Caesar said:  “The true general’s duty is to secure victory as much by strategy as by the sword.”  Napoleon said:  “Nothing is attained in war except by calculation.  During a campaign whatever is not profoundly considered in all its details is without result.”

Thinking well lessens chance.  A simple, elegant relationship exists between thinking and chance:  the better you think, the less you leave to chance.  Months before a campaign, Napoleon would devise a master plan based on the forces and propensities of his opponent and the “worst conceivable situation.”  He would then devise alternative plans — and continue to do so well into the campaign.  Indeed, much of thinking is simply this:  a consideration of alternatives.

Some of the elements of thinking well:


Nothing is as critical to thinking as is questioning.  Seek far more to formulate questions than to arrive at answers:  answers will come with time and thought.  Hold a Socratic dialogue with yourself. One of the better questions is a quite simple one:  why.


One of Napoleon’s assistants tells us that, early in the Italian campaign of 1800, Napoleon lay on the floor, pushing pins into maps, and said, “I shall fight him here— on the plain of the Scrivia.” Napoleon considered all that the Austrian General Melas might do, and eliminated each in turn.  On June 14, Napoleon met Melas on the field of Marengo, which lies by the river Scrivia.

The Prussian military historian Carl von Clausewitz observed that nothing so lessens our self-confidence as that which we do not anticipate.

Draw Distinctions

How Caesar bound a Gallic tribe to Rome depended on the tribe itself; while he installed kings in some, he strengthened the aristocracy against the monarch in others.  Be leery of terms:  there may be wild variation within any group of people or objects designated by a single term.  We speak of the Pompeians — but the Pompeians were a factious group of optimates, equites, the urban and rustic poor, Gauls and Germans, Orientals and North Africans.

Adapt Your Strategies and Tactics to the Context

You must continually alter your strategies and tactics to fit alterations in the context, must continually conceive afresh.  Napoleon said:  “A great general must say several times a day to himself, ‘What should I do if the enemy appeared in my front, or on my right or left flank?’  If he finds it difficult to answer such questions, he is not in a good position, or all is not as it should be, and he must alter it.”

Think Over Time

Alan Kay, Apple’s resident “thinker” in its early days, said:  “A different point of view is worth 80 IQ points.”  So, too, is considering a thing over time.  Intelligence is partly a function of time:  we are far more intelligent over the long term than the short.

We now consider volition, which is quite as critical in fighting as is thinking.  Richelieu said, “I place the will on a level with reason.”  Or, as Napoleon put it, “The base must equal the height.”

Be Self-Reliant

Time and again, Caesar’s officers and men would beseech him to do this or that; he would consider their requests and then do what he thought best.  In contrast, Pompey would often do what others asked him to do, though he disagreed with them — and this in spite of his frequently saying that a doctor should never follow the advice of his patient.


Address each task as Plutarch said a certain Roman tribune did, “as if it were the only one.”  When the brain is required to do two complex tasks at once, it applies only half as many voxels, or units of brain tissue, to each as it would were it to do each task in turn.  Caesar could simultaneously dictate four important letters to his scribes, and perhaps seven unimportant ones; Napoleon could simultaneously dictate five memos to five secretaries.


Learning is the foundation of thinking:  you simply cannot think about that which you do not know.

Because the world is a complex system, and because all intelligence is of a kind, you must have help in seeing the world clearly, in understanding it.  Learning helps you to be versatile, to be enterprising and resourceful, because it gives you so very much on which to draw.

Early in his reign, Napoleon knew little of administration, finance, or legislation.  To learn about these things, he would call meetings of the State Council, listen to the reports of his ministers, and question both the ministers and those who had worked on the reports.  “From report to report,” a historian said, “he underwent such changes that his ministers failed to recognise him.  During the first report it still was possible to deceive him, during the second it was harder, during the third — dangerous.”

While at Harvard, Bill Gates read countless books on corporate law, finance, and programming.  A Microsoft CFO once conceded that Gates knew more about finance than he did, a Microsoft General Counsel that he knew more about law, and a Microsoft programmer that he knew more about programming.

Nothing so impedes learning as does thinking you know.  Thoreau said:  “Humility, like darkness, reveals the heavenly lights.”

Nothing, said Socrates, is so critical as knowing what you do not know.  When Plato’s half-brother Glaucon proposed entering politics, Socrates asked him a series of questions:  What were the sources of Athen’s revenue?  What were its income and expenditure?  Its naval and military strength?  The state of its garrisons?  How dependent was the city on imports?  Glaucon could answer none of these.  Apply the Socratic method to yourself; show yourself that, whereas you thought you knew a certain thing, you do not.

Things ruinous to thinking, to seeing clearly:

Selfishness:  In his Analects, Confucius says, “Nothing so distorts judgment as does self-interest.”  Selfishness limits how much you walk round an object; you peer at it from one point only.

Persisting in a view:  Few things warp perception quite so much as persisting in a certain view simply because you have always held it.  A Microsoft programmer said of Gates:  “If he really believed in something, he would have this intense zeal and support it and push it through the organization and talk it up, and whenever he met with people talk about how great it was.  But if that particular thing was no longer great, he’d walk away from it and it was forgotten.”

Not acknowledging your mistakes:  On the eve of the Roman civil war, Pompey was slow to act:  why?  The writer Montesquieu theorized that “what harmed Pompey most was the shame he felt on reflecting that he had lacked foresight when he helped Caesar to power.  He…failed to go on to the defensive because he did not want to have to admit that he had put himself in danger.”  By refusing to admit his mistake, Pompey made it far worse.

Emotionalism:  Caesar criticized the Gauls as impulsive, fickle, and emotional and felt their being so weakened them greatly.  “In the [Gallic] towns,” he writes, “a crowd surrounds traders and forces them to declare every place they have come from and every matter they learned there.  These facts and rumors often prompt them to take decisions on matters of great importance, which they are instantly made to think better of.  For they are slaves to vacillating rumors, and most men give them answers made up to suit Gallic wishes.”

Panic:  No matter how much is riding on a fight, or how tempestuous or hopeless the situation, you must remain calm.  Panic is ruinous to reason and resolve.  Knowing you have planned, and thus thought, well will help you to remain calm.  In the most desperate situations, when all seemed lost, Caesar would be perfectly serene, even cheerful.

Not seeing reality:  Richelieu had a certain enemy, Berulle.  As a young man, Berulle was so little of this world that he could not distinguish one coin from another and had the administration of his estates taken from him by his mother.  Berulle’s great dream was to unite the Christian world; he achieved nothing.

The historian Theodor Mommsen said, “Caesar stood aloof from all ideology and everything fanciful.”  The historian Christian Meier said that “Caesar’s risk-taking was nourished by the experience of how little resistance reality often offered if one took a firm grip on the facts of a situation.”