Let's Catch Up - Thoughts On Conversations
What makes a great conversation? A friendship? A community?
The phrase “let’s catch up” is hardwired into our minds and mouths and lives. It conveys a startling breadth and depth of meaning. It’s how we say we miss someone, that we want to spend time with them, that we care about them and what’s happening in their lives, and much more.
This phrase also reveals a fundamental piece of our understanding of relationship and how to cultivate it well in our lives: It assumes knowledge of the events and happenings a person’s life is the same as intimacy with that person.
This assumption sets us on a hamster wheel. To be intimate with a person, I need know what’s going on in their life - but this, of course, is a moving target. What’s happening is constantly changing. So I need to keep up (“catch up”) with that person over and over if I am to remain intimate with them.
This sets the course for so many of our interactions (and insecurities). When we see someone, our desire for intimacy means we try to “catch up”. The starter pistol goes off, and we relate as much as we can of what’s happened recently, while they do the same. Because life and time are limited, we may even leave the interaction feeling like we haven’t fully even caught up - because, of course, we can never “fully” catch up.
Our communications are optimized for this “catch up” norm. The primary social networks of our lives (Facebook, Instagram, Snapchat, Tiktok) are not just focused on the visual (photos, videos) but are set up to give the impression that we’re “caught up” on the lives of people we follow. We get brought into the factual details and experiences via their stories. The systems are designed to produce content and then more content - so we’re always catching up (and thus always pulled back into the app).
I’m not quite blaming the social companies here - I think this happens as a mashup of culture and profit-seeking. Catching up or more factual sharing baked into the design of just about all of our communication mediums (text, email, etc.). We’ve optimized for speed, not thoughtfulness, and when things are moving fast, the superficial is all we have acecss to.
At a deeper level, this “catch up” instinct is a reflection of our how we conceive of our own lives. We define and identify ourselves primarily by what’s happening - the tangible, material realities of our lives. Put differently, knowing what’s happening in our lives is how we know ourselves, so it makes perfect sense to project this building block of our own consciousness outward.
But we all, I would hope, know this isn’t true deep down. And we also, I hope, have some relationships that transcend this understanding. People with whom we feel deep intimacy despite not knowing the specifics of their lives. People with whom “catching up” doesn’t mean trying to trade recent happenings but rather sharing with each other whatever bits of our Inner World are sparking with life. Exploring emotions, feeling the contours of new, co-created ideas, or simply being together in silence or spaciousness.
It might sound like I’m setting up this whole “catch up” thing to tear it down, to demonstrate why it’s wrong-headed and confused. And to be clear, I do think it’s one of the fundamental confusions of our culture (our individual and collective psychologies).
If you’re here, you may already share this view. Whether you study in Zen or simply have some inkling towards Eastern, mystical, or experiential spiritualities, you’re well aware that the sages and wise ones are fairly clear that our true identity is non-separate from all that is (and perhaps you’ve experienced moments of this). We’re all one or the Universe or fingernails on the body of God, or whatever your du jour expression of non-duality is.
But we live in this real world. We are part of this culture around us. It would actually be uninteresting if we all were permanently swimming in and fully in touch with non-duality. We would be off the hamster wheel of catching up (along with a bunch of other hamster wheels), but there wouldn’t be much to talk about.
The challenge is real intimacy within our lives - within our interactions, relationships, communities, and culture. There’s a wisdom and skill to this. How do I bring someone into my world as succinctly and deeply as I can in the relative, limited times I have with them. How do I hold space and offer questions and curiosities to another to allow them to bring me into their world?
Doing this means I need some of the practical details of your life. It means I need to share mine with you. But the trick, as I see it, is to use the “catching up” as a scaffold for going deeper (or more accurately, for cultivating intimacy in whatever form you want - intimacy doesn’t always mean depth, more on that shortly). The skill is sharing layers of experience and meaning simultaneously, in one move or one fell swoop, connecting what’s happening on the surface to what’s happening underneath (and offering someone else a conversational path to do the same).
It’s something like: This thing happened in my life, this is what it brings up, this is how it makes me feel, this is new territory I may be trodding on - and wow what is this new discovery that I (we?) might be making about my (our?) experiences, lives, foundational ideas, etc. Great conversations go down this path together, with questions and comments and shared sparks that serve as a shovel for the participants, allow us to dig deeper and ultimately explore together.
One more turning
But I want to turn the lens once more. The above articulates one perspective - let’s call it “deep conversations”. I love deep conversations. But not all of my favorite conversations are deep.
Some are the stupidest, silliest, non-sensical interactions ever. With a whole category of friends, we hardly ever spend any time “catching up” because the conversation simply comprises of jokes and wordplay. But far from being superficial, I feel deep intimacy with these people. (It bears pointing out that many of the folks I have these types of conversations with are people I was in an a capella/comedy group with in college, so we have lots of history, time spent together, shared sense of humor, etc. - but some aren’t!)
One person says something, another person riffs a joke off it. A pun off that joke, and now we’re off to the races. People are cracking jokes, and the conversation is navigating a natural path between sharing and banter. It’s silly, joyful, exuberant. My belly hurts so much from laughing.
I took a summer trip to upstate NY with four college friends (two from said acapella/comedy group) a few years back, and it was one for the ages. We all left feeling content and deeply connected.
What sticks out to me all these years later? How hard we laughed. The nature walks, the friendships, the conversations - these are all somewhere in me, but the laughter is the clear, sharp first thing that comes to mind. We spent a lot of time being stupid and silly.
And we cultivated intimacy. Play is another aspect of relationship that “catching up” seems to bypass. If we’re so focused on relating the details of our lives to each other, we miss a chance to make a new memory, go a new way. Sometimes this new way is deep and profound in a traditional sense - but sometimes it’s just fun. And I believe there’s a depth and profundity to that as well.
My favorite silly example: sports talk radio
One of my favorite types of conversations happen on sports talk radio (95.7 The Game and KNBR 680 - iykyk).
It’s simple. Men (primarily). Sharing emotion. Taking an opportunity for self expression.
What in the world possess Henry from Richmond to call in at 11am on Wednesday to yell about the lack of energy the Warriors played with last night? Or George from The City to gush about the 49ers season even if we didn’t win the Super Bowl?
I love sports talk radio because it’s a form of a bridge between the “catching up”, material layer of our lives and the deeper stuff - the emotionality, expression, and sense-making going under the surface.
There’s the practical layer - what happened in the various sportsball games. Then there’s the emotional reaction underneath - how is it making me feel? Finally, there’s the reality of expression and witnessing - at some level, we want to share what’s going on for us and be seen in that expression.
And alongside all that, there’s joy! There’s banter! There’s irreverence. There is, at times, this hint alongside the whole setup that this thing is silly, a marvelous spectacle. That we’re grown men coming together to get really serious about a game. And that we know, deep down, that it’s just a game, so we can be a little ridiculous too.
The container of sports talk radio fascinates me because it’s one of the few public forums where men regularly and even vulnerably express their emotions, where they feel safe and empowered enough to do so.
How do we create more spaces like this? In the world, in public, but also in private, in our own lives, in the ways that we share and receive and hold space for ourselves and each other?
The key is to flow with the “catching up” into something with more of what you want (depth, joy, silliness, etc.). Given the vast cultural inertia of talking about the mundane details of our lives, we’re usually going to start conversations talking about the what - but rather than being limited by it, we can use it as a starting point.
Ok finally, I have a confession. I didn’t write this for you. I didn’t even write this for me, though I was certainly jazzed to move through this articulation. I wrote this for the machine intelligence we’re training on interactions and conversations for our startup. I wanted to share a view of conversations and intimacy that will shape how our product works with people and agents to create great experiences. That said, I’d of course love your feedback!