A week ago, I had an amazing conversation with Brennan and a few others at Edyfi. You know the type: it went on for hours, flowing powerfully from Taleb’s essays about black swans, to startup and literary pursuits, to powerful revelations on culture and motivation. It could have gone on for hours more if not cut off by the late hour.
It was only the third day we were at the house. As the conversation closed, we expressed our excitement for many more revelatory conversations like it. But, as someone who has had similar conversations and been in similar situations before, I had the sense that another one was not to come for a while, at least of the same duration and intensity.
Good conversations are amazing. They’re where the most interesting intellectual connections and relationships are forged, insights and ideas that revolutionize industries or fields of study.
In the week since that conversation, I’ve written multiple blog posts and mentored dozens of students as they submitted applications for and are preparing to give talks at an event next week. I had a conversation with a friend about how to self-reflect, learn about yourself and the world from your experiences, and turn it into writing like I do on my blog, and another about the very act of learning and innovation.
What I’ve come to realize is that the same principles govern not just what makes good person-to-person conversations, but all manner and scale of internal and external dialogues. In this blog post, I’ll share a few conditions I’ve identified that facilitate all internal and external learning, innovation, and creativity.
The day after our initial conversation, Brennan asked me to share my knowledge about Existentialist philosophy with him. I replied that my knowledge is pretty limited, but I could share my understanding of the small amount I had read.
“Whatever you know, I just want to absorb as well,” Brennan replied. “My unfamiliar-mental-model detector keeps going off around you.”
This triggered the first insight: good dialogues occur when there is a gap in knowledge or thinking to be crossed.
This is an intuitive idea to grasp. A conversation in which you are entirely in sync with other participants – same beliefs, perspectives, source readings – isn’t likely to be very interesting. Similarly, reading a book conveying familiar knowledge with familiar framing isn’t likely to be valuable. Human curiosity drives us to seek out the new and surprising; only when your conversation partners, be they friends or authors, present you with ideas and experiences differing from your own do you experience the thrill of good conversation and the synthesis of new thoughts.
This straightforward idea of interesting dialogues arising from a sync gap has non-trivial implications, however.
For one, this sync gap being the root of good conversations is the pattern I recognized when I felt that another good conversation with Brennan and others was unlikely to happen for some time after the initial one. We entered the conversation more or less as strangers, with significant sync gaps, each bringing our own experiences and philosophies. Recognizing and building bridges over these sync gaps were what drove our conversation into the night.
The byproduct of this, though, is that the amount of available gaps to surface up in conversation has decreased significantly. We’ll have to work harder, or encounter deeper and broader catalysts, to recreate the same abundance of mental chasms to cross. In fact, counterintuitively: the better the initial conversation, the more chasms are bridged over, and the harder it is to find new chasms for good later conversations.
The idea of new thoughts stemming from sync gaps also speaks to a deeper truth about creativity and thought synthesis. New thoughts do not come out of nowhere, nor do they emerge as a linear progression of accumulated experiences and knowledge. Rather, discovery and innovation is found only in the gap between conflicting ideas or experiences. Fundamentally, creativity is a process of building connections between existing ideas, not synthesizing completely new ones.
This truth asserts not only the value, but the necessity of intersectional pursuits for learning and changemaking. Whether across disciplines of knowledge or across conflicting directions in the same field, differing perspectives and opinions are the source of intellectual progress.
This is not nearly a call to devalue your current beliefs and seek out diametrically opposing ones, however.
The second condition for good dialogues is a subcondition of the first: the size of the sync gap matters. If the gap is too big, it will be too difficult to bridge over with momentum. If the gap is too small, it will be too insignificant for a bridge over it to create momentum.
This principle should also seem intuitive. Though a 40 year old most likely has a much richer collection of experiences and many more sync gaps with me than a 20 year old, I’m more likely to sustain a stimulating conversation with the 20 year old who has experiences much more similar to mine, but just different enough to create a flowing back-and-forth dialogue. Conversely, the fact that I learned calculus at a different school than my friend is most likely not interesting.
Once again, though, this principle has non-trivial implications.
Last night, I was talking to Mukundh Murthy, a friend working to tackle antimicrobial resistance (i.e. superbugs that rapidly evolve resistance to all antibiotic treatments). “It’s one of the most complicated problems I’ve come across,” he tells me, conflicted over whether to pursue a solution as the leader of his own team or a member of a more qualified one.
Mukundh brings up the idea of flow state, a state of mind in which one accumulates knowledge and builds innovative solutions seemingly effortlessly (“also known colloquially as being in the zone,” Wikipedia humorously informs us).
The achievement of flow state is a function of your existing skill in and novel challenge provided by the task at hand. If you’re good at doing something and there’s nothing new to learn, you’ll get bored of doing it. If you’re bad at doing something and it’s very difficult to grasp, you’ll get anxious or frustrated and give up. With the appropriate balance of existing skill and novel challenge, though, one can enter a flow state, in which there is a continuous feedback cycle of curiosity and confidence that drives one forwards.
The goldilocks ratio of challenge to skill is 104%, Mukundh tells me.[^104perc] That is, you’ll be at your most energized and productive doing something 4% harder than what you’ve done before.
Meaningful problems – say, growing your first startup, or doing high-impact biotech research – are usually far more than 4% harder than what you’ve done before. Ambitious people and initiatives regularly strive to “10x” themselves or their industries, after all.
But that 10x-ing cannot happen in one step, it can only happen in compounded smaller steps. These steps may be more than 4% steps; you might take 6% or 8% steps, pushing yourself beyond the boudns of naturally occurring progress. By doing so, though, you miss the momentum that 4% steps can create. Perhaps 4% actually is a hard lock on what our brains are able to absorb in a single step, and your perceived 6% or 8% steps are just multiple 4% steps crammed together.
When used properly, though, these small 4% flow-state steps can be immensely powerful. I’ll point to my own experiences with web dev/software engineering as an example. My journey didn’t start with the goal of becoming a web developer. Rather, I just wanted to tweak around a template a friend had coded for me, learning bits and pieces of CSS as I did so. Eventually, I switched to another platform and played around with templates there, getting a sense of templating languages. With each iteration I learned a few new things and polished a few old skills: adding an image slider with JQuery. Using CSS pseudo-classes. Generating my site and hosting it on Netlify with Jekyll. Compounded over five years, these 4% steps got me to the point of being as competent of an engineer as most new CS grads.
Similarly, any large idea or project needs to be broken down into smaller 4% pieces to be understood and executed.
Learning is effectively a dialogue between yourself and your learning materials, while solving a problem is a dialogue between yourself and the problem at hand. Working backwards, the 4% principle applies quite well to literal conversations. The best conversations introduce new connections in iterative ways, not completely new ones.
After reading some of my blog posts, an old friend messaged me asking how I come up with so many reflections and insights about my life experiences. “It’s so hard for me to find meaning about things from myself,” she says. “I need people to have opinions first before I can build up my own.”
To me, that last point is not a shortcoming, but a truth about the process of thought synthesis. As I’ve written above, thoughts are not created out of nothing, but created out of connections between existing ideas. Self-reflection and writing is not an exception to this rule, but rather a nuanced example of it.
I’ve long compared journaling to having a conversation with myself. I journal to unpack the sources of stress and unhappiness in my life, as well as things I’m grateful for, and lay out steps to move forwards or larger ideas that emerge.
At first glance, there doesn’t seem to be more than one participant in this conversation; but I would argue that there is.
The self that you constantly experience is fundamentally transient: it only exists in the current moment. As soon as the moment passes by, that self is gone, replaced by a self with infinitesimally updated experiences and thoughts.
This transient nature is why it’s hard to sustain meaningful dialogues with yourself through thought alone. Ideas may persist or fade away at a moment’s notice, and there is no source of externality or feedback other than your own momentary thoughts.
When you write down thoughts on a page or document, on the other hand, you’re creating a version of you that persists through time, one that is no longer confined to the moment. Now, from the momentary solidarity of your mind, you’ve created an externality that you can interact and converse with.
This externality is what makes journaling and writing so powerful, so much more so than simply thinking to yourself.
When I examine the mechanism behind my relatively prolific blogging over the past few weeks, the best understanding I’ve come up with is that I’ve developed a conversational rapport with myself, or the persistent projection of myself found in the words I write. It’s like having a friend I enjoy talking to: when I have an interesting experience or idea, I automatically turn to the best conversation buddy available to share it, which a few times a week may be myself, resulting in a piece of writing.
On Monday night, applications for the second round of TKS Community Talks closed with 31 submissions. Out of these submissions, a team of three other TKS students and I selected eight talks ot be prepared over the next two weeks and presented to the community.
In the course of this selection, and providing mentorship to speakers before and after they submitted their applications, I developed a basic framework for what makes a great talk. There are two ingredients, I proposed, unique insight and personal connection. A unique insight is the core message of the talk, one that will stay in audience members’ minds and expand their worldviews. A personal connection is a method of delivering that core message in a compelling way, i.e. by tying an abstract mental model to one’s personal journey, or developments in a field to research to a researcher or research group’s progress.
Upon further examination, these two ingredients match up exactly with the two principles for good dialogues laid out in this blog post. A unique insight represents a sync gap between the speaker and the audience. The idea that the insight changes the audience member’s worldview makes this clear: a compelling message necessarily crosses a gap in knowledge. But, in accordance with the second principle of good dialogues, the existence of the gap itself is not enough: it must also be crossed effectively. This is the purpose of bringing in a personal connection or story of some sort: only once listeners latch in and make available their side of the chasm can a bridge be built between the speaker’s idea and the listener’s mind.
This blog post is the latest in my continuous meta-reflections about learning and building.
“How do we think for ourselves?” I asked myself before, in response to realizing just how much of what we think and claim is simply a regurgitation of ideas that have come up before. Asking “bad” questions and appealing to innate human curiosity is the answer I eventually came up with.
This framework of new thoughts arising from connections takes a different direction, attempting to break down the mechanisms by which ideas seem to be regurgitated in the first place.
Frameworks are inherently reduced, fluid representations of the underlying wisdom. This framework captures only one dimension of the operations of thought synthesis and exchange, and in meta-application speaks to its own limitations and fluidity. Yet, it’s a framework that I find immensely useful in application to such things as conversations, writing, public speaking, and learning in general, which are pwoerful mechanisms of self-growth, connection-building, and impact-making