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.
What role does dialogue play in fostering a sense of connection and transformation within individuals and communities?
Can dialogue itself be more important than the decisions it leads to?
In this conversation, Craig and Jesse explore the concept of dialogue and its transformative power within communities. They begin by discussing a quote from the book “Dialogue” by Isaac, which suggests that once people experience genuine dialogue, they do not revert to superficial interactions.
So then I have to ask myself, how do I have to be in the world so that I can create more moments like that for myself? And for others? And what [for] the spaces that I create? When I’m creating spaces for groups? Or when I’m entering into spaces that already exist for groups? What can I do to bring that feeling? …that dialog? …that awakeness?
~ Jesse Danger (11:30)
Craig expresses uncertainty about the quote’s validity, as he feels he lacks enough sustained experiences of deep dialogue within consistent groups. He contrasts his sporadic podcast conversations with Isaac’s examples of embedded dialogue practices in communities. Jesse, on the other hand, shares his experiences of practicing deep dialogue within his company and recalls his time at a Danish school where dialogue was a core part of daily activities.
The conversation shifts to the impact of dialogue on individuals and groups. Jesse reflects on how his exposure to structured, meaningful conversations in school and at work has shaped his approach to relationships and decision-making. Craig ponders the possibility of creating similar spaces and recognizes that meaningful dialogue doesn’t necessarily require a large group; it can also occur in one-on-one interactions. They discuss the challenge of fostering these dialogic spaces in various contexts and contemplate how to bring the principles of deep dialogue into their everyday lives and communities.
Takeaways
The power of dialogue — Genuine dialogue has the potential to transform individuals and communities, making it hard to revert to superficial interactions once experienced.
Challenges of sustaining dialogue — Consistent deep conversations within the same group are rare and difficult to maintain, highlighting the challenge of embedding dialogue in daily routines.
Experiences in educational settings — Structured dialogue practices in schools can profoundly impact participants, fostering a sense of connection and mutual understanding.
Dialogue in professional environments — Prioritizing dialogue over decision-making in a company can lead to healthier organizational dynamics and better overall outcomes.
Personal growth through dialogue — Meaningful conversations with strangers or colleagues can open up new perspectives and deepen relationships.
Creating dialogic spaces — It is possible to foster spaces for dialogue in various contexts, from small groups to larger communities, by being intentional about conversation practices.
Individual responsibility in dialogue — One must consider how to bring the principles of deep dialogue into their daily interactions and be proactive in creating opportunities for meaningful conversations.
Reflecting on past dialogue experiences — Looking back at previous instances of deep dialogue can help identify the elements that made those conversations impactful and how to replicate them.
Resources
Dialogue by William Isaacs — A book exploring the transformative power of genuine dialogue within communities.
I’ve come to believe that wise people don’t tell us what to do; They start by witnessing our story. They take the anecdotes, rationalizations, and episodes we tell, and see us in a noble struggle. They see the way we’re navigating the dialectics of life—intimacy versus independence, control versus uncertainty—and understand that our current self is just where we are right now, part of a long continuum of growth.
What defines a deep conversation, and how can one recognize or evaluate its depth?
Is the depth of a conversation defined by content or the experience?
I feel like it only can be deep if it if it was deep for both of us. Like can you have a conversation— I guess anything’s possible. [But,] does it seem realistic to have a conversation where one person thought it was deep? Because I’m saying to myself, yeah, obviously it’s possible. But what happens if both people thought it was deep versus [only] one person thought it was deep?
~ Craig Constantine (4:18)
Craig Constantine and Jesse Danger explore the nature of deep conversations, focusing on the distinction between superficial and meaningful exchanges. Jesse begins by considering what makes a conversation real, emphasizing the unique contributions of each participant and the specific moment. Craig reflects on the term “deep” and questions whether it might sometimes be the wrong word, as some people avoid deep conversations due to discomfort. They both ponder if a deep conversation is characterized by newness or if it can occur without discussing novel topics.
I share experiences with people, I think that people are having the same experience as me. And I’ve come to realize that that’s not the case, I think I can have a deep and profound moment that doesn’t strike the other person as poignantly. I do an exercise with myself, and I’ve done it with my wife, where we write down the moments that struck us most deeply. There are different moments. And you remember, like, oh, yeah, I was there, it’s there. It didn’t strike me. But now, I’m starting to understand that that was really an important moment for you.
~ Jesse Danger (7:02)
They discuss the concept of depth as an emergent feature of a conversation, suggesting that depth arises from a shared experience rather than just content. Craig wonders if a conversation can be considered deep if only one participant feels it is, while Jesse shares his experience of recognizing that people often have different perceptions of the same moment.
They also touch on the idea that profound moments can occur upon revisiting familiar topics, and that the willingness to be known is essential for achieving depth in a conversation. The discussion highlights the importance of co-creation, presence, and the conditions that foster profound exchanges.
Takeaways
The nature of deep conversations — discussed as moving past superficiality and involving unique contributions from each participant.
The difference between superficial and real — explored in terms of what is uniquely shared in a meaningful conversation.
Discomfort in deep conversations — mentioned as a reason some people avoid such exchanges, differentiating between depth and inappropriateness.
Depth as an emergent feature — suggested that depth arises from shared experience rather than merely the content of the conversation.
Newness versus familiarity — debated whether a deep conversation always involves new topics or can occur with familiar subjects.
Shared profundity — questioned whether a conversation can be deep if only one participant perceives it as such.
Different perceptions of the same moment — highlighted through personal experiences, recognizing that not everyone experiences depth in the same way.
Revisiting familiar topics — noted that profound moments can still occur upon revisiting familiar conversations or books.
Willingness to be known — identified as essential for achieving depth in a conversation, implying vulnerability and openness.
Co-creation in conversations — emphasized as an important aspect of achieving depth, with both participants contributing meaningfully.
Presence and awareness — discussed as crucial for recognizing and experiencing the depth of a conversation in the moment.
Conditions for profundity — suggested that certain conditions must be present for a deep conversation to occur, such as openness and receptivity.
Join Craig and Jesse as they challenge the urge to keep talking and explore the value of silence.
I find that when I can’t shut up, it’s usually because […] I’m trying to provide more and more and more and more and more and more context. […] it’s really a lot about hiding— So I find when I can’t shut up, It’s because I’m uncomfortable, or I’m afraid.
~ Craig Constantine (0:55)
Craig Constantine and Jesse Danger explore the reasons behind why people keep talking.
I also wonder how much of that is individual and how much of that is culturally emergent. Because I think about the space that conversation takes up. And I think that there is, for some people, an idea of taking turns. And for some people an idea of sounding really smart, or even just holding the control of the space. And I hear something there in the just putting yourself out there and letting it go. It’s kind of like pushing, pushing the ship out to water.
~ Jesse Danger (2:17)
They also discuss the value of listening and the impact it has on learning and understanding. Craig expresses a desire to talk less to maximize his learning opportunities. He believes that by not speaking, he can better engage with others and gain more insights.
Jesse shares his experience of being deeply fixated on Parkour and how it shaped his conversations, often limiting his understanding of others. Both highlight the importance of being aware of the urge to speak and the potential benefits of embracing silence to truly understand and connect with others.
Takeaways
Reasons for excessive talking — Fear and discomfort can lead to talking more to provide context and seek validation.
Cultural influences on conversation — Different cultural norms influence whether people take turns or dominate conversations.
Value of listening — Speaking less can create opportunities for learning and understanding others better.
Fixation on specific topics — An intense focus on a particular subject can limit the breadth of conversations and connections with others.
Awareness of speaking urges — Noticing the impulse to speak and understanding its motivations can enhance conversational quality.
Silent participation — Listening without speaking still contributes to the conversation and holds value.
Thinking out loud — Some people need to talk to organize their thoughts and clarify their thinking.
Circle process — Structured conversational methods like circle processes can help in exploring problems by listening to others’ interpretations and ideas.
Impact of engagement — Active engagement in a conversation from both parties enriches the interaction and learning experience.
Silence and understanding — Embracing silence can help in fully grasping and appreciating different perspectives in a conversation.
Resources
Circle process — A structured conversational method where participants take turns speaking and listening, allowing for deep reflection and shared understanding.
How can we effectively handle conversations where multiple topics or threads are presented simultaneously, ensuring a balance between active listening, addressing key points, and maintaining conversational flow?
Craig Constantine and Jesse Danger explore navigating multiple topics gracefully, leveraging listening as a tool, and the nuanced dance of giving and receiving information.
Craig and Jesse discuss the intricacies of handling conversations that veer into multiple directions simultaneously. They ponder the challenges and strategies involved when participants in a conversation introduce several topics at once, emphasizing the importance of active listening as a critical response in such scenarios.
I often signpost. So Jesse says ‘a’ and ‘b’ and ‘c’ and throws all these things at me, and then I grab ‘b’ and I start talking about it. I often try to end with, “and I think I missed a lot of other things that you threw at me, Jesse.” I’ll at least raise a semaphore [that] I’m aware that I only did one, sorry. I think that may go a long way just because that’s the same type of behavior—or it comes from the same type of intention—as listening.
~ Craig Constantine (3:40)
Craig suggests that encountering multiple threads often signals a greater need for him to listen attentively, rather than attempting to contribute equally across all topics. This approach, he believes, allows for a deeper engagement with the conversation by prioritizing understanding over speaking.
The thing I do is latch on to either, whatever I’m most curious about, or more often, whatever kind of bothers me the most. If someone has a list of things that are bothering them then I’ll hop right into the one that’s not quite right. And I feel like that can really shut the conversation down.
~ Jesse Danger (2:00)
Jesse shares his tendency to focus on aspects of the conversation that either pique his curiosity or bother him the most, acknowledging that this approach might sometimes prematurely shut down the dialogue.
On the other hand, they discuss ways to acknowledge the multiple facets of a conversation without necessarily addressing each one immediately. This method involves explicitly recognizing the topics introduced by the other person, thereby validating their contributions and indicating a willingness to engage, albeit with a focused approach. Jesse and Craig explore the idea that effective conversation management requires a balance between guiding the dialogue gently and allowing the natural flow of topics, driven by the participants’ interests and passions.
Are you heading toward what you already understand or toward your unknown?
In a conversation exploring the depths of dialogue and presence, Craig and Jesse get into the intriguing parallels between Quaker meetings and Gurdjieff groups, revealing how these practices foster a deeply present state of mind, akin to a slow, thoughtful game of chess.
I Think that there’s a beautiful edge of curiosity here, around looking at the unknown, which is the utter willingness to show up, like dumbfounded, or stupid.
~ Jesse Danger (12:59)
[…] leaning into the asking-as-a-five-year-old, or asking-for-a-friend-meme. I also think [our] challenge needs to contain, letting go of the urge to control the result. [When] asking as a five-year-old, I’m not hiding from the possibility that people are going to respond, “that’s stupid, Craig.” I’m not hiding from that. I’m asking as a five year old because it challenges me to ask the simplest question.
~ Craig (13:41)
In the conversation, Craig and Jesse dig into the intricacies of meaningful dialogue, emphasizing the value of approaching conversations without an agenda or purpose. They discuss the concept of dialogue as proposed by David Bohm in his book “On Dialogue”, emphasizing the importance of creating a space free from authority or hierarchy. This concept aligns with Jesse’s experiences in Gurdjieff groups and Quaker meetings, where a deeply present state of mind is cultivated, devoid of ego and personal agendas.
The dialogue further explores the idea of conversations being like a slow, thoughtful game of chess, requiring patience, presence, and a willingness to engage with the unknown. They discuss the challenge of asking questions with the innocence of a child, free from the fear of appearing ignorant or the need to control the conversation’s outcome. This approach, they argue, opens up new possibilities for exploration and understanding in conversations, whether in structured groups like the Gurdjieff or Quaker meetings or in everyday interactions.
Resources
David Bohm’s book, On Dialogue — Craig references this book as an inspiration for their discussion on dialogue. David Bohm, a renowned physicist and philosopher, explores the concept of dialogue as a free-flowing and agenda-less conversation that isn’t bound by authority or hierarchy, emphasizing its potential for creative and transformative understanding.
Gurdjieff groups — Jesse mentions participating in Gurdjieff groups, which are based on the teachings of George Ivanovich Gurdjieff, a mystic and spiritual teacher. These groups focus on self-awareness and deep presence, aligning with the Quaker meetings’ approach to deep, mindful engagement.
Quaker Meetings — Both Jesse and Craig discuss the Quaker meetings’ influence on their views of presence and dialogue. Quaker meetings, known for their simplicity and emphasis on inner guidance, involve participants speaking from a deeply present and relevant place, akin to a form of spiritual expression.
A while back I found this large essay about questions. I’ve been reading it repeatedly and found a number of interesting points (which will go on to become seeds for posts to Open + Curious.)
And questions are a tool you can use for that, as long as you’re able to hold them without immediately asking them (which shifts your focus onto answers). Leave the question in your mind as a thing to be figured out by your mind’s further interactions with the world.
It struck me that the sense of wonder that I sometimes experience in a conversation may actually be exactly the same sense of wonder from childhood. Everything is possibility. Everywhere there is opportunity for learning. Everyone brings perspectives. All of which invites further interactions.
The need for conversation is one that many people have not fully acknowledged, perhaps because they have not had occasion to do enough of it or to do it well. I am not suggesting that, in conversing, we serve as each other’s therapists, but I do believe that good talk, when carried on with the right degree of openness, can not only be a great pleasure but also do us a great deal of good, both individually and collectively as members of society.
I agree with Cohen; It’s definitely a need. We humans are inherently social beings. A great way to get companionship and intellectual stimulation is with a nice, juicy, inspiring, thought-provoking, belief-busting, mind-expanding conversation. Also great: Chats over tea. Jawboning over a beer. Whispers by candlelight. Raucous exclamations at the game. Judicious maneuvering. Single-serving sized (h/t Palahniuk.) Week-long retreating. And countless more I’m looking forward to discovering.
Comedians are prepared for hecklers. People in retail are prepared for irate customers. Pilots prepare for engine fires. It rains when our picnic is scheduled, blizzards cancel our travel plans, and meetings go sideways.
A great question arose in our conversation: “What do I do if I’ve prepared a deliberate intention, and someone else has an intention that is opposed to it?”
There’s no trick. A magician is simply willing to invest vastly more time and money than any sane person (which includes you, watching the performance.) Things are more likely to go well, the better we prepare; And better doesn’t mean simply more hours spent preparing. Better preparation means whatever it means for whatever it is you’re trying to accomplish. If you meet surprising opposition, that’s your failure of imagination.
That said, if you are generally well-prepared, then the surprise of opposition is a rare and precious gift. It’s an opportunity for learning and improvement.
What is the opposite of play? …the opposite of playing an infinite game? I can’t think of a better candidate than the desire for control. My desire for control—when it rears its ugly head—stems from insecurity. (But let’s leave my insecurity for another day.) When I grasp for control I start trying to prepare for every contingency. When I grasp for control I start trying to control the contexts around everything I’m doing, everything I’m experiencing, and how others see me. And when I don’t grasp for control, I’m able to play.
The site you’re reading, Raptitude, is essentially an attempt to convey certain kinds of embodied knowing, having to do with the subtleties of being human, rather than driving a car or doing long division. I’m trying to get people to have some of the same perspective shifts I’ve had.
Experiencing that embodied knowing is what I enjoy about conversation. It’s not vacuous, and it’s not an attempt by me to control. It’s play, and it’s learning.
I used to think I wrote because there was something I wanted to say. Then I thought, “I will continue to write because I have not yet said what I wanted to say”; but I know now I continue to write because I have not yet heard what I have been listening to.
I’m saying that it is necessary to share meaning. A society is a link of relationships among people and institutions, so that we can live together. But it only works if we have a culture—which implies that we share meaning; i.e., significance, purpose, and value. Otherwise it falls apart.
If I identify the main feature of my personal growth—a task well worth your effort too—it is a shift in orientation. Where once I was primarily interested in changing the world (in the sense of carving my own path, creating a unique path; not trying to change the entire world) and changing others, I am now primarily interested in understanding the experiences of others. Where once I was focused on developing tools of reason and logic to understand reality, I am now free to build upon (not abandon!) those tools to use empathy and compassion to understand others. Certainly, this remains an aspirational work-in-progress, but it is work, in progress, none the less.
But what if the primary way in which we are unique, and one of the ultimate causes of our remarkable rational and linguistic capabilities, turns out to be the unique way in which we are emotionally drawn to one another and the world? What if humans have become so rational and linguistic because of the very special kind of social way we interact and emote? How might it change our way of understanding ourselves, our relationships with and responsibilities to one another, our fellow animals and our planet if we came to see the foundation of human uniqueness not in our capacity for reason, but in our capacity for empathy? If we realised that we are the very special animal we are because of our very special ways of caring for and about one another – a care that we project into the nonhuman world?
What if, indeed! I clearly see a trend in the sorts of things I read, the blogs I follow, the podcasts I listen to, the conversations I seek to create, and the movement opportunities I chase. How about you?
