Desperation Resides in the Strategist’s Toolkit

Sink your ships, embrace urgency, and face the present. When things get tough and your back is up against a wall, desperation will give you energy and power; so let it propel you to victory.

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Ted Williams Desperation

Who is your worst enemy? The answer, simply put, is you.

And that’s because we often waste time thinking of the future rather than engaging in the here and now.

There is nothing urgent to us, and so we are only half-involved in what we do.

As a result, we get nowhere, and then we ask ourselves what went wrong, and where did it go wrong.

And the reason for this is that we have so little on the line.

But there is one way to change this – and that is to add a little desperation into your life.

We must turn the situation into one where there is too much at stake to waste time and half-ass it.

You must enter unknown territory and depend on your intelligence, determination, and creativity to see you through.

When you can’t afford to lose, you won’t lose, so put yourself in a situation where your back is against the wall, and you have to fight like hell to come out alive.

By doing so, you will certainly make it out alive.

Sink All Your Ships

In 1504, a Spanish nineteen-year-old named Hernán Cortés gave up his studies in law and decided to set sail for the New World.

First stopping at the island named Santa Domingo, which today makes up the countries of Haiti and the Dominican Republic, he then moved on to Cuba.

Once there, he heard about a place called Mexico that was inhabited by the Aztecs – it was a land teeming with gold and had a splendid capital called Tenochtitlan.

From then on, he would live by just one thought – he would become the conqueror of Mexico and become the first Europe to settle it.

Over the next ten years, he would first become the governor’s secretary, then the king’s treasurer on the island of Cuba.

During that time, he bided his time and waited patiently as his country sent other men to Mexico, although none would succeed, and many wouldn’t even come back alive.

This continued until finally in 1518 the governor of Cuba made Cortés the leader of an expedition to Mexico.

His job was to find out what had happened to the other expeditions, find gold and lay the groundwork for a future conquest to be made by the governor himself.

At first, Cortés was chosen because he seemed easily controllable, but soon the governor would have second thoughts – Cortés was clever, you see, perhaps too much so.

Soon word reached Cortés about the governor’s second thoughts, so he gave the governor no chance to change his mind.

During the middle of the night, he slipped out with eleven ships and headed towards Mexico.

In March of 1519, they landed on Mexico’s east coast, and quickly Cortés went to work.

He founded the town of Veracruz, forged alliances with the local Indian tribes, and then made initial contact with the Aztec emperor whose capital was about 250 miles due west.

But on his ship were some men whom the governor had placed as spies, and who were told to cause trouble should Cortés exceed his authority.

They would accuse him of mismanaging the money, and they accused him of being insane.

Indeed, their claims were certainly plausible, for after all, he intended to conquer an empire of 500,000 with just 500 men.

And why would he want to stay in a place with no basic luxuries, in a place where their wives and children were not present?

Surely, the man must be crazy.

Cortés did what he could to pacify these men – some he bribed; some he kept a close eye on.

Meanwhile, he worked to build a rapport with the other men so their sophistries wouldn’t sway them.

But the situation would boil over when on the night of July 30, Cortés was awoken by a sailor who confessed to being a part of a plot to steal a ship, sail for Cuba, and then tell the governor back in Cuba about Cortés’ ambitions.

Cortés sensed that a decisive moment was upon him.

But while he knew he could easily quash the mutiny, at the same time, he knew there would be others if the root of the issue wasn’t resolved.

Fall of Tenochtitlan (Source: The History Press)
Fall of Tenochtitlan (Source: The History Press)

The root of the issue was that the minds of his men were on gold, their families, or home – anything but on conquering Mexico.

He had to come up with a plan to divert their attention to the important matter at hand.

So, he quickly seized the two ringleaders and had them hanged.

Next, he bribed some men and had them bore holes into the ship, which he then blamed on worms, thus making them unseaworthy.

However, when he ordered them sunk, five hadn’t been damaged enough, so they didn’t sink.

At first, when his fellow sailors found out, they accepted the story, worms were certainly a frequent menace to ships at the time.

Yet, when four of the remaining five were sunk a few days later, the sailors realized that Cortés was behind the whole affair.

When he called a meeting that day, the air of the room was unsurprisingly mutinous.

Sensing the mood, he decided to do away with all subtlety.

He laid it to them straight – he admitted it was him, and yes, he had deliberately done it.

They could hang him, but what would come of it?

They would be leaderless whilst surrounded by hostile Indians and Aztecs.

The only way to get back to Cuba alive was by becoming lords of Mexico.

Consequently, they would have to be unified and fight with utter intensity, otherwise only a terrible death awaited them.

But he did guarantee them one thing, not only would they be successful should they follow him, but the rewards would be all the greater since they were so small in number.

Lastly, he offered any cowards not up to the challenge to take the last ship home – he didn’t want anyone to hold him back.

No one took up the offer, and the last ship was sunk.

Over the next few months, Cortés kept the army away from Veracruz and the coast.

As the reality of their situation dawned on them, their self-interest gradually dwindled away along with their greed.

And so, two years later, with the help of their Indian allies, the conquistadors laid siege to the heart of the Aztec empire, Tenochtitlan, and conquered Mexico.

Analysis

During the night of the conspiracy, Cortés had to think quickly.

He had to understand what the root of the problems he faced was.

It wasn’t the governor’s spies, nor was it the terrible odds against him.

The problem was that his men were divided both in mind and at heart.

Rather than thinking about the most important matter, the conquest of Mexico, they thought of home, gold, and their wives.

As a result, those ships were no longer just modes of transportation; no, they represented Cuba, the ability to leave, and all their other desires.

For them, the ships were their backup, something to fall back on when things got ugly.

And because they had a backup, they didn’t put all their energy into the campaign ahead.

So Cortés’ decision was simply to destroy the ships, in order to destroy their only other backup.

This sense of urgency that Cortés hoped to cultivate in his men comes from a powerful connection with the present.

Rather than on the future or on any potential rescue attempt, they had to face the issue at hand.

Succeed or perish, that was their only two options.

People you come across with this sense of urgency often seem much more intimidating, because they are focusing so intensely, they seem much more powerful than they really are.

So when Cortés displayed this urgency to his men, he suddenly looked as though he had the backing of a much larger force.

Much in the same way Cortés did, you must also find the root of your problem.

Often it is not someone else or the situation in front of you.

Rather it is you because it is you who is simply not desperate enough.

Instead of intensely focusing on the situation in front of you, you rely on an escape route ready if things go awry.

And so, instead of giving it your all, you put only half your energy in.

Just as Cortés’ men saw the ships as a blessing, you may also believe these other options you have is a blessing; whether that may be a wealthy relative willing to buy you out, or a comfortable job to fall back on.

In reality, though, this is all a curse.

Sometimes you must sink all your ships and leave yourself no choice except to succeed.

By making the sinking of your ships as real as possible, you get rid of your safety net.

When you have nothing to lose, you become desperate, and when you become desperate, you become powerful.

Time Isn’t Limitless

At the age of just twenty-four, Fyodor Dostoevsky shook the Russian literary world with his first novel Poor Folk (1845).

And as a result, he gained newfound fame in St Petersburg high society.

But there was something to him that was empty about his success.

He soon drifted into left-wing politics and joined a few radical groups, one of which centered on a certain Mikhail Petrashevsky.

Three years later revolution broke out across Europe, and, excited by these events, many radical groups spoke of inciting their very own revolution.

However, agents of Czar Nicholas I had been documenting what was happening at Petrashevsky’s house.

Dostoevsky, especially, was vocal about measures such as freeing the serfs, and so, in 1849, he along with twenty-three members of the Petrashevsky Circle were arrested.

It was after eight months of languishing in jail, they were finally woken one morning and were told they were to hear their sentences.

Usually, the average punishment would be a few months in exile, so soon, they hoped, their ordeal would be over.

As they were driven to hear their sentences, they passed through the icy streets of St Petersburg until they finally made it to Semyonovsky Square.

There, they were greeted by a priest, and around them they could see a scaffold with three posts, rows of soldiers, and a pile of coffins ready to take the dead.

“It is not possible they mean to execute us” whispered Dostoevsky as they were marched and placed in front of the scaffolds in two rows.

Next a drumroll sounded, and an officer came out who read their sentences, “All the accused are guilty of intending to overthrow the national order and are therefore condemned to death by firing squad.”

The prisoners were too stunned to speak.

It was at that point that Dostoevsky made a prayer: “If I do not die, if I’m given another chance, my life will seem endless – I will not waste another chance at life again.”

Next, they were given shirts to cover their eyes, and a priest came to read them their last rites and hear their confessions.

The first three were tied to the post, ready to be shot, while Dostoevsky stood in the group right after them.

As the soldiers took aim and put their fingers to the trigger, suddenly a man came riding in with an envelope.

The czar had at the very last second commuted their sentences.

Later that morning Dostoevsky was given his new sentence: he would do four years of hard labor in Siberia, then serve in the army.

Barely affected, he wrote to his brother: “When I look back and think of all the time I squandered in error and idleness… my heart bleeds. Life is a gift…if only youth knew! Now my life will change; now I will be reborn.”

He would receive a few days later ten-pound shackles to be placed on his arms and legs, then he was hurried off to Siberia.

With no writing privileges, he wrote his novels in his head and memorized them.

It was later on during his time in the army he was allowed to start publishing his work.

He would write and write and lose himself in the plot and in his characters’ stories.

Some pitied Dostoevsky for his ordeal but he himself was forever thankful for the experience.

If it weren’t for that night in 1849, he would have idled his life away.

Yet now he could do what he loved most day in and day out.

And he would go on to write literary classics one after another, novels such as Crime and Punishment, The Brothers Karamazov, The Possessed, and more as though each was going to be his last.

Analysis

The czar, it turns out, had already thought of this punishment soon after they were arrested.

He wanted it to be so cruel that they would be completely humiliated and humbled.

Some, as a result of this punishment, actually turned insane due to the events of that day.

But the effect on Dostoevsky was much different: it acted as a reset; a rebirth of a life that had so far been wasted in idleness.

The effect for him, therefore, was permanent, and from then on, he would seek to recreate that moment whenever he got lazy.

His favorite method was to go to a casino and deliberately gamble all his money away.

For him, you see, poverty and death were a sort of symbolic death.

What this did was help him become, unlike any other author or writer around him.

Unlike them, he wrote his novels as though his life literally depended on it.

Death is often hard for us to fathom; it is immense and at the same time scary.

Nor does it help that society is organized to make death invisible.

But what that does is make us run away from the one thing that is guaranteed.

It makes us believe that our time is limitless when it is not, and so we end up living our lives unseriously.

As a warrior, you must aim to turn this dynamic around.

Rather than running away from it, embrace death.

Your days are numbered – that much is inescapable.

So imagine death pressing down on you, that feeling of death being at your heels will make your actions more certain, more forceful, more meaningful.

Death Ground

There are many times we find ourselves lost in our actions – we do this or that, yet everything feels unnecessary, it all feels unurgent.

We have routines that help us avoid the feeling of directionless but at the back of mind we can feel that we can do so much better.

And by constantly going through this cycle every day we waste so much time.

But every now and then something happens that makes us become desperate.

Suddenly we have a new responsibility thrusted on upon, and our whole reality changes.

Or perhaps there is more work to do right before a deadline, so were jump into action in order to make it.

In these instances everything changes, there is no more freedom.

We have to do this; we have to fix that.

In those moments it’s as though we have been jumpstarted into action, and we are full of energy.

And at the end, we marvel at how much work we’ve done and how more alive we feel.

Yet we end up going back into our daily routines, and waste yet more time.

When this urgency goes, we don’t know how to get it back.

Generals throughout history have thought and grappled with this dilemma.

How can the soldiers feel a constant sense of urgency to become more aggressive and urgent?

Some have used crowd-whipping oratory, others may use rewards and punishments as a motivator.

The Chinese strategist Sun-Tzu also thought of this, and the solution he found was to put the soldiers on what he called “death ground”.

This was a situation in which the troops were forced to either die or survive.

This may be having their backs to a mountain or a river, and nothing except the enemy in front of them to fight.

When in these situations, suddenly their urgency would return as they furiously fought for their lives.

This is also what Cortés did when he sunk the ships soon after he arrived in Mexico.

What this tells us is this: the world is ruled by necessity, people only change when they have to, and people become urgent when they feel their lives depend on it in some way.

This very real pressure at your heels makes you feel like you cannot retreat, it makes us feel as though time is running out.

So what do we do?

We either act or face the dire consequences.

So put yourself in a high-stakes situation, put yourself in a psychological “death ground”.

Suddenly you will feel a surge of energy and your mind will sharpen.

Use this trick from time to time – but remember, this is not something to read only, you must act on it.

And in order to help you, below are some practical ways you can incorporate the death ground into your life.

Stake Your Future

In 1937, Lyndon B. Johnson was working as the Texas director of the National Youth Administration.

And it was during his time there that he was faced with a dilemma.

The Texan congressman James Buchanan had just passed away, and his Texan congressional seat was suddenly available.

The thing with these seats is that since the Texan voters are so loyal, these seats were only available once every ten years.

He was already twenty-eight, and he wanted to join Congress by thirty – simply put, he didn’t have 10 years to wait.

But what if it all went wrong?

Not only did he have to face off against other political heavyweights, but it would also be a waste of money and a severe humiliation if he lost.

Nonetheless, Johnson decided to run.

Lyndon B. Johnson's campaign poster. (Source: LBJ Library on X)
Lyndon B. Johnson’s campaign poster. (Source: LBJ Library on X)

And in the next few months he would not just take a stab at it, no, he would stake everything he had on the race.

He would pull every trick in the book; he would shake the hand of every farmer from every backwater, he would do old-style barbecues and even try out those new radio ads.

Day in and day out he would work, and eventually, he would even be hospitalized for exhaustion and appendicitis.

Yet, in one of the great political upsets, he won.

When he decided to stake his future on a single chance put himself on “death ground”, and his body responded with the surge of energy he needed.

Many a time we may be focused on too many things at once, thinking that might have better chances of success.

But all we end up doing is dividing our attention and energy.

Instead, it is more productive to try one daunting and seemingly indomitable challenge where your future is at stake.

Yes, others may even think you are crazy, but when we can’t afford to lose, we don’t lose.

Seize the Initiative

In 19 B.C., a group of senators allied with Pompey issued a decree to Julius Caesar ordering him to disband his forces in Gaul.

Over the years they could feel his power growing and feared that he would want to take over the entire Roman Republic at some point.

At the time, he was in southern Gaul (now in modern-day France) with only 5,000 troops.

The rest of his legions were further north at the time, and it would have been weeks before they could join him.

Yet he had no intention of obeying the order – that would be suicidal.

But nor could he just stay in Gaul and wait for the senators to muster up an army to attack him.

So, in a shocking turn of events, he said, “Let the die be cast”, and quickly crossed the Rubicon, the river that marked the border of Italy.

The Roman Senate (Source: TU Dresden)
The Roman Senate (Source: TU Dresden)

He concentrated his forces and moved with swiftness as he marched upon Rome.

By seizing the initiative, and despite the small amount of troops with him, he struck fear into the hearts of the senators and so they, along with Pompey, fled to Greece.

Rather than taking too long to decide, take the initiative and cross your Rubicon.

Even if you are not ready, sometimes you should just make the most of your resources and take your opponent by surprise.

Once you have committed yourself and there is no turning back, you let your creativity flourish.

Do this often to develop your ability to think and act fast.

Wade into Unchartered Territory

Joan Crawford was signed to the Hollywood studio MGM, and during that time, MGM had been good to her.

But by the early 1940s, she had had enough.

They kept casting her in the same role, and she wanted something new, something challenging.

So in 1943, she did the unthinkable, she left MGM.

Had this not worked out the consequences would have been fatal for her career.

You see, at the time it was the studios that had the power, not the actors.

And so leaving your studio was like leaving your home for the wilderness, it was simply too unpredictable, and hence seemingly unwise.

Indeed, when she signed up for Warner Brothers, she was given the same sorts of mediocre scripts as before.

One after another she rejected them all.

Eventually, on the verge of being fired, she finally got the movie she wanted, Mildred Pierce, in which gave the performance of her life.

She not only resurrected her career with that movie, but she also won the Oscar for Best Actress.

In leaving MGM, Crawford was taking a very big gamble, a gamble that was likely to fail.

But she knew she was at her best when she was challenged and so thrived on risk.

Sometimes it’s good to do away with the old and go for the new.

This may be done with comfortable situations or friendships that hold you back.

Leaving for unknown territory is like risking death, and it will help snap you back to life.

Take on The World

Unlike in other sports, in baseball, there are few outlets for aggression.

This was the problem hitter Ted Williams encountered early on.

Yet it was when he was angry when he felt as though it was him against the world that he played his very best.

Unfortunately, it was hard to stimulate this emotion on the field.

Soon, however, he found a secret weapon – the press.

Whenever he got the chance he railed against the press, and they would be only too happy to return the favour.

He would get into the habit of insulting sportswriters, and they in turn would write scathing paces when there was even a slight drop in his form.

In 1957, the year during which he had a yearlong feud with the paper, he also played his greatest ever season – at the ripe age of forty.

One sportswriter even wrote, “Hate seems to activate his reflexes like adrenaline stimulates the heart. Animosity is his fuel!”

For Williams, the loathing of the press and even the public towards him only fuelled him more.

When they doubted him, when they wanted to see him fail, he used their hatred to power himself to glory.

A fighting spirit needs a little edge, something like anger or hatred to fuel it.

Sometimes, rather than sitting back and letting others get aggressive, you should irate and infuriate them incessantly and deliberately.

When you feel cornered by all the multitudes that hate you, you will fight like hell.

When you fight, your enemies relish your failure.

So use that pressure to make yourself fight harder.

Practice Taking Risks

Of the qualities that made Napoleon perhaps the greatest ever general, there is one that stands out – his boundless energy.

When others worked eight-hour days, he worked eighteen hours or even twenty-four-hour days.

Sometimes for days on end, he would not even sleep.

He would work in the theatre, during lunch, and even during his bath.

He kept an eye on every detail, and he would never tire nor complain.

Napoleon’s endurance was certainly amazing, but there was more to it – he never let himself be satisfied.

When he finished conducting his first ever campaign which was in Italy, he immediately left for a campaign in Egypt.

However, he soon came to loathe how the political power in France was cutting into his authority and thus limiting his gains.

So, he went back to France and conspired to take control.

That being done, he went over to Italy for his second Italian campaign.

And on he went, finding and immersing himself in new challenges.

Sometimes, we are only tired when we are bored.

There is no real challenge facing us, so we respond with mental and physical lethargy.

Napoleon himself said that sometimes death only comes from a lack of energy.

Make taking risks a constant practice, and you’ll find that your body responds aways with a surge of energy.

The risks you keep taking and the challenges you constantly overcome are like momentary deaths which only increase your appreciation for life.

Be Careful

If the feeling of having nothing to lose will propel you, it will also do the same for others.

So you must avoid conflict with such people.

Maybe they are facing terrible conditions, or perhaps are suicidal for some reason.

In any case, they are desperate, and desperate people will risk everything in a fight.

Conversely, attacking an enemy with low morale gives you an advantage.

Perhaps they fight for a cause they know is unjust, or they fight under a leader whom they do not respect.

Such troops are easily discouraged by any setback, so find a way to crush their fighting spirit further.

Always try to lower the enemy’s sense of urgency – let them think they have all the time in the world.

That way, when you suddenly appear at their door, they simply will not be able to resist you.

Do everything to sharpen your fighting spirit, and do everything to blunt theirs.

Footnotes & Further Reading

Greene, Robert. The 33 Strategies of War. Millionaire

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