. However, our IC number actually contains both our date of birth and our gender. So why are we asked to provide the same information twice in the same form?

Why ask ‘Why’?

Asking “why” helps you understand people, processes and problems. It’s only when you start asking “why” and seeking out the answers that you are able to develop insights.

This means that you have developed a deep understanding about something (or someone) and have seen something that maybe nobody has noticed before, but could be important.

Sometimes these insights appear to be obvious, but remember because we are running on autopilot most of the time it becomes easy to gloss over things that should be obvious.

This is called “insight hunting” and the main weapon for an insight hunter is the question “why?”

When you start asking “why” you start to understand why things are the way that they are. Then you can start challenging these accepted truths and develop new ideas and innovations.

How to become a great insight hunter?

Unfortunately there are no shortcuts. Insight hunting is a skill and it can be enhanced just like any other skill.

It takes practice to become an effective insight hunter. At the beginning we tend to only see the superficial insights. As we practise, we start to see more and more.

For example, when we are learning a new language we only know a few basic
words and we struggle to understand much of what is being said. Then as we progress we learn more words and phrases, and we are able to piece together a conversation even if we don’t understand everything that is being said. It’s the same with insight hunting: at the beginning you may not see a lot of insights, but with practice your vision will improve and you will start seeing insights everywhere.

As with any skill some people will find it easier to pick up and develop while others will struggle, especially at the beginning. Don’t give up. Keep asking “why” and trying to understand why things are the way they are, and then challenge this. A great piece of advice to help you develop your insight hunting skill is to keep a “surprise journal”.

Julia Galef, the president of the Center for Applied Rationality, supports the need to practise being curious. She keeps a surprise journal because she says, “You see more surprising things when you are looking for them.”

Be a Curious Cat


If people weren’t curious and didn’t challenge and question things by asking “why”, we would live in a very different world. Being curious can be risky, it often leads to uncharted waters. However the potential rewards are huge.

Even if you don’t discover what you expected to discover, you still gain some new knowledge, and in the case of Columbus you may even discover something greater than you intended.

So go out there, be curious, ask questions and challenge assumptions. Who knows what you may discover.

This article originally appeared in The Star Newspaper on 24 January 2015.

Please visit www.findhiong.com to learn more about me.

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