Going down the rabbit hole

As I enter the room and sit by the table that includes familiar faces from the conference, someone sitting next to me strikes up a conversation with a brilliant line that encompasses a question about the purpose of existence. I ignore the fact that we barely mentioned we recognize eachother and barely said our names, and dive into the discussion.

An hour of climbing down the rabbit hole is stopped when I feel surprised about having a great conversation with absolutely no intro. The best discussions begin in ways we usually don’t remember. Mostly they are short, but include some hints of what the conversation partner is more interested in. My surprise of how stark was the start of the discussion is calmed with “You look like someone with whom it’s easy to talk to and who’d enjoy philosophical discussions.”


Achievement unlocked.

May be a flirt, but hell. It’s all I’ve wanted to hear. Young me who had understood that communication is difficult and needs to be worked on, set a goal that she wants to become someone with whom it’s easy and interesting to talk to. Even now I still try to figure out how the hell do great conversations begin. It’s not always smooth or fast. Sometimes it needs some digging to be done.

Some people enjoy going down the rabbit hole, some people know very well what they enjoy discussing about.  They  are easy to talk to and easy to listen to, they direct the topic to more interesting questions. They, unfortunately, are in the minority. If good conversationalists are not around, you’ve got to take the lead and try to guide the topic to where thinking and listening becomes the ultimate pleasure.

How to do that? The first step is eliminating or accepting the fears you might have.

Approaching people is a big fear that possesses many of us. It almost feels the same as being on stage. Excruciating. “What do they think of me? Oh gawd, I’m making a complete fool out of myself! Soon they will realize how incompetent I am. Oh hell, how could I make this natural. Please, talk more, I have nothing to say!”

I used to be terrified of approaching people. As a kid, I was even terrified of people approaching me. Today, I find it hard to believe that that’s how I was. Having come out of it, perhaps the techniques I used could become handy to someone else as well.


The steps I used in my mind are ways of thinking that, having gone through many times, changed my mindset about a lot of things in communication. The fist thing that one should keep in mind or train is curiousity. Curousity killed the cat (read: the fear). It’s easy to kill and hard to instill, and curiousity makes communication genuine. It’s much harder to grow out of shydom when one has lost the inherent curiousity we are born with. Genuine curiousity is the basis of all interesting conversations.

At some point I realized I admired the people who dared to approach other people, the people who’d dared to share a compliment or strike a chat with a stranger. Having understood that most people share the same fears, I figured, if I’m afraid of approaching someone, but consider the one who dares to approach as brave, then the person I approach might as well think that I must be brave. Completing it with reading about that people in their death beds regretted most the things they had not done, and voilà!

The last one – that we regret things that we didn’t do – became the underlying motivation for most interactions. Soon it overtook other areas where fear had been plentiful.

A fear that some people could have, is the fear of being incompetent, saying meaningless or stupid things. To get through that, the only things that help are either gaining confidence in your knowledge or learning to listen. Reading more and training critical thinking are some basic ways to gain confidence in your knowledge.  Learning to listen would include loads of curiousity and willingness to learn. “Tell me exactly, what do you mean by that?” “So it means that…” “What if…”. Let the other person talk and you have to stress less of having nothing to say.

If you’re afraid of having nothing interesting to say, finding very interesting conversation partners is nearly impossible. Ask yourself, what do you want. Ask it a million times, Try to figure out the things you are passionate about, interested in or want to be better at. Once these are identified, just throw it out there.

In some cultures people believe that deep topics should not be discussed on chill time. So they bury themselves under football and topics popular in the media, not daring to throw their favourite questions on the table, even if they would love to discuss them instead. If you’re afraid that offering a question to the discussion out of the blue would feel awkward, fear no more. It will be awkward, but only for you. The rest of the people would either tackle the question and try to answer it, ask you why you want to know, or hint that they won’t be interested in discussing about it. To impose the topic properly, asking just once might not be sufficient. Most cases it would require explanations or extra questions that would help in digging, what is it that you exactly want to know.

If you are in a big group, asking one or two people at first makes more sense. Once they start talking, they attract other people from the group to be interested in what is being discussed about. In bigger groups, there’s always the fear that maybe other people won’t accept one’s interest in the suggested topic, so they dismiss it. If the interest is caught and someone actually has something meaningful to say, chances are, more people will be interested in hearing what that something is.

If the person you asked is not very interested, but is willing to listen, their involvement and your chances of getting deeper in meaningful topics depends on your passion and genuine interestedness. If you ask for the sake of asking, don’t bother. Ever. If the person won’t understand what you mean by your question, the conversation won’t get anywhere interesting – excuse your way out and stop wasting your time on coversations that teach you nothing.

Curiousity truly killed the cat, if the cat encompasses fears, boredom and boring people. Once two or more genuinely curious people meet, exciting, mind-explosive, thinkgastic conversations are born. If that’s what you’re searching for, don’t settle for any less.

Keep exploring.


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