I have struggled with writing this article for a long time. The ideas have been floating around in my head, I’ve written and re-written them, I’ve tried to stitch paragraphs together, to weave a narrative throughout, but making a coherent whole has still eluded me. After all its different forms, I feel some disappointment about this one, but it seems to be the best I can do for now. So, here is a collection of advice for my older self on the topic of conversation.
Silence is OK but not forever
I like going on walks with my wife. There’s something about fresh air, nature, and light activity that seems to invite great conversations. One day, on one of these nice walks, she remarked that she is often carrying a lot of the conversational burden. She’s right. I normally do a good job of keeping the conversation going, but once it reaches a natural end, the next conversation is not often started by me. I like silence, and I like being in silence together, with occasional remarks about our surrounding, but it’s lazy to let that be the norm forever.
At first, I worried that the reason I was silent was that I preferred my internal monologue to having a conversation with her (a disconcerting thought). Actually the real reason is not that shameful. These moments of silence arise from laziness, when I’m using the walk as a way to relax and process the day. In these moments, I’m not paying any particular attention to my train of thoughts. (There is something to be said about being absent but I won’t get too off-topic.) It’s fine to have these moments to relax, to let my mind wander without any focus. It’s fine to not find any of these thoughts worth spawning a conversation about. But as some point, effort must be made to create an interesting conversation.
This is the reason I’m writing this article: to have the tools to create interesting conversation, rather than relying on luck to stumble into them.
Spend more time thinking about interesting things
Being a good listener is important in conversations, but at some point, you have to bring some of yourself in there, otherwise your partner is just talking to themselves. My best conversations have been from talking about ideas that are on the edge of our understanding, conversations where we have to discover together, or when something is bothering me and I can have someone there to help me make sense of it. If I want to have more of these kinds of conversations, I need to spend more time being curious about ideas and spend more time with them.
I learned this while reflecting on the conversations I have with one of my best friends. Living with a 12h time difference means we don’t speak very often, but every time we do, the conversation lasts for hours without either of us noticing the time gone by. What I learnt from him is that it doesn’t have to be complicated. (I have a tendency to overcomplicate entry into bigger conversations, and thus never end up actually doing it). One idea or concept, and a simple question: “What do you think about X?” Then you can get curious and ask good questions to really dig deep and even go on tangents. This can last hours, especially if you’re both trying to get to the bottom of a question that doesn’t have a clear “correct” answer. Once you’ve done this with multiple people (as he often does), you can have them talk to each other in your head. You can understand them better because you now have to explain their ideas, and sometimes even argue for their position on a debate.
Sometimes I overhear other conversations and I become cynical about my individuality and self-conscious about the banality of the conversations I have with others. The same topics, the same angles, the same opinions, the same recycled sequence of words. I repeat what I read in the Economist, what I shamefully scroll through on Youtube, what I’ve heard from someone before who has also gathered it from their flawed sourcing system. There’s nothing wrong with exploring flawed positions with others, that’s how we learn, but how often have I been midway through a conversation and realised I’ve already had the exact same with three other people in the last year? The problem is I’m not spending enough time thinking about interesting things. I have the same surface-level algorithmically curated set of information as everyone else.
Instead of filling my attention in 60 second segments on entertainment with no long term value, I need to let myself be bored to fuel my curiosity and then give myself long stretches of time to think.
Interrupt!
Interrupting people is rude, you need to let them speak, it shows you care more about the sound of your own voice than—no. This piece of advice is a little bit tongue-in-cheek but if you want your conversation to be more than a single narrative with a few obligatory questions at the end, then you need to interrupt your storyteller. Stories are so much more interesting when they aren’t linear, when you can branch out and turn a 10 minute narrative into a two hour psychoanalysis session.
I recently finished a long holiday and moved to the other side of the world. When I see people now, they all seem curious to know how it went. The conversation that follows will live and die by the kinds of questions that are asked. By the time I’m talking to you, I have probably already told this story five times already. You may feel like you are being a diligent listener, but if you don’t ask any questions, I feel like my story isn’t interesting you and now you’ve forced me to keep you hostage with my boring story. If I try to speed up the story, it’s sure to be boring because it has no substance, and if I go into details, then I’m prolonging both of our sufferings.
That’s why I love being interrupted, if I can feel the interruptions come from interest and excitement about the story. I love telling stories to friends because in doing so I will discover something new about the story I lived. I get to experience it in a different way. On the listening side, it also makes it special: you get to find out a detail no one else knew about, you get to spend more time on the parts of the story you find interesting. Interruptions and questions turn a linear story into a rich conversation.
Next time a friend starts telling you a story, don’t let them get away with telling it from start to finish without them explaining how they felt, why they did that, or how others reacted. Don’t be afraid to stop people to clarify something. Don’t be afraid to steer the conversation away for a little bit. They have already repeated this story (probably close to word for word) to many people already. Let them enjoy this conversation by getting them to say something about it that they’ve never said before. Be the person that asks the one question that makes them reframe the entire story. Don’t be the person who interrupts to make it about themselves, or to relate. And don’t constantly interrupt — let them build the trunk of their story, just help with the branches every now and then.
Debate is not the only form of conversation
You would be forgiven for thinking that the only way you can have a lively conversation is to have disagreement. Conflict is the main narrative structure in almost everything we consume but it doesn’t have to be this way! You can have conversation where no one is arguing for a particular position or opinion, where instead, the driving force is curiosity. This is obviously the case with biographical conversations, but it can also be the case with conversations about ideas. It is possible to hold judgement while still being critical. I think Socratic dialogue is a great tool if everyone involved has the same goal of discovering the truth; however, most of the time (and it’s certainly the case in Plato’s writing), it is used as a debating tool to show that the other person really doesn’t know as much as they think (or say) they do. Even if you disagree with someone about something, that disagreement doesn’t need to become the focus of the conversation, instead you can try and discover exactly what the position is, and why the person has come to believe it. Conversation as a medium for curiosity and discovery is the best kind of conversation. Which leads me well into…
Conversation is how we build ourselves
Up to this present moment, you have been shaped by your genes and your environment, by your interactions and conversations with others. You have some self-concept of who you are as a person, or who you wish to be: values you aspire to, vices you wish to refrain from, aspects that you like about yourself, and aspects you dislike. Those qualities and faults are only manifested in the real world through your interactions with others; in other words, you do not exist outside of how you behave in the world. You are not kind unless you do kind things; you are impatient if you lose your temper while walking behind someone who is too slow. And so, naturally, there exists a divide between the person you think you are, and the person you actually are. By becoming aware of this gap, you adjust and construct yourself.
There is only so much you can find out about yourself through introspection. Yes, sometimes it takes time to find the right words, or the right way to frame something. Sometimes we have to explore different thoughts but after some time, we reach the end of our self-knowledge and we start going around in circles. There are only so many possible answers to “who am I”, and “what do I believe” before you get to a dead-end and the answers become repetitive, boring and obvious. What others have to say to those questions then becomes infinitely more interesting! We use the input from the conversations as fuel for our ideas, and we build ourselves.
Some people have a cynical view on the presentation of self, that it is a performance, or a mask, implying we use this presentation to disguise ourselves from others, or to behave in a way that shapes their reactions in self-serving ways. When I say we use conversation to build ourselves, I don’t mean that we use it to fabricate an outward appearance, I mean that we use it to build ourselves. A real conversation is one where you can be honest about the person who you believe you are.
And so, if a great conversation can be so self-affirming, or revelatory, it becomes one of the best gifts we can offer our loved ones. When we ask them questions, when we are curious about them, we let them create themselves. We let them challenge our assumptions and biases we hold about them. When we become aware of these, we should try and challenge them through conversation. People can’t fit neatly in our head, their world is as rich as yours is.
How can you say you know someone if you haven’t challenged your assumptions about them? Why not throw them a curveball to see how they respond? Why not invite them to spend time in a different context? Why not try find out more about a person?
Good conversations are sometimes boring conversations
The worst kinds of conversations are a silly dance. I choreograph my words so you can respond with the right words in the right order, so I can say the exact thing you expect me to say, and so on, until we get to the end of the script and then make an awkward exit. Sometimes though, we need a little ritual like that to get into it. There is actually a surprising amount of information you can gather about someone from such a banal interaction. (Whether it is their curated persona, or in fact the whole person). Their word choice, their facial expressions, and their pacing will tell you about the kind of person they are: do they have a penchant for humour, are they confident, are they anxious, are they reserved? It goes against all I’ve talked about self-actualisation through conversation, but you can very quickly put people in boxes from these theatrical displays. But once they’re over, you can decide if there is something to further pursue, or if you should just move on with your time.
Sometimes you need to have many of those theatres before you can get to somewhere substantive. Some people don’t let a lot of themselves out at once, and it takes more work to get them comfortable sharing themselves with you. Sometimes what you need is time and familiarity. And the more commonplace conversations you have, the more opportunities you have for picking the most interesting path of conversation.
There is also something comforting about repeats. Reminiscing about shared experiences with friends is fun — it’s not new, it doesn’t come with any self-discovery, and it doesn’t even necessarily have any meaning after the fact — but it’s time spent together, having fun. If you had to explain the conversation after the fact, it would be boring, but in the moment, there is nothing else you’d rather do. Time spent with others talking about nothing is better than time spent on your own constantly distracted.
Recap
- You don’t need to feel bad for not filling every silent moment, but you can’t get complacent about putting effort into conversation.
- To have good conversations you need to have a rich intellectual life. Read, write, look at paintings, listen to music, and keep a log of interesting questions or topics you want to discuss with people.
- Don’t just listen, help shape the conversation by asking tangential questions. Don’t make it about yourself, and remember to bring it back to the main topic.
- Hold judgement, don’t always treat a statement as something to be argued with. Conflict is not the only form of conversation.
- Become aware of the categories you put yourself and others in, and have the curiosity and generosity to try and break those.
- Not every conversation has to be meaning-making; there is no need to put extra pressure on every conversation.
Header Image
Lunchtime at the Building Site on the Van Diemenstraat in Amsterdam, George Hendrik Breitner (link)