The World Is Too Complex for Easy Certainty

I was talking recently with "Michael", a new bar-exam finisher, soon-to-be esquire, when he said something that changed the way I think about uncertainty.

Michael also coaches people preparing for the LSAT.​

We were talking about how students judge their own performance, and he told me that one mistake students sometimes make is feeling too confident about how well they did.

That sounded strange to me.

Isn’t confidence what you want?

If you know the material, shouldn’t you know when you got the answer right?

Sometimes.

But Michael described a different problem.

On an easier question, the best answer may stand out clearly from the alternatives.

But difficult questions are difficult for a reason.

Several choices may initially look plausible.

Now you are not separating the right answer from nonsense.

You are separating the best answer from the almost-right answer.

And suddenly one of the most dangerous thoughts you can have is:

Because maybe it was obvious.

Or maybe you simply did not see the distinction the question was testing.

Maybe there was an assumption you never noticed.

Maybe you imported information the question never actually gave you.

Maybe two answers seemed equivalent because you did not appreciate the subtle difference between them.

Here is the part that stuck with me:

You might not know what you missed.

You do not merely lack information.

You may lack awareness that there is information missing at all.

The Problem With What We Don’t Know

There are things I know.

There are things I know I do not know.

Those are relatively easy to deal with.

If I know I do not understand tax law, I can ask an accountant.

If I know I do not understand a particular BJJ position, I can ask my instructor.

If I know I do not know how a machine works, I can find somebody who does.

The harder problem is what I do not know I do not know.

Because I cannot ask a question about something I do not even realize exists.

And human beings seem remarkably good at filling those empty spaces.

We call it:

• experience;
• common sense;
• intuition;
• what everybody knows;
• obviously.

Sometimes those are useful shortcuts.

But sometimes what happens is:

I do not know.

I do not realize I do not know.

So I assume.

Then I forget that I assumed.

And eventually the assumption becomes something I know.

UNKNOWN → ASSUMPTION → BELIEF → CERTAINTY

That is a dangerous progression.

Not because assumptions are always wrong.

Because once an assumption achieves the status of a fact in my head, I stop looking for evidence.

I stop asking questions.

I already know.

We Have to Simplify

The answer cannot be:

We would become useless.

Reality contains more variables than any of us can hold in our heads.

We have to simplify.

A map is useful precisely because it leaves things out.

If a road map included every tree, crack in the pavement, drainage pipe, electrical conduit, sewer line, insect, building detail, and person standing along the route, it would become useless for driving.

The problem is not that the map leaves things out.

The problem begins when I confuse the map with the territory.

My mental model of the world is also a map.

It has to leave things out.

The danger is forgetting that it does.

That is when simplification becomes simplistic.

Simple can be the product of depth. Simplistic is different.

Simplistic means important parts of reality have been left out, whether because they were inconvenient or because I never noticed them.

A simple answer says:

“After considering the complexity, this is the principle that matters most.”

A simplistic answer says:

“I left out enough of the complexity that the answer became easy.”

Construction is full of simple principles.

• Turn the power off.
• Lock it out.
• Test before touching.

Simple.

Life-preserving.

Martial arts has them too.

• Protect your neck.
• Keep your base.
• Control the inside position.
• Breathe.

Again:

Simple.

But those principles sit on top of enormous complexity.

“Protect your neck” sounds simple after thousands of people have spent generations discovering all the complicated ways someone can attack it.

The problem isn’t that we simplify reality.

We have to.

The problem is forgetting that the simplified model in our head is not reality itself.

Then We Started Talking About Elections

Somewhere in our conversation, Michael and I started talking about elections.

I told him that even with local elections, I frequently do not feel as confident as I think I should.

These are not always giant national contests with international consequences.

Sometimes these are people running for offices relatively close to home.

And I look at the candidates and think:

I am not sure.

One person looks stronger in one area.

The other seems stronger somewhere else.

One policy sounds good until I wonder what it costs.

Another sounds bad until I understand the problem it is trying to solve.

A candidate may promise something I want, but I may not understand whether that office even has the authority to deliver it.

There are incentives I cannot see.

Institutional limitations I do not understand.

Consequences I have not considered.

People I have never spoken with who will experience the decision differently than I will.

I told Michael I found this uncertainty frustrating.

His reaction was interesting.

Essentially:

Maybe that is a good thing.

Then he connected it back to the LSAT.

If you believe every hard question should have one answer that instantly looks perfect while every alternative looks ridiculous, maybe you have misunderstood what makes the question difficult.

Maybe life works like that sometimes.

Not because there is no better answer.

But because the better answer may be sitting next to an almost-right answer.

And telling the difference requires more than confidence.

It requires discernment.

The Seduction of “Obviously”

The word I have become increasingly suspicious of is:

Obviously.

Obviously this candidate is better.

Obviously management should do this.

Obviously the customer is wrong.

Obviously the owner is greedy.

Obviously the employee is lazy.

Obviously the student is not trying.

Obviously this business idea will work.

Obviously this strategy failed because of that one thing.

Maybe.

But I am starting to ask another question:

What would I need not to be seeing for this to look this simple?

That question fits almost everything I have been working on lately.

Because the problem is not merely:

What don’t I know?

There is another level.

What don’t I know that I don’t know?

• What variable have I never considered?
• What assumption am I treating as evidence?
• What question have I never thought to ask?
• Who experiences this problem from a position I have never occupied?
• What happens two moves after the solution I am proposing?

That does not make my first answer wrong.

It means my first answer has not yet earned certainty.

Confidence Is Not Evidence

We often experience confidence as proof.

Someone speaks decisively.

They have a clean explanation.

No hesitation.

No qualifications.

No maybe.

No it depends.

No unanswered questions.

That sounds like competence.

And sometimes it is.

But confidence tells me one thing:

How certain the person feels.

It does not tell me:

How accurate they are.

Those are different measurements.

I have been confidently wrong.

Most people have.

More interestingly, sometimes the person who understands the problem better sounds less confident.

Not because they know less.

Because they see more.

They notice the exception.

They see the dependency.

They understand the tradeoff.

They see the second-order consequence.

They recognize the missing information.

They know where the model gets fuzzy.

From the outside, that can look like uncertainty.

From the inside, it may be increasing precision.

Sometimes uncertainty is not confusion. It is respect for the complexity of the question.

Expertise Can Make the Answer Longer Before It Makes It Simple Again

At the beginning, I might say:

“That’s the answer.”

Then I learn more.

“That’s probably the answer.”

Then:

“That’s the answer if this assumption is true.”

Then:

“That solves this part of the problem but may create another problem over here.”

Then:

“I need to know more.”

It can feel as though learning has made me less capable.

The answer was so simple before.

Now I have:

• caveats;
• conditions;
• tradeoffs;
• dependencies;
• unanswered questions.

But maybe what happened is that my original certainty was cheap.

I did not know enough to know what was missing.

The world did not suddenly become complex. I finally noticed that it already was.

But Uncertainty Can Become Its Own Excuse

There is another trap here.

If uncertainty sounds intelligent, I can hide inside it.

“I need more information.”

“It’s complicated.”

“There are too many variables.”

“I’m still studying it.”

At some point, that becomes another form of avoidance.

We rarely get complete information.

Eventually I still have to decide.

• Vote.
• Hire.
• Fire.
• Start.
• Stop.
• Invest.
• Leave.
• Stay.
• Speak.
• Remain quiet.

The goal cannot be:

Know everything before acting.

That is impossible.

The better goal is:

• Know what I can.
• Identify what I cannot.
• Expose as many assumptions as possible.
• Ask the question most likely to change the decision.
• Act on the best model currently available.
• Stay willing to update it.

That is not the same as pretending uncertainty disappeared.

It is uncertainty with a spine.

⚔ The Dojo Drill

Take one thing you currently feel strongly certain about.

Not something trivial.

Pick something where the decision matters.

Then divide a page into four sections.

I. What I Know?

What can I actually support with evidence?

II. What I Think?

What is my current interpretation?

III. What I Am Assuming?

What have I filled in without enough evidence?

IV. What I Don’t Know?

What questions am I already aware remain unanswered?

Then add one more section.

V. What Might I Not Know That I Don’t Know?

You cannot answer that directly.

That is the point.

Instead ask:

• Who sees this from a position I have never occupied?
• What would an intelligent person who disagrees with me notice?
• What variable might I be leaving out?
• What second-order effect have I not considered?
• What am I calling obvious?
• Which of my facts are actually assumptions?
• What answer is almost right?
• What evidence would change my mind?
• What question could change the next meaningful decision?

Then decide.

Do not wait forever.

Just make the decision knowing the map is not the territory.

Respect the Complexity Without Worshipping It

What Michael gave me in that conversation was a different way to think about uncertainty.

I had often treated uncertainty as a problem.

Something I needed to eliminate.

Maybe sometimes it is.

But sometimes uncertainty appears because I finally respect the complexity of the question.

I see enough to know there may be something I am missing.

I notice that the second answer is almost right.

I see that the choice has a tradeoff.

I realize another person is standing somewhere I have never stood.

And I become a little less interested in proving that my first answer was correct.

I become more interested in asking:

• What am I assuming?
• What am I not seeing?
• What could change my mind?

Then I still make a decision.

That may be the discipline.

Not endless doubt.

Not blind confidence.

Something between them.

I know enough to act, while knowing my model may still be wrong.

And I remain curious enough to notice when reality starts telling me that my model needs to change.

The world is complicated enough without me making it worse by confusing my assumptions with facts.

Sometimes the answer really is simple.

But before I call it obvious, I want to ask one more question:

What might I not know that I don’t know?

📚 Leader’s Library

​A Tale of Two Cities by Charles Dickens​

Why?

Dickens begins by describing a world filled with contradictions:

• Wisdom and foolishness
• Belief and disbelief
• Light and darkness
• Hope and despair

He was writing about the turmoil surrounding the French Revolution, but that opening survives because human beings keep discovering the same truth:

An age can contain extraordinary progress and extraordinary danger simultaneously.

That is worth remembering whenever somebody tells you that everything is getting worse.

Or everything is getting better.

Usually, reality is more complicated.

It is often both.

And leadership begins with learning to see both clearly.

P.S. Know a martial arts gym owner who’s stressed about money or student numbers?

Do them a favor: send them to The Leader's Dōjō, my website where I help owners get more students and keep them longer with simple systems.

One forward from you could change their gym: The Leader's Dōjō​

Chuck