The Theoretical Should: How To Handle The Know-It-All? - A master-race stick figure telling a normal stick figure "Why don't you do it THIS way?" An arrow from right to left indicates the assumption of the theoretical should on the master race stick figure's part.

I have been getting this a lot lately. Someone I know approaches me and tells me something along these lines:

“Hey! I saw that you have been doing this and that. I know you are a clever guy, but I feel that you are missing the obvious. I think that you should be doing THIS instead, as it is a better way to use your knowledge and skills.”

When I hear something like this, I feel a little attacked and intimidated. But I strive to be as open-minded as I possibly can. So, I muster up the courage and ask the person for further reasoning behind their argument/claim.

Often, I get reasoning along these lines:

“Well, look at ‘x’ who is half as capable as you. They get much better results doing what I suggested.”

This typically makes me roll my eyes. But this “pattern” of events set me thinking. I figured that there is something deeper going on here, which eventually led to this essay. So, here we are.

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The Rolling Eyes

Let me get back to the point where I rolled my eyes. Why exactly did I do that? When I introspected, I recalled that it was due my own internal reasoning. In my head, I thought something along these lines:

“Oh! This person thinks that ‘x’ is half as capable as I am. That reasoning is flawed because I know from experience that it is not the case.

I tried the same approach to solving the problem, and realized that ‘x’ makes hard work seem remarkably simple and easy.”

Now, I know that I am not giving you any specific context about this scenario. But I am pretty sure that most people can relate to this situation. It appears to me that this is a pretty common psychological pattern in human beings.

The Dreaded Know-It-All

It is very tempting for you and me to label my challenger as “The Know-It-All”. But let us pause there for a moment. There once lived a famous Swiss psychoanalyst named Carl Gustav Jung who proposed the notion of “shadow projection”.

The basic idea is this: When a certain trait or behaviour in another person bothers you, it could be because you are denying or suppressing the same trait within yourself.

I tried chasing down scientific proof of this phenomenon and came back empty handed. However, I did find experiments that proved (with double-blind studies) the existence of this phenomenon. In other words, while not every trait that bothers you about someone is projected, at least a few are.

So, giving this possibility the benefit of doubt, I tried to recall and actively monitor my own thoughts and actions that link me to the “know-it-all” pattern. And it turns out that I do in fact feature the same pattern towards others as well. In other words, in more than one occasion, I felt that someone else should do something in a way that I thought was better. I even found my reasoning very convincing.

But from my own experience, I knew that I was probably wrong. So, instead of blaming the “know-it-all” and attacking the person, I chose to attack the underlying problem instead.

The Theoretical Should — A Subtle Pattern

After all these years of introspection, I have come to realise that almost all of my “brilliant” reflections are seldom original. I am human, after all. Someone out there has probably come up with the same reflections and proposed solutions too.

Based on this assumption, I searched for people who have tried to tackle this challenge, and the name “Ray Dalio” and the notion of the “Theoretical Should” came up. Dalio postulates that a “theoretical should” occurs when someone thinks others should be able to do something when they actually have no first-hand experience or knowledge of whether they can.

From my personal experience, even if I have first-hand experience doing something, I could be completely wrong in assuming that someone else “should” be able to execute it as easily/well as me. The reason is that people are different and have their own uniquely different strengths and weaknesses. Who am I to judge what someone else is good at?

So, the lesson seems to be “Beware of the theoretical should!” But we cannot just fear and cower, can we?

How to Handle the Know-It-All and Tackle the Theoretical Should?

I would like to split my solution into two parts. The first part lies in the introduction of this essay. When someone challenged me, I felt attacked and wanted to go into a defensive mode. But I overcame this, and asked my challenger for their reasoning behind their claim.

Recalling that Jung’s projection is not a universal truth but certainly a possibility, there is a slim chance that the constructive criticism from the challenger could have merit. So, it makes sense to me to ask for further reasoning. Based on the reasoning, one could reassess the merit of the challenge/criticism.

The Theoretical Should: How To Handle The Know-It-All? — An illustration showing four stick figures sitting on a tree branch left to right. The left-most stick figure is sawing off the branch. The stick figure next to him says, “Great! Do it exactly how I told you to!”
Skin in the game — Illustrtive art created by the author

As for the second part, I would like to invoke the notion of “skin in the game” from my involvement with financial projects. When Trader A tells Trader B to make a certain trade, a prudent question from Trader B would be:

“If I make the trade, are you willing to commit 75% of the necessary capital?”

In other words, the notion of “skin in the game” filters out the backseat-drivers. If someone tells you to do something, that someone should be willing to not only benefit from their advice but also get punished for it.

To be fair, “skin in the game” does not mean that the criticism has merit by default, but it makes the “should” much less “theoretical.”

Summary

To summarise, I started by dissecting a psychological pattern that involves unsolicited advice from someone acting like a “know-it-all”. After considering Carl Jung’s shadow projection a possibility, I recognized my own “know-it-all” behaviour from introspection and observation.

The Theoretical Should: How To Handle The Know-It-All? — A master-race stick figure telling a normal stick figure “Why don’t you do it THIS way?” An arrow from right to left indicates the assumption of the theoretical should on the master race stick figure’s part.
The Theoretical Should — Illustrative art created by the author

As I was looking for solutions to this psychological challenge, I came across Ray Dalio’s idea of the “theoretical should”, which postulates that assuming others’ abilities and capabilities can often be misleading.

Rather than just passively avoiding the “theoretical should”, my active strategy to tackle it involves two parts:

1. Remain open to criticism, seek further reasoning, and reassess its merit.

2. Introduce “skin in the game”, ensuring that critics are willing to get punished for making wrong-calls.

This approach allows for a healthy exchange of ideas whilst minimizing the pitfalls of the theoretical should. I hope that you will be able to harvest insights from my account to benefit your applications as well.

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