Great Conversations

Throughout my final couple of weeks living in San Francisco, I've found myself in a naturally reflective period. During big transitions, I find that I have 3 top priorities:

1) connecting the new stories of my life that have appeared in the past season

2) preparing and planning for the next phase

2) watering my relationships with the hopes that they’ll hold up until I can tend to them again

This time around, the watering process took the shape of 1:1 walks with my friends, team, and mentors, resulting in a 6x week-over-week increase in step count.

During, between, and probably because of these walks, I've been paying extra close attention to how different types of conversations feel, from the small talks and the catch-ups, to the professionals 1:1s and the daily standups.

In the process, I’ve identified a genre of interaction that I’m going to call Great Conversations. Great Conversations take us to a specific “mind space” that I can only really describe as flow state; it’s a state of consciousness characterized by complete immersion, a warped sense of time, and a smaller sense of self. These conversations often consist of trading ideas, building abstractions, speaking in metaphors, and exchanging stories.

I’m not only convinced that Great Conversations are key to developing real and deep connections, but I'm almost convinced that they might even be what we refer to as a ~real and deep connection~ in the first place.

But if Great Conversations feel so good, why don’t we have them more? Or just have them with everyone all the time, for that matter? In this post, I'll explore some observations I've made about the nature of Great Conversations, why they’re so rare, and what work we can do on ourselves in order to foster more of them in our lives.

The truth is conversational flow state can be difficult to find, achieve, and cultivate. It requires a delicate balancing act of the participants’ worldviews as well as their desire to share them in the first place. In order to better understand what it takes to foster Great Conversations in my own life, I decided to lean on related ideas I've come across for cultivating this presence for activities in other domains.

Although I could use Mihaly Czikzentmihalyi’s classic definition of the “flow state” as a starting point, I instead kept coming back to an older idea that I came across in high school: Malcolm Gladwell’s definition of “meaningful work” from his book Outliers.

Gladwell describes 3 key criteria for identifying Meaningful Work which I've (anecdotally) found to be closely aligned with if not identical to the criteria it takes to achieve flow state across most domains. Gladwell hypothesizes that Meaningful Work consists of the following criteria:

1) Complexity

2) Autonomy

3) A clear relationship between inputs and outputs

The work that fulfills us, the work that connects us to ourselves and to source, must be work that takes us to the edge of our abilities (complexity), gives us the freedom to explore our intuitions, curiosities, and limits (autonomy), and gives us a sense of forward progress through tight, iterative feedback loops (input <-> output relationship). Activities with these characteristics enable us to explore and transform ourselves through rich, dynamic interaction with our environments.

Engaging in activities and conversations that take us to the edge of our abilities demands us to silence much of the discursive thought to which we are accustomed (and even addicted) and instead listen intently to visceral signals in ourselves and in our environments for clues about the next best step to take. When we're in just the right work environments or tackling just the right challenges, we can quietly tune into these signals and instead operate on intuition and internal feelings, bringing us deeply into the present moment.

While finding flow state through single-player games like programming, painting, or running can provide a rich experience in and of itself, few activities provide more fulfillment than co-creating flow state with others. So, reflecting on both the rarity and preciousness of these interactions in my own life, I've noticed that reaching this state through multi-player conversation requires basically the same conditions as achieving this state alone: complexity, autonomy, and immediate feedback. The person or people on the other side of the exchange must be able to understand, challenge, and stretch your worldview in order to stimulate self-exploration. You should feel your worldview unraveling all by itself, effortlessly and iteratively throughout the engagement.

Bad conversations, just like good ones, might attempt to start at places of shared understanding but never really “hit” any particularly engaging or challenging topics. Uninspiring conversations like this will often float aimlessly in circles around trivial topics that remain safely in your shared understanding of the world (or else fail to ever find common ground in the first place).

Stimulating conversations with “mentors” (and I use that term loosely) also rely on starting with shared ground, but have the primary objective of stretching only the mentee’s understanding of the world. These conversations usually begin with a short calibration process while the mentor identifies the gaps in his students’ knowledge and uses both his worldview and the student’s existing knowledge as anchor points in the conversation.

While my mentors and teachers are usually more than capable of pushing me to my edge, I've noticed that the stimulation needs to be bidirectional in order to be sustainable. Both parties need to feel challenged in order to remain engaged and uninhibited by discursive thoughts, or else risk dancing on the edge of only the students’ worldviews, causing the growth and resonance to move unilaterally.

The best conversations instead oscillate back and forth between both party’s unique knowledge and experience to expand both people’s personal and shared understanding of themselves and of the world. This momentum and back and forth is what I picture when people say that something “resonated” with them; the ideas being discussed echo against the edge of their worldview and stretch it wider, little by little.

For this reason, I've found that Great Conversations are easiest to sustain with friends and peers with whom it's easiest to have symbiotic growth through conversation– sparring partners who feel just as free, challenged, and transformed by your worldviews as you are by theirs.

With these frameworks in mind, we can revisit our main question: why aren’t Great Conversations as common as we might hope? The key, I believe, lies in the delicate conditions that it takes to foster them. In contrast with single-player games, co-creating conversational flow states (anecdotally) requires both parties to display confidence and vulnerability and to have intersecting but unequal knowledge about the subject at hand, as well as mutual trust. These ingredients endow us with both the competence and mutual incentive we need in order to push each other’s worldviews and guide each other into flow, thus deepening our connection to each other.

Reflecting now on my farewell walks through Golden Gate Park, I recognize that Great Conversations have been the cornerstone of my experience in this city. As I transition into my next adventure, I carry with me the wisdom that the quality of our experience depends on the depth of our curiosity, vulnerability, and conversations.