Nothing in the portrait matches exactly what I think of as myself, yet somehow everything about it is exactly right.
Fox, I’m sorry that this took me so long to post!!
Months ago, I was contacted out of the blue by someone who asked to have a recorded conversation for something they called a soul portrait. Being a podcasting nerd, I interpreted their request to be about recording a podcast and I’m always up for a good podcast conversation, particularly when I can be the guest (because then I don’t even have to do any of the hard work.)
We had a fun, single-serving-sized conversation over Zoom where I answered a few questions… and then some time passed before Fox emailed me back.
I’ve looked at that soul portrait countless times, and every time it makes me smile, and brightens my day. My line at the top (“”) is what I wrote to Fox when I saw it. So many details came out subtly right… I didn’t wear glasses as a kid, but I do now; past me seeing future me. Dogs; you had me at “dogs.” Green, the tentacles, that crazy hair… all little details that came out from our conversation.
I’ve recorded a lot of conversations over the past decade — and started my Open + Curious project to explicitly write down what I think I’ve learned. The advice everyone gets about conversation — be warm, follow up, build rapport — doesn’t fully describe what I’ve actually seen happen in the conversations that worked.
This thread is a path through pieces I’ve written and conversations I’ve distilled, sequenced for someone who’s wondering why so many attempts at meaningful conversation fall flat. As usual for my writing, none of them answer the question. Instead, they name some of the gaps between what we usually mean by good conversation and what’s happening when a conversation is actually good.
When it comes, this will be the fourth message received from Alsafi in my lifetime. Few have timed their career so fortuitously. The first came when I was a child. The second came just weeks after I joined the Intercivilizational Observatory’s San Francisco office, and I wormed my way onto the analysis team. The third came the year I met Cassio, and I was doubly lovestruck. Still, I was reading responses to questions another generation had asked. But now, a full 39-year round-trip after I began, I’ll finally get answers to my questions. Ones from my youth, maybe, but they’ll be mine. After all this time, I’ll finally be In Conversation.
This piece of fiction is one of those things I start skimming, thinking “should I mark this for later reading?” and then read it all the way through. So of course I recommend you do too.
I find tremendous value in considered conversation. Usually, a conversation about the weather isn’t such a valuable opportunity. But this conversation about “weather” is really about what are the limits of what can be considered a conversation… is understanding required for it to be a conversation? Or is simply trying to understand, enough?
Introductions are not hard— …we’re just not prepared.
Whenever I’m on a podcast, I dread one inevitable question: “I know who you are, but tell everyone listening who you are!”
This is a moment when I feel painfully insecure, first-day-of-sixth-grade only-kid-with-braces level.
The things I like about myself don’t matter in this scenario; my task is to answer, essentially, “What is interesting, valuable, or remarkable about me to strangers?”
This is doubly related to people around here. Mari goes on to talk about David Nebinski and it’s worth a read.
But also, just yesterday I was in a little session presented by Andrea Wojnicki where she gave (among much more) a tidy little framework for introducing yourself. She pointed out that her framework is a place to begin. Once you get comfy introducing yourself you can expand and modify and do what you like.
So, what’s your current self-introduction?
…then read Andrea’s ideas, and then what’s your new, better self-introduction?
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PS: Technically, it’s triply related since that’s a photo of some of Steve Heatherington‘s alpacas ;)
Conversation is a musical thing, like jazz or birdsong: more ‘call and response’ than question and answer. It enables us to travel great distances, but the joy is in the journey not the destination. We are meant to sing and dance along the way, jamming with others, riffing off them, creating something new right here, right now, in a way that no one can alone.
Be as open as possible to the person in front of you. Listen and observe so closely that you can follow up on a sigh, a shake of the head, a change in tone of voice. Take a chance on reflecting your observations back to them without judgment: “You looked amused just now. What’s that about?” Ask the question about feelings that occurs to you, the one you might normally suppress.
Allow silence.
And see what happens. I think you may be astonished at the result.
Mary Chan is a skilled hostess with a gift for great conversation. Her show is laser-focused on helping other podcasters grow and excel. She recently invited me to join her— …actually, stop reading. Go listen!
Even if we’re lucky enough to “do what we love,” work tends to have tedious aspects we don’t like. Craig Constantine is a passion podcaster who, through the creation of thousands of episodes and rigorous reflection, has built a workflow that simplifies every step of his method, from prep to publication.
Let’s bend relationship advice to apply to podcasting: Feeling stuck in a rut with your podcasting? Go have a conversation with a guest where your entire intention is to be of service to them.
The asymmetry between wanting to know others and being known by them presents an inherent problem, because relationships require reciprocity: If I don’t do the work to know you deeply, a relationship doesn’t form in which you will know me. This vicious cycle—Poe syndrome again—is made much worse when you are lonely to begin with […] In other words, if no one knows you well and you are thus lonely, that may make you more self-focused and less interested in others, making it much less likely for others to want to get to know you well.
Question: What would happen, if your intention with a podcast episode, was to help some else’s well-being— if your intention was only to demonstrate to them that you care? What if you go into it hoping for nothing for yourself?
So not an intention of, “I want to know X, so I’ll ask good questions.”
But rather, “I think they’d enjoy talking about X, so I’ll ask good questions.”
Answer: It’s totally amazing. It alters your own life. You should go do it 500 times.
(Wether or not you turn those conversation into podcasts is irrelevant of course.)
What I’m looking for, in both fiction and documentary, are moments that you weren’t expecting, and which the audience don’t feel prepared for, moments that are candid, like something that just happened in front of the camera, and it’s not going to happen again. Those are the moments you live for as a documentary maker.
I’ve lately been on a bender reading many of these really interesting, really short, interviews with countless people. Most of them don’t particularly interest me. “But wait,” you’re thinking, “those two sentences seem contradictory.” I’m glad you asked about that!
You see, once I know that there’s some large body of work and it’s pretty uniform, then I wonder: Why should I think that the ones I like are the really good ones? Since the work is (pretty) uniform, maybe they’re all really good (or pretty good, at least) and the reason I don’t like most of them… is me. If I sift through the work am I identifying the good ones? …or am I reinforcing, via confirmation bias, my narrow view points? If I wanted to grow—growth often being uncomfortable, especially when it comes to shifting one’s own perspectives—maybe I should intentionally read the ones that I think aren’t that good. Maybe I should be seeking out things which I’m misjudging, and that would by definition be the things I think aren’t that good.
How can you effectively and gracefully end a conversation while maintaining its value and mutual appreciation?
Understand the balance between leaving a conversation fulfilled and seeking more.
Craig and Jesse discuss the complexities of ending conversations, beginning with the idea that most conversations naturally conclude due to external factors like time constraints. Craig notes that in many casual interactions, such as those at events or in public spaces, the end is often dictated by circumstances rather than a conscious decision.
I know I didn’t even try to get everything [from a conversation] because I know I can’t get everything. So it’s somehow finding a balance between: “Okay, my cup is full. I should really move away and just revel in what I have.” Finding a balance between that, and just going to the well until the cup comes up empty. I think that’s probably the compass for how to find a good ending.
~ Craig Constantine (4:25)
They explore the notion that it can be beneficial to end conversations while they are still engaging, rather than waiting until all topics are exhausted. Craig shares his experiences from recording podcasts, where he finds it challenging to end on a high note, emphasizing the importance of planning and strategies for graceful conclusions.
We’re here looking for ways to make conversation more alive […]. I’ve adopted this strategy of, stop eating when I want to eat a little bit more. stop talking when I want to talk a little bit more. Stop training, moving around and exercising when I want to move a little bit more. So that I’m actually left in the wanting of it […]
~ Jesse Danger (5:13)
They also touch on the distinction between enjoyable and uncomfortable conversations. Jesse brings up the idea of stopping activities, such as talking or training, while still wanting more, to maintain a sense of aliveness and enthusiasm. The conversation shifts to practical strategies for ending conversations, including honesty about one’s need to leave and expressing appreciation for the interaction.
Jesse references Peter Block’s concept from the book “Community,” suggesting that when ending a conversation, participants can share what they gained from the interaction, fostering a sense of closure and mutual respect. This approach, they agree, can enhance the quality and impact of the conversation.
Takeaways
Ending conversations naturally — External factors often dictate the conclusion of casual interactions.
Ending on a high note — Beneficial to conclude conversations while they are still engaging.
Challenges in planned endings — Strategies and planning are crucial for graceful podcast conclusions.
Distinction between conversation types — Different approaches are needed for enjoyable and uncomfortable conversations.
Maintaining enthusiasm — Stopping activities while still wanting more helps preserve a sense of aliveness.
Practical strategies — Honesty about the need to leave and expressing appreciation can aid in ending conversations.
Concept of shared appreciation — Participants can share what they gained from the interaction to foster closure.
Spontaneity in conversation exits — Creative and spontaneous actions can make leaving a conversation smoother.
Balancing conversation engagement — Finding a balance between getting enough out of a conversation and not exhausting all topics.
Resources
Community by Peter Block — Discusses the importance of commitment and shared appreciation in group settings.
The concept of “single-serving friends” from the movie Fight Club — Refers to brief, context-specific interactions that end naturally.
