Difficult Conversations 2 [Trenchant Edges]

Welcome back to the Trenchant Edges, where my never beginning battle with Executive dysfunction meets my ambition to create things worth reading.

Too honest? Maybe.

I want to thank you all for bearing with me. This transition has been more complicated than I expected.

A quick update on me: I’m steadily recovering both from reinjuring my back and parting ways with my biggest client, who’s kept my income stable-ish over the last two years.

I’ve effectively taken a lot of September off to rethink what I want to do professionally and how to get there. Not ideal, but it was important.

Do I have clear ideas about where to go next? Not really with anything other than this newsletter.

That kinda sucks, but I’m rolling with it as best I can.

Let’s get back to last week’s topic on difficult conversations.

Bridging Communication Gaps

This post isn’t going to be a list of ways to communicate better or anything like that. I don’t think there are formulaic solutions to problems of human connection.

And even more than problems of reason or evidence, I think connection is the fundamental issue in play.

One of the main uses for beliefs is for social coordination. So we feel like we’re on the same team. This lets us accomplish vastly more than we could as individuals.

Blah blah, specialization is helpful, blah blah.

This is a big reason why feeling alone and disconnected feels so bad. A human alone is a vulnerable human. This also drives our anger and resentment when someone refuses to agree with something that’s obviously true.

It’s important to start with baseline feelings here because one aspect of any discussion will be maintaining awareness of your own internal state. Feelings provide a complex, large pipeline of information about both internal and external states and are a powerful aid in understanding.

So we’ve got one big obvious initial disconnection: When a person is disconnected from their own interior state, they have far greater challenges connecting with other people. Unconsciousness masks where reactions are coming from.

If you’re in an argument with someone and feel bad about it, it’s much easier to blame the other person or misunderstand what they’re saying if you aren’t aware of what their comments are bringing up for you.

But how do you do that?

We’ll be coming around to that question in a bit but let’s suffice it to say that it’s not easy and we all have widely varying moment-to-moment skills with doing so.

Let’s step back and look at the “debate” that got me really interested in this subject: Arguing about religion on GameFAQs circa 2002-2004.

I’ll spare you all my awful teenage atheist phase (Once again, Mom, I’m sorry).

What made me eventually quit those arguments was making friends with the few agnostics on those forums and their arguments that I was being a presumptuous ass who didn’t know what the fuck I was talking about convincing.

They got me reading actual philosophy and theology critically rather than just repeating my biases.

And to this day I have to stop myself from ending arguments with the phrase, “Checkmate, Atheists.”

And Checkmate, Atheists brings us to the point of this digression: Why do people so often act like they’ve made an irrefutable argument worthy of abusing sound recording equipment?

I spent a lot of my 20s thinking about this and observing various arguments where it happened.

And I think it’s the same reason why humans are bad at reading each other’s minds.

It comes down to information asymmetry.

Each of us holds complex networks of ideas in our heads. In a discussion, we build a picture of what the other person’s model is by inference. We use little and big clues to map out a rough estimate of what their mental models are.

Here’s the thing: Because of that approximation, it’s WAY easier to debunk something in your head than it is in someone else’s head.

An example: I’ve seen hundreds of atheists act like the paradox question: “Could God create something so heavy even he could not lift it?” is a real own of theists.

I’ve yet to see it really bother anyone who believed in God. I’m sure it’s convinced someone, but most of the people I see bringing it up were convinced by something else and then went looking for new arguments to support their new position.

There are plenty of comparable examples for proof of god.

In short, it’s easy to oversimplify what a particular belief actually means to people who hold it.

God’s omnipotence doesn't really have much to do with the lived experience of a Christian in a Christian community. It’s more like a node in a vast matrix of senses and smells and there are literally thousands of years of well-tested responses to that kind of logical flaw.

Including the fact that if anything were to have anything resembling omnipotence, it probably wouldn’t be bound by logical sense.

So if you want to understand someone, how do you do that?

Well, if you have two patient people who are reasonably knowledgable in a subject and are willing to spend a lot of time and discuss in good faith, this is pretty doable.

It can be slow and frustrating, but the work is often well worth the effort. I’ve got about 20-30 people I know over the years who I’ve had these conversations with and most of them are people whose friendship I really value.

An example: Back in 2014 or 2015 I got into an argument with an anthropologist about Graham Hancock, who I only really knew from a couple of TED talks where he said some really interesting things about consciousness and censorship.

Well, that was a fucking mistake because the anthropologist in question had been following Hancock’s career for like twenty years and had been debunking him since before he claimed the face on Mars was a sign of an ancient Martian civilization.

Turns out to have been a camera artifact. There is no face on Mars.


So it turns out I was hella wrong to argue with him about Hancock’s sincerity, value, and trustworthiness. The argument lasted like… 3 days. He was right about everything, and I was wrong about everything.

Notice a pattern in these examples?

Admitting you’re wrong is hard, but it’s a bitter pill that usually generates growth.

Alright, I’ve got about 10 minutes before I need to leave and I’m laying down to type.

So it’s time for speed run mode.

Coming Back Around To You

The thing that makes difficult conversations so complicated is there are so many different levels to manage at once and you don’t really control many of them.

From least-you to most-you they are:

  1. Context

  2. Place

  3. The Other Person

  4. What they Say

  5. What you Say

  6. You

After you’ve gotten into a charged situation it’s very hard to change the context of a discussion, but it can be done.

But the place, Other Person, and what they say are entirely outside your control as long as you’re in the same discussion.

Meanwhile, you have influence but not control over what you say and yourself.

All this makes it very tricky just as a baseline to get across what you want to say. It’s easy to get distracted, or miss a point, or be neurodivergent in a complicating way.

So it’s important to have your house in order as much as you can before you start a discussion.

That’s gonna be a moving target for a lot of people but it’s still the way to approach it.

When I said, “This isn’t easy” what I meant was you’ve kinda got to put in a lot of work before getting into a serious discussion before you can do well.

Shit like therapy, knowing a bunch of relevant crap, maintaining a contemplative practice, etc.

Oh, and absolutely everything is gated by the quality of your attention. So if you’re tired or hungry or having a bad day or otherwise not working smoothly… well, you get the idea.

On top of all that, you’ll need a toolkit to analyze what the other person is saying like critical thinking skills or subject matter expertise.

To cap it off you need to maintain some kind of good faith, where you’re trying to have an honest and fair discussion without ulterior motives.

Unless you’re fucking with someone, of course.

As I said, a ton of this is building sufficient soft skills so you can maintain awareness of your inner state while also listening and trying to proactively understand the other person.

And that’s without discussing awareness of bias, media, narratives, and many other factors.

I’m about to have people outside waiting to pick me up so we’re going to have to close out for today.

Before we go I want to share a few of my active tools for having better conversations.

  1. If you react harshly to someone’s comment, ask them to define or clarify something before tearing into them. Sometimes they’ll turn out to be decent people and if not, they’ll almost definitely make a bigger fool of themselves.

  2. Avoid Wicked Terms which are words that have multiple conflicting meanings. values, God, capitalism, money, etc. If you can’t avoid them, ask for clarification.

  3. Try to imagine what the situation you’re in looks like from the other side or to observers.

  4. If you can, try and get a sense for the history of the ideas the other person is expressing. New ideas are rare. Where did these come from? Who promoted them? What effects have they had?

That’s a taste for part three.

Again, sorry about this being slapdash but that seems to be what I’m doing now.

See you again soon.