Lessons in Courage and Caution

Allegedly, Alexander approached Diogenes, who was lying down, enjoying the summer air, and stood over him and asked what he, the most powerful man in the world, might be able to do for this notoriously poor man. Diogenes replied …

Source: Ego is the Enemy

The world has a habit of lionizing conquerors. We worship heroes who make their mark in history through indomitable will and courage. Who somehow achieved greatness without ever thirsting for personal glory. That is rarely the case.

Often children, find role models in superheroes. As a child, I was fascinated by Alexander. His heroic conquests and achievements appealed to me. I used to send emails with the signature, “Long live Alexander the Great!”. Not kidding.

However, by creating gods out of men, we conveniently forget their rough edges, their betrayals, their failures, the legions they laid waste to.

So I write this post for the ambitious. Not as a discourse or a sermon. But merely reflecting on a life that burned brightly, but unfortunately also fast.


How often do most of us face 1:10 odds of victory. Or 1:5?

Alexander’s army regularly took down Persian armies which outnumbered them 1 to 25. Alexander never lost a battle in his life despite being outnumbered every time.

It’s easy to discount this as an inborn talent for strategy. But Alexander had this ability to look at the trickiest problem with a lion’s snarl. During the siege of Tyre, Alexander built a bridge to reach the island town only to have it blown apart. He built a navy, only to have its ships burned down. Alexander was advised to ignore the town as an amphibious assault seemed suicidal. He saw otherwise. After months of ill-timed weather, assault by fire arrows, Alexander’s army reached the gates and conquered the city. The siege sealed his reputation as undefeatable and brought down most enemies simply by fear.

This ability to separate emotions from the decision-making process was markedly different from that of Persian ‘crazy-king’ Xerxes. When Xerxes’s bridge collapsed due to a flood, he asked his soldiers to stab the river and spray salt over it’s ‘wounds’.

“Your master lays this punishment upon you for injuring him,” he said. Oh, and he cut off the hands of the engineers who built the bridge.  That’s bat-shit crazy and thankfully, rare.

(Source: Ego is the Enemy)


Nearly all men can stand adversity, but if you want to test a man’s character, give him power.

– Abraham Lincoln

At the Battle of the Granicus, Alexander had his life saved by Cleitus. Cleitus was supposedly a childhood friend of Alexander and regularly rode into battle with him.

At a dinner party after conquering Persia, Creitus criticized Alexander for having adopted Persian culture and clothes. In a fit of rage, a drunk Alexander drove a spear into Creitus and took his life.

While we might dismiss this as an unfortunate incident that occurred while unconscious, it is important to determine its root cause. Alexander, like any highly competitive individual, swung between periods of intense drive and lazy merriness. Often the risk of pursuing something with intensity is that once you lose your purpose, you slow down and inertia takes over. It’s like entropy. High highs’ will be compensated by low lows’. And in these lows, megalomania and ego take hold.

There are countless other tales of obsession in Alexander’s life that drove him to do deeply immoral things.

Probably the greatest lesson here would be to set out on our campaigns dispassionately. For the young and ambitious, stoicism holds many lessons here.

Reading biographies of conquerors is the most efficient way of learning lessons in conquest and compassion for the ambitious.  Save yourself decades of anguish by spending just a few hours reading.

Oh, and what did Diogenes have to say to Alexander.

“Stop blocking the sun”

Embark on your conquest only if you care about it. Because at the end of the day, no one else does.


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