If you’ve followed me on social media for long, you’ll note I’m very proactive about engaging in conversations with people of opposing views.

(Note this has a companion Twitter thread here)

I consider this one of the most important tools for learning in my toolbox.
This isn’t because a single response tweet or comment can tell you everything you need to know all at once, but it can’t often give you a critical clue you needed that you were off course. But there’s a problem… especially these days.

Often people associate their opinions with their identity. I won’t be the first to observe this is a common, tribal instinct. And indeed, there are many, many studies on this. We enjoy a sense of belonging and togetherness.

Unfortunately, this can likewise manifest opposition and contempt toward other groups who associate around a different set of opinions that they draw collective identity from. An obvious example of this are political parties. But we now also see this commonly with nutrition.

And herein is the problem.

Crossing Party Lines

Imagine you (as an individual) want to have an intellectual conversation with someone from a different “tribe” to better understand where they (as an individual) are coming from. You have two major things working against you…

For one, they may already be hostile toward you given you inadvertently represent the last several people before you from your “tribe” that were hostile toward them. Their defenses are up.

For two, many simply won’t trust in your sincerity to have a fruitful conversation.

Changing one’s opinions on the above two can take a lot of work, but I think the cost/benefit has netted a positive for me overall. Sure, many people simply aren’t interested in strictly rational and non-personal conversation no matter how much you try to make it happen.

But for what it’s worth, I think you’d be surprised how many people will engage in such conversations if you can build trust and rapport with them.
I now have many, many good friends with opinions very different than mine, but for whom each of us has influenced each other.

I think the key is to continue being courteous well past the initial barbs thrown your way and, as they say, “kill them with kindness”.

Let me be blunt, doing this is very challenging. We aren’t built that way. We want to defend ourselves and fight back.

Economics of Self-control

While defensiveness can be appropriate in many cases, one of the biggest life lessons I’ve learned is that much of the time it is simply unproductive. It typically just keeps conflict alive or escalates it to new levels. Often showing persistent generosity deescalates.

One of the most common comments I get from friends in DMs: “Why are you talking/debating with ______??? They are a _______ and not worth a moment of your time!” In some cases this will prove true, in others false — but I don’t always know until a later point.

In business there’s a term called “cost of sale”. For example, if 100 spam mailers go out and only one person responds — but the margin on that one response exceeds the cost of all those mailers, then the “cost of 1 sale” was 100 mailers. Sorry, that’s how spam works, of course.

Thus, the key question is whether the gain of insight from 1 person with differing views and many successive, productive conversations is worth, say, 5 attempts with others that ultimately failed to do likewise? Right now, I’d say yes, it seems to be the case.

But more than that, I think it’s about maintaining the constant, unrelenting habit of challenging core beliefs. Some of my strongest held opinions came from failing to defend an opposing opinion I had at the time. I had to relent and adopt the view that made greater sense.

Sticking to the Arguments

With all that said, it’s important to keep one simple rule in mind and continually affirm with every conversation:

-> Where expressing an opposing opinion – one should strive to be attacking the argument they disagree with, not the person presenting it.

I do my best to practice this every day in every conversation, tweet, and blog post — particularly where addressing people directly. (As an aside, I’m definitely not saying I have 100% success rate by any means. I always feel I can do better.)

And for what it is worth, I often find people can follow my lead and do likewise when I’m chatting with them in this manner. Again, we’re social creatures. So in a way, you’re starting an instant “tribe” of rational discussion you both can feel belonging with in the moment.

However, sometimes it doesn’t work in the beginning or even develops problems later on. But having that compass built in at all times helps keep me aware as to how much these conversations are guided by analysis of the assertions over judgements of the person making them.

At a certain point you have to recognize there is much more of a problem in trying to overcome this perception than is worth engaging in. And by the way, this applies to *all* the people in your life: work colleagues, long time friends, romantic relationships, etc.

Which is why it’s easy to test by simply asking if each person can get through a conversation without ridicule, personal attacks, biting sarcasm, and any number of other expressions of negative judgement of the other person. If it seems persistent- probably need to let go.

Final Thought

This may seem like a lot of work. It is. It takes a lot of energy to push back from those deeper instincts.

But I can vouch it has been paying very big dividends in my journey thus far and I can’t imagine it any other way.