More To That

An illustrated, long-form blog that delves deeper into the things that make us who we are.

The Questioning Mind Is Most Alive

Today I want to talk about the art of listening, and how asking questions is the gateway to understanding.

Growing up, it was easier for me to address groups of people than it was to chat with someone 1-on-1. For example, throughout my college years, it was quite natural for me to tell a story to a table of friends, but the thought of hanging out with someone by themselves made me nervous. This was an issue that baffled many of my friends, given that public speaking is a more common fear than anything that could accompany a casual 1-on-1 hangout.

Well, around my late-20s, I recall making a conscious effort to figure out what was going on. I thought about why I had this fear of chatting with a single person, and I realized that it had to do with the specificity of the interaction, and the pressure that resulted from having such a directed focus. That might sound a bit confusing, so I’ll take a moment to explain.

The way I saw it, when I was talking to a group of people, I didn’t need to think about any single person in particular. In essence, I was sharing my thoughts with a big blob of people, so I didn’t have to consider how any one person might respond to what I was saying. It felt more like a broadcast than a conversation, and the nature of that interaction would generally be guided by me, the broadcaster.

But when I was chatting with a person 1-on-1, I was forced to take off that broadcaster hat and put on my conversation one. Everything I spoke about had to fit within the context of the person’s personal experiences, or else the interaction would be awkward and uncomfortable. I could no longer get away with making broad generalizations and telling a bunch of stories that may have no relevance to the person in front of me. Everything I said would be accompanied by a specific response, whether it’s through the person’s words, their body language, or their facial expressions. And trying to keep inventory of all their responses while formulating my own seemed like a daunting task.

What I quickly realized, however, was that this issue stemmed from my relationship with control.

I felt comfortable with talking to larger groups of people because I felt like I had control over the interaction. I was orchestrating the way things ebbed and flowed, and I didn’t have to have to personalize anything or cater to any specific experience. It was a one-way current that I had agency over, and that felt liberating, in a sense.

Well, I quickly realized how problematic this was, and that things needed to change.

After all, what’s the point of conversation if you’re merely broadcasting your thoughts? What good is getting together with friends if you don’t seek to know them better? And furthermore, what good is being funny and entertaining if your friends don’t know who you truly are?

At this point, I decided to take a concerted effort to address my fear. I realized that this whole time, I was viewing conversation in a self-serving manner, and was missing what ultimately made it so beautiful. So rather than getting together with friends in small groups, I asked individual friends to hang out in a 1-on-1 setting instead.

At first, I have to admit… it was quite difficult. I noticed how conditioned my mind was to put on a performance of sorts, to always have something to say in order to avoid silence. I would always default to broadcaster mode, to try and say something insightful or funny that would shout, “Hey, I’m worthy of your attention!”

But over time, it dawned upon me how tiresome this was. Not only was it fatiguing, it was also pointless. Ultimately, there was nothing I needed to prove to the friend in front of me, nor was there any expectation to showcase the best of my abilities to them. The mere fact that we were sharing space together was enough, and everything else was about taking wherever our curiosities took us.

And it’s the last word – curiosity – that changed everything for me.

The great opportunity about being present with the person in front of you is that you can learn about them in a way that no group setting can offer. It’s just you, the person, and your desire to know more. We often reserve questions like, “What are you most curious about?” for strangers or small talk, but the reality is that they should be directed toward the people you (think you) know best. Chances are, there are so many interesting stories you’ve yet to hear from the people you’re closest to.

I started realizing that the more questions I asked, the more I learned. It seems like such an obvious statement, but it’s quite shocking how few questions you ask when you’re with people you’re comfortable with. (As an experiment, see what the dynamic is like the next time you’re having dinner with your family or close friends. There will likely be patches of silence or a flurry of statements, but rarely a steady stream of questions.) There are many reasons why this may be the case, but the most salient is that your curiosity toward the person has been extinguished.

Krishnamurti once said that a mind that doesn’t ask questions is one that is dead. I find this also applies to relationships as well. If you’re no longer curious to know about the person in front of you – be it your childhood friend or your father – then that relationship is devoid of life. You can say that you love someone, but if you no longer seek to inquire about that person’s heart and mind, then that love will fade into complacency and then into nothingness.

Once I understood just how powerful a question can be, I started making liberal use of them in my conversations with people. I found that it’s far more interesting to learn about the person in front of me than to share an amusing story about myself. If anything, the fastest way to learn about myself and the nature of my mind is to learn more about the nature of others. Once I internalized this, I understood just how precious each conversation can be.

Fast forward to today, and funnily enough, I’d say that I’m a bit more comfortable in a 1-on-1 setting than in group ones. But at the same time, I notice that it isn’t about how large or small a gathering is; what matters is how curious I can be about the people I’m sharing space with. And as long as questions are a prominent feature of that interaction, then there will be a great opportunity to tap into something special about our shared human nature.


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For more stories and reflections of this nature:

The River of Compassion

The Problem of What Others Think

The Staircase of the Self


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