How to Cross the Rubicon
Make up your mind, then fight to the death...
January, 49 BC. Julius Caesar stands at the edge of the Rubicon, staring into the waters that mark the boundary of his legal authority. Behind him stands an army forged in nearly a decade of brutal warfare. Ahead lies uncertainty, civil war, and the possibility of ruin.
Most men in his position would play for time — hesitating, negotiating, and seeking to mitigate their risks. But not Caesar. He gives the command to cross.
As his legions make their way through the cold, silent water, Caesar stoically remarks: alea iacta est — “the die is cast.” Only two options now lie before him: victory, or death.
Today, we explore what Caesar’s historic decision to cross the Rubicon reveals about the nature of risk taking, and the necessity of burning bridges. Keep reading to learn why, on the path to greatness, hesitation is the greatest risk of all — and why you can’t afford to look back…
But first — this summer we are hosting our first ever INVICTUS retreat, The History of Rome as Told by Its Heroes.
We’ll be sharing more details later this week, so keep an eye on your inbox. If you love the Eternal City and the Roman Empire, you do NOT want to miss this…
Caught In a Political Trap
For years, the Senate had watched Caesar with growing unease. His conquest of Gaul had made him the most powerful general in Rome. His troops were fiercely loyal, his coffers overflowed with the spoils of war, and his popularity among the people of Rome was unmatched. But success came with enemies.
His former ally Pompey turned against him, aligning himself with the Optimates, the Senate’s aristocratic faction. Before Caesar’s term as proconsul had officially expired, Pompey and the Optimates demanded he disband his army before returning to Rome. It was a trap, and Caesar knew it.
If he obeyed the Senate's command, he would be politically defenseless. His enemies would put him on trial, strip him of power, and send him into exile — or worse.
But Caesar wasn’t reckless. He sought compromise, proposing that he would relinquish command of his legions if Pompey did the same. The Senate, however, refused his requests. They weren’t interested in negotiation — they wanted him destroyed.
Crucially, Caesar understood that he had to make a decision, and quickly. That he would be declared a public enemy sooner or later was inevitable. But the terms on which he approached the inevitable were his to dictate.
If he hesitated, he would lose everything — his troops, left in uncertainty, might lose faith in his cause and disband. His political allies in Rome, sensing his hesitation, would abandon him.
Indecision would destroy Caesar just as surely as any other threat he faced. So he made up his mind — he would not back down without a fight…
The Die Is Cast
The Rubicon was a small river, unremarkable in most contexts. But as Caesar’s army approached, it became the dividing line between order and chaos, between peace and war.
Caesar understood that the moment he stepped beyond its banks, he would cease to be a Roman general acting within his legal command. He would become a traitor to the Republic, an enemy of the state.
While it might be true that “pessimists are either wrong or disappointed, but never both,” Caesar understood that pessimists do not win wars. He realized that a willingness to risk defeat — and all its repercussions — is a prerequisite to writing history.
And so he consulted with his officers, gauging their resolve. He conveyed to his men the gravity of the situation — once they crossed the river, there would be no retreat, no second-guessing. They would triumph, or they would die.
His men of one mind, Caesar gave the command, committing himself to his course of action.
He cast the die, and crossed the Rubicon.
No Turning Back
The Senate reacted swiftly, declaring Caesar an enemy of Rome. Pompey and his allies fled the city, raising legions to crush him. They believed that, sooner or later, Caesar would falter. They believed the enormity of what he had done — and the scale of the forces against him — would break his will.
They were nearly right. At the Battle of Dyrrhachium, Caesar suffered a costly defeat and was forced to retreat into Greece. But even now, he was able to work this setback to his favor.
Pompey, who had previously avoided confronting Caesar in pitched battle, preferred to wage a war of attrition against him. Yet following his victory at Dyrrhachium, Pompey’s officers began pressuring him to face his opponent head on.
Intuiting this, Caesar now took his biggest gamble yet. On the fields of Pharsalus, he deployed his troops in such a manner that gave Pompey almost every conceivable advantage — from battlefield positions to numerical superiority.
As Pompey took the bait, Caesar now relied on the only thing he had to his advantage — the experience and training of his men. During the battle, his troops employed techniques they had learned in Gaul to defeat Pompey’s cavalry, which was more than five times the size of their own.
Over the course of the brutal battle, Caesar’s men proved that strength, discipline, and sheer force of will can overcome numerical superiority. That, in addition to Caesar’s cunning tactics (perhaps to be covered in a later article), won them the day. Pompey’s forces were crushed.
Ultimately, Caesar triumphed in the civil war because he understood something his enemies did not: once your decision is made, there is no room for hesitation. There is no room for regret. You fight until you win.
Victory was not immediate. It was not easy. But by refusing to retreat, refusing to question himself, and refusing to stop until the war was truly won, Julius Caesar carved his name into history.
Takeaways
1) Make a Decision
The worst decision is indecision. While he was still in Gaul, Caesar’s enemies hoped he would hesitate and second-guess himself. But Caesar understood inaction would destroy him just as surely as failure. He moved with purpose, and made his decision.
2) Cross the Rubicon
Once you are resolved, commit yourself fully to your course of action. Don’t hedge your bets. Don’t leave yourself an escape route. Those who try to keep all doors open never walk through any of them. Cross the Rubicon, and don’t look back.
3) Lead Your Men to Victory
One the battle is joined, don’t stop fighting until you win. While the occasional tactical retreat is permitted, you must be willing to fight to the death for your cause. Caesar won because he never wavered. From the moment he crossed the Rubicon, he knew it was victory or death — he made his choice, and made history.
Want to dive deeper?
James and I go live on X this Thursday at 9am ET to discuss the life and career of Julius Caesar, from his birth up to his crossing of the Rubicon.
Visit Evan’s X account at 9am to access the livestream — once it ends, the stream will be added to our Members-Only Video Archive for you to catch the replay.
Also this Thursday, our premium subscribers will get a deep dive article on the creation of the First Triumvirate — the secret pact between Crassus, Caesar, and Pompey to control the Roman state.
If you’re not already a premium subscriber, please consider joining below — or upgrade to our exclusive Praetorian Guard tier of membership:
Ad finem fidelis,
-Evan
One more thing…
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