What I Learned by Asking 100 Questions in 100(ish) days

Several months ago, I shared a video with our high school students telling them that the most important life skill they could learn was the art of asking.

I’ve spent the past 100(ish) days testing this advice out. I decided several months ago that each day I would post one question to my Instagram (kkaldous) and I would spend a few minutes thinking about the question and how it might apply to my own life. When I began, my intent was to go until I ran out of questions. It’s now been 100 days and I have a backlog of questions I still haven’t posted yet, so I’ll keep going till the well runs dry.

Here are a few things I’ve learned during this experiment so far….

?? We ignore periods and pause at question marks

The concept is so simple that you may have already stopped reading this explanation because you moved onto the next bullet point. But think about how our brains are wired. You can tune out anything that ends with a period. But what happens when you spot a question mark? You stop. You stop because the question has created an open loop that somehow needs to be closed. This is true when someone is speaking to you and it is just as true when you’re speaking to yourself. We need question marks. They force us to pause and try to close the loop. Over the past 100 questions, each time I saw the question mark, I stopped and was forced to wrestle with what it might look like to close the loop. These pockets of time are priceless because they train you to think differently.

?? Not many questions come with one right answer

There were many times during the past 100 days where I shared my current thinking on a question and then realized after reading the comments that there were a variety of ways to answer the question and often I didn’t have the best answer. While it’s good to take time to ponder on your own questions, it’s also smart to open up certain questions to the ‘believable’ people in your life. 

?? Questions (may) improve decision-making

There’s an assumption that the act of asking will improve the final decision. The equation is not as simple as “asking = better decisions.” It’s more complex because life is more complex. There are often many roads to the solution you’re seeking. Different questions will take you different places. Sometimes you need to be focused on the micro and if your questions are too macro you won’t arrive at the best conclusion. Over the past 100 questions I’ve seen how certain questions have popped back into my mind days or weeks later because they felt like the right variable to insert into the equation. The more questions you have access to, the more variables you have to work with when trying to solve for evolving equations.

?? You’re allowed to change your answers

In 100 days, I have already seen my answers change for several questions. Sometimes we think we can’t change our opinion on issues because it makes us look indecisive or weak. As I saw answers from other people to different questions I realized there are so many different ways to approach some of these issues and there is no problem with updating your opinion based on new information. In fact, I think that’s been one of my favorite things about this experiment. As I have seen other answers pop up, I feel like I’ve arrived at better answers than when I just went with whatever I came up with on my own.

After 100 days, I'm convinced that practicing the skill of asking ourselves questions is more important than ever. It's changing the way I approach everything from relationships to decision making and has just generally made me more thoughtful. I'm excited to keep this experiment going.