Writing out a list of topics and connections is good but it’s only one part of a conversation. You should also consider various reasons for having a conversation. For instance: passing the time, relieving anxiety, developing a relationship, maintaining a relationship, exchanging information, keeping updated on important information, debating a substantive point, getting someone to relax before asking them for something, being polite, making someone feel welcome, resolving a conflict. And when people have different goals for a conversation, it can be uncomfortable. If someone starts talking when they are nervous and you want to discuss the finer points of evolution, both people will get annoyed. When you are nervous, you want to talk about inane things because they are simple and an easy distraction; talking about science might be too complicated and compound your anxiety. Similarly, if you are really in the mood to talk complex subjects, you don’t want to talk about irrelevant, silly things and can get annoyed because the other person has nothing to offer. (Of course, some people might find talking about science comforting, even if you find it boring. There is no fixed relationship between the inane/serious topic scale and the frivolous/deep conversation scale.)
So, you should develop your ability to know why you and the other person each want to have a conversation. Moreover, you should improve your ability to engage in various types of conversation. Often times, if you start a conversation on their terms, they will get comfortable with you and later on have the conversation you want.
You also have to think of conversation as a bargain between two people. You have a set of topics and conversation types you like/are strong at/want to do and the other person has hers. As with any negotiation, you have to work towards a mutually acceptable compromise. Of course, expanding your list of topics is helpful, because it increases the odds you will find common ground for someone, but your concept map does not necessarily help you quickly find something in common to talk about with another person.
I have an idea that I would like to float. It’s a rough metaphor that I’m applying from my mathematical background.
Map and Territory is a good way to describe the difference between beliefs and truth. But I wonder if we are too concerned with the One True Map as opposed to an atlas of pretty good maps. You might think that there is a silly distinction, but there are a few reason why it may not be.
First, different maps in the atlas may disagree with one another. For instance, we might have a series of maps that each very accurately describe a small area but become more and more distorted the farther we go out. Each ancient city state might have accurate maps of the surrounding farms for tax purposes but wildly guess what lies beyond a mountain range or desert. A map might also accurately describe the territory at one level of distance but simplify much smaller scales. The yellow pixel in a map of the US is actually an entire town, with roads and buildings and rivers and topography, not perfectly flat fertile farmland.
Or take another example. Suppose you have a virtual reality machine, one with a portable helmet with a screen and speakers, in a large warehouse, so that you can walk around this giant floor as if you were walking around this virtual world. Now, suppose two people are inserted into this virtual world, but at different places, so that when they meet in the virtual world, their bodies are actually a hundred yards apart in the warehouse, and if their bodies bump into each other in the warehouse, they think they are a hundred yards apart in the virtual world.
Thus, when we as rationalists are evaluating our maps and those of others, an argument by contradiction does not always work. That two maps disagree does not invalidate the maps. Instead, it should cause us to see where our maps are reliable and where they are not, where they overlap with each other or agree and are interchangeable and where only 1 will do. Even more controversially, we should examine maps that are demonstrably wrong in some places to see whether and where they are good maps. Moreover, it might be more useful to add an entirely new map to our atlas instead of trying to improve the resolution on one we already have or moving around the lines every so slightly as we bring it asymptotically closer to truth.
My lesson for the rationality dojo would thus be: -Be comfortable that your atlas is not consistent. Learn how to use each map well and how they fit together. Recognize when others have good maps and figure out how to incorporate those maps into your atlas, even if they might seem inconsistent with what you already have.
If you noticed, this idea comes from Differential Geometry, where you use a collection (“atlas”) of overlapping charts/local homeomorphisms to R^n (“maps”) as a suitable structure for discussing manifolds.