good conversations have emergent properties

or: people have very vivid interiorities

Black Cradle of Bright Life, Vangel Naumovski

Conversations have emergent properties: products co-created by two people. Distinctive behaviors, shared taxonomies, even entire secret worlds.

I find great joy in discovering something fundamental about another person through dialogue. How do you model the world in your head? How do you navigate the precipice or terrain between ideas? How do you skate across the surface of this world? When I first met you I knew we’d be close. Or could be. Our first conversations had an inevitable gravity to them.

In many ways I think J taught me what conversations could be. Or it was something we taught each other. J and I met properly in the grass square outside our first year shared dorm in college. Two young girls with big suitcases, fearful and excitable about change. We awkwardly exchanged numbers clutching our freshman flyers and moving carts. At some point on that first day, something clicked.

We proceeded to talk nonstop for the next 4 years.

A shared artifact: we wrote a newsletter together for a year on a (then) new and novel platform called ‘Substack’, tracking our live conversations. All our weird obsessions, on loneliness, love, music, writing — Maggie Nelson, Hannah Arendt, Jenny Odell, Pico Iyer, Dostoyevsky, John Williams, Italo Calvino. We stood in the kitchen sometimes and discussed Johns and Rauschenberg and our eccentric art history professor who cried when she looked at a specific sculpture. Those conversations formed their own history. Had their own escape velocity. I still feel their implications today.

From an excerpt from Irish poet, theologian and philosopher John O'Donohue's conversation with Krista Tippet of On Being (thank you Brian):

When was the last time you had a great conversation? A conversation that wasn’t just two intersecting monologues, but when you overheard yourself saying things you never knew you knew, that you heard yourself receiving from somebody words that found places within you that you thought you had lost?

This search for aliveness in dialogue with others is central to the search of any human’s life. It is more than just language. It’s the search for a moment of being truly seen and understood. At the same time, excavating something out of yourself that you didn’t even know was there.

What I’ve been feeling recently: we have the agency to make conversations better. For most people, self-expression through conversation is hard. It’s hard to make conversations feel safe and sacred. It takes effort to be attentive and involved. But that difficulty isn’t insurmountable, and it’s a shame to think of it as such. There is great loneliness inherent to being human. It takes great imagination and faith to believe in the alternative: that every conversation represents an open door. A possibility.

Here is Part 1 of some of my (non-complete) observations on what makes for better conversations:

Playful, radical presence

There are two main roles in a 2-party conversation: an instigator and a responder. Both are important and one should ideally occupy both roles within a conversation at different points in time. Two responders end up simmering in silence; Two instigators sometimes end up talking over each other. The beauty is the middle ground of awareness: instigate, reflect, respond.

Finding the balance between the two requires one to be deeply present. Being present is a craft, and sacred art form. When you are present you can tell when a conversation is being dominated or led by one party or the other, or body language shutting off or closing down. When you are present you pay more attention to what lights someone’s brain up, what paths to consequently follow. When people talk about something they love, their whole voice changes. Noticing this takes genuine involvement and participation in someone else’s state of mind.

It sounds like basic advice, but you’d be surprised how many conversations are incredibly transactional. Someone wants something from you, or you desire something from them. There’s no delight or play or intuition. I think the best conversationalists, and this extends to interviewers, are truly curious about the vivid interiority of another person. Where they seek inspiration from. What their neuroticisms are. What they’re captivated by. We’d be better served remembering that everyone has their own world, whole, beyond you — and a conversation the precipice to the rest of it.

Avoiding blocks and sinkholes

Blockages happen when there is information asymmetry between two people that prevents a conversation from functioning healthily. For example, if a dialogue veers into extremely technical topics, you might require a PhD or research background to continue the conversation meaningfully, or to even intuit how to unlock deeper ideas or lines of questioning. Sometimes these blocks can be mediated with thorough preparation on the person or topic prior to conversing with them, as is the case with well-researched podcasts or informational interviews.

Sinkholes happen when both parties aren’t certain of each others’ intentions or level of openness. By default, you sink into the same topics in fear of abstracting too far away from ‘safe pockets in conversation’. For example, sticking to strictly intellectual topics because you’re not sure how someone might respond to a question about their upbringing.

Either does a great disservice to the paths different types of conversations can take. My advice here is basically to be more aware of which one you’re getting sucked into.

If it’s a blockage from an external party, it’s best to acknowledge your lack of knowledge to change the topic or getting more comfortable asking base-level questions to level set (“Honestly, I’m not very familiar with X. What exactly does that mean?”). If it’s a sinkhole, I’d recommend testing the waters with new types of questions e.g., asking deeper questions about motivation, emotion, and state of mind (“What was an inflection point that changed your mind on something?”)

Creating new pathways through questions

It was a huge unlock for me when I realized you could direct the flow of exchange to new places and shapes. You just have to locate the right level or plane at which to engage another person — sometimes people want to meet you there. Sometimes not, but it’s a shame not to try.

Adam Mastroianni

articulated that good conversations unfold as a series of invitations from Good Conversations Have a Lot of Doorknobs:

When done well, both giving and taking create what psychologists call affordances: features of the environment that allow you to do something. Physical affordances are things like stairs and handles and benches. Conversational affordances are things like digressions and confessions and bold claims that beg for a rejoinder. Talking to another person is like rock climbing, except you are my rock wall and I am yours. If you reach up, I can grab onto your hand, and we can both hoist ourselves skyward. Maybe that’s why a really good conversation feels a little bit like floating.

What matters most, then, is not how much we give or take, but whether we offer and accept affordances.

It’s important to get to some degree of comfort with social risk in giving affordances. What I mean by this is taking the risk of asking more difficult, spontaneous, or direct questions that act as permission for someone to open up. To be more themselves. Often by doing so, you end up being more yourself too. How did the path fork after that moment? What do you regret? What’s the goal of your research: not the goal in 1 year, but the goal in 10? What does winning look like to you? How would you get to the answer if you don’t have one?

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Yesterday A and I sat in Washington Square Park and talked in the shade. We discussed that what we deem as our “legacy” can, in fact, be hyper-local and intimate. Maybe no one will ever know the details of what you’ve said and done to others, but its subtle or not so subtle effects on another person’s life is rewarding in itself. I sometimes feel that way about writing: it’s less of a mirror or loudspeaker, and more so an intimate conversation in a little corner of this world between you and me. If any piece means something for even one person reading, it would be enough.

There was a time in my life in recent past when I yearned for the types of conversations I am grateful to have today. What I was seeking was to feel at home in relation to others, to feel met on the same plane of thinking or emotional fabric. I was observing people carefully all the time and I found it deeply sad that it didn’t translate to being better with communicating with how I felt.

It’s gotten better over time in ways I can’t even articulate. Both a function of wider friendships and greater maturity. That might be the closest feeling to pure joy — when you realize what you’ve been searching for actually exists and was seeking you too.

Don’t get me wrong, I still have many bad or meh conversations on a daily basis. But I more frequently run into mind and heart-opening conversations that send me reeling.

Now, that is the magic that exists in a dance between two people. A dance that can’t be predicted or over-engineered, but slowly intuited over time. I wish we could’ve talked for far longer! I want to hear you say more. Kind of beautiful, right? That even one or two exchanges between the right people might alter the course of a life.

PS: Thank you for reading. If you do feel inclined; please like and share this post. Your support helps me reach more readers like you and build this community

PPS: I am planning a 2nd informal subscribers meet up soon, yay! (I held an official one late last year with a fantastic group). Stay tuned to my subscriber Substack chat if you’re interested as am keeping it small. I’m thinking we’ll just do a casual get together over drinks.