The Importance of Questions + My Question List

“What you seek is seeking you.”

Rumi (1207 – 1273)

Sometime after college, I was exposed to the idea that…

Questions are extremely powerful.

In his book, Tribe of Mentors, Tim Ferriss says that the answers to anything and everything that we want is in other people’s heads and questions are our pickaxes. He attributes his 10x, 100x, and 1000x gains to his development of better questions.

I instantly fell in love with this idea. Not because I immediately recognized how useful that perspective is (although I wish I could say that), but because I was having trouble finding answers to the questions that were burning inside of me.

Why am I always getting the short end of the stick?

How come I’m not being rewarded for doing the right thing?

Is this all there is to life?

Will it ever get easier?

What’s the point of understanding complicated things if no one cares about them?

When will I have sacrificed enough?

How do I make more money?

Why do I keep making bad choices?

The frustration drove me deeper and deeper into nihilism, but this new piece of knowledge was bright enough to help me see the light.

It’s not that life was giving me harsh answers to my questions, it’s that I wasn’t asking the right questions at all. Then I realized…

Improve my questions, improve my life.

It’s not that knowing that asking better questions suddenly made my life better, but knowing that there is something I could do to give me a fighting chance was liberating and empowering.

I just needed to ask better questions.

Little did I know that the best was yet to come, and I was just beginning to understand the power of questions. There was another way to use questions powerfully.

This other idea was clearly articulated to me by Jordan Peterson, but I found it to be true in many other instances of my life.

When we’re asked questions, our minds almost immediately go to work on finding an answer.

This can be extremely uncomfortable if we’re asked the wrong (or right) questions. We can ignore the answers and act as if we don’t know them, but we will. The curse of knowledge is that we will never unknow something, so once we are asked the question we are also given the answer.

The cool part is that it doesn’t matter who asks the questions. We just need to be asked the question in order to start looking for an answer. This means that we can ask ourselves these questions or find someone to ask them to us.

At first, this idea seemed inconsequential but then I realized that I can discover honest and reasonable answers if I take a little bit of time to be asked what I really think I should do.

It can be something as small as “What do I want to eat for dinner?” or something as big as “What do I want my life to mean when everything is said and done?” Our minds will find us an answer if we let it.

This can be done in a way that is ineffective, but the key is to want to answer the question in a way that does not compromise ourselves. Try to be genuinely curious about the answers.

Suddenly, big questions don’t worry me as much and smaller questions are answered with myself in mind. My major life choices aren’t made carelessly or for other people. Learning and practicing this is so freeing.

Despite my question list being presented in no particular order, I do think it’s important to mention that good questions in the wrong order can get bad responses. Sometimes jumping right to the deep work questions can surface some superficial answers. If we take the time to warm people up with easier questions before jumping right into the difficult stuff, we’ll get answers that are more honest and well thought out.

My Question List

Here is a list of every question that I’ve found worthwhile to ask myself. I recommend spending at least 5 minutes thinking about each one (obviously in your own time, there are way too many of them to do it all at once). A lot of these questions aren’t necessarily designed to give me pragmatic answers, but to get me to think differently and break old ways of thinking.

I think everyone should keep a question list, if you decide to make one please share it with me at chris@chrismukiibi.com. I would love to see what other people’s pickaxes look like.

Bolded questions are the ones that I would argue have most impacted my life.

“Often, all that stands between you and what you want is a better set of questions.”

Tim Ferriss (Tribe of Mentors)

In no particular order:

Like my Must-Read Book List, and many of us, this list is always in a state of becoming.

Every so often I’ll update this list with any new, and worthwhile questions I come across in my journey.