Two cool concepts for intellectual humility

If there’s one thing all the world’s ancient wisdom traditions agree on – from the Bible to the Tao Te Ching – it is the power of intellectual humility.  Meekly embracing the limitations of your understanding is, paradoxically, what grants true understanding.  Surrendering your certainty takes you further than clinging on to it.

This is a key theme in a lot of my strategy spiel – most notably my little ebook Effort is the Enemy, which you can download free here.

The basic reason is that effective strategies emerge from finding the way that things naturally “want to be”, and rolling with it – rather than the more common practice of insisting on things being the way you want them to be.

However such humility is easier said than done.  Thus I wanted to dedicate this essay to two sort of “parables” which I think help get you into the intellectually humble mindset.

Frankly they’re just quite cool things really, so feel free to enjoy them for their own sake – with or without the moral lesson attached.


Some of you will have heard of this already, but I’m guessing / hoping that the majority won’t.

The Monty Hall Problem is a probability puzzle named after the host of the gameshow Let’s Make a Deal, thanks to the similarity it has with that format.  It goes something like this:

Imagine you’re on a gameshow, and you’re presented with three doors.  Behind two there are nothing, but behind one there’s a car.  Your job is simply to pick a door, and if it has the car behind it, you win.  So you pick a door, say number 1.  Now before revealing whether you’ve won or not, the host, Monty, decides to ramp up the tension, and opens one of the two remaining doors (door 2 say) to show there’s nothing behind it.  Now you know that the car must be behind either your door, or door 3.  He then says “OK, last chance, do you want to change your mind, and switch doors?”.

The question of the problem is: should you?  Is it to your advantage to switch?  Or does it make no difference?

Have a moment to think.

Now unless you’re either 1) already familiar with this problem, 2) a genius, or 3) are second guessing me because you know I’ve picked this story for a reason, then I’m certain your conclusion will be “no, there is no reason to switch doors”.  The car is just as likely to be behind your door as the one left over.  It’s 50/50.

If this is your view you’re in good company, as over 1000 PHDs and mathematicians wrote to Parade magazine to argue this when they published the riddle in 1975.  They were responding to the differing opinion of Marilyn vos Savant, the Guinness World Record holder for the “highest IQ in history”, who insisted that you should switch doors, as the other door has a higher probability of concealing the car than yours.

And indeed she was correct: your door has a 1 in 3 chance of holding the car, whilst the one Monty chose not to open has a 2 in 3 chance.

The reason this problem is so great is because it’s fiercely, almost indecently counter-intuitive.  It’s extremely hard to wrap your head around why on earth the probability of each of the remaining doors wouldn’t be equal.  As a result you are likely to be certain your choice not to switch is correct, even when you’ve been told you’re wrong.  Indeed Paul Erdos, one of the greatest mathematicians in history, refused to believe this until he was shown a simulation of the problem, whereby indeed the other door was shown to hold the car 66% of the time.

If you want to know why this is, the basic reason is because the door Monty chooses not to open has been somewhat “endorsed” by him as possibly holding the car, and thus is the more favourable option.  You have a hint that door might be the winner, whilst you have no such hint for your door since he couldn’t open it due to you picking it.  Thus the odds of your door holding the car remain stuck on the odds you picked it at (1 in 3), whilst the remaining door has new, better odds (2 in 3).

If you’re still not getting it, think of it like this: imagine there were 1000 doors, rather than 3.  Again, you are asked to pick one.  And again, Monty builds the tension by opening all remaining doors other than yours and one other – which in this case means that he has to open 998 doors to leave those two.  In such a scenario you’d be like “wow, that door he left almost certainly has the car behind it, since my pick was almost certainly wrong – I’d better switch!”.  It would be a no brainer.

Well, the 3 door version is exactly the same, only with less extreme odds.

What we can learn from the Monty Hall Problem, I think, is just how easy it is for us to be certain of things where we are actually totally wrong.  It is, ultimately, a very simple construct – and yet even then we can be wildly misled.  So just imagine how much more pronounced the effect must be in the messiness of the real world.


Of course, the nice thing about the Monty Hall Problem is that at least it does have a definitive right answer.  When we’re navigating reality however, we have to accept that such cut and dried solutions are very much the exception not the rule.

Indeed, I would go so far as to state that most debates people have with each other arise not because one person is right, and the other wrong – but rather because both people are right, and they just don’t understand that their views are actually compatible.

Today we don’t get this, but I’ll tell you who did: the Xhosa people of South Africa.

I think I may have mentioned this before, but it bears repeating.  Hundreds of years ago, when the Xhosa were having a debate political amongst themselves, they had a curious code of conduct.  Essentially nobody was allowed to make a point until they had first laid out the argument of their opponent to the opponent’s satisfaction.  By doing this they proved that they properly and correctly understood what they were arguing against, and thus were able to make counterpoints of real substance.  The process would then be repeated on the other side, thus building ever deeper understanding, and eventually some sort of holistic consensus.

What the Xhosa understood was the simple but again counter-intuitive fact that you have no right to argue against a point of view that you don’t understand in the first place.

The majority of our contemporary debate – not just political, but in all fields – is, I suggest, simply a matter of two parties attacking the imagined position of their opponent, rather than the actual position.  Naturally this results in ever greater division, rather than understanding, along with hopelessly inadequate “solutions”.

The term for this approach is of course to create a “straw man” of your opponent’s argument.  Typically we assume this is something that’s done deliberately and maliciously, but in truth I think it’s actually the accidental default setting.  The opposite – the Xhosa approach – is sometimes called “steel manning”, in contrast to this.

Now of course, I understand why we don’t tend to take the approach of the Xhosa: it would take a bloody long time.  Interestingly I heard from someone that on Joe Rogan’s podcast they floated the idea of a debate between two sides of a particular Covid-related issue.  One of the scientists in question said that wouldn’t be possible, because to do it robustly would take a week, not just a couple of hours – to which Rogan responded “OK fine, it takes a week, why not?”.  Credit to him for that.

This made me wonder just how many important issues get mishandled simply because addressing them in a mature Xhosa style would take “too long”.

Regardless, the lesson here is a simple one: when you find yourself in a disagreement with someone, remember that they are almost certainly right in their analysis.  And so are you.  It’s simply that your points of focus have parted ways multiple levels beneath the superficial surface of the debate.  Were you to peel back the layers, in open hearted good faith, you would eventually find that point of departure, and thus reach full understanding.

So, pretty cool ideas I think.  And I promise you, they are not theoretical.  I’ve found there to be a strong correlation between the intellectual humility of founders I’ve worked with, and their effectiveness.  And I dare say that even some of the notoriously “arrogant” founders of legend were merely arrogant in style, but humble in substance.

Although, of course, I could be wrong!

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