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No matter what adversity you’re facing, no matter what metaphorical Pyrrhus is invading your life, keep on striving to be the best possible version of yourself. Eventually you’ll become so good that you’ll make your biggest worries irrelevant.

(If you're new to this story, here's the link to Chapter One:

In 282 B.C.E, the Romans had a bad relationship with the Greeks in southern Italy. When Roman warships approached a harbor near Tarentum, it was the last straw. The Greeks invited a king named Pyrrhus to fight for them against Rome.

Pyrrhus loved war. He spent much of his career invading other lands and getting rich off the spoils. Pyrrhus also had a knack for marrying wealth. He had 5 wives during the course of his life, mostly princesses or queens who helped to fill his coffers and finance his wars.

Pyrrhus may have had a sincere desire to help his fellow Greeks. But he also recognized a tremendous opportunity. If he could conquer Rome, he could become the king of the whole Italian peninsula.

Pyrrhus arrived in Italy with a mighty army. Three thousand cavalry. Two thousand archers, plus another 500 warriors armed with slings. Some twenty thousand foot soldiers. Altogether, more than 25,000 highly-trained Greek warriors.

There were hoplites, tough men reared in the hard country life on the rocky slopes of Greece. The best of them could split a tree trunk with a javelin from 100 feet.

There were the Epirotes, fierce and loyal subjects that Pyrrhus hand-picked as his elite personal guard.

But the pride and might of his army consisted of 20 elephants trained for war. Their tusks could sweep away soldiers like blades of grass. Their feet could crush the survivors. The archers on their backs would rain death upon their foes.

Over the course of a few years, Pyrrhus drove back all the Roman armies that came up against him. The other parties in Italy left him alone, or actively helped him. Pyrrhus was already planning how to run his new kingdom, and even expand it into Sicily. Total victory seemed inevitable.

 But he was about to be stopped by a grumpy old man.

In 279 BCE, Pyrrhus sent envoys to Rome, demanding her surrender and offering generous terms. If the Romans had accepted Pyrrhus’s offer, southern Italy might have remained Greek to this day. The Roman Empire as we know it would never have existed. There would have been repercussions for Christianity, Judaism, Islam, and ultimately the conquest of America.

For better or worse, you would be living in a different world today.

The Roman leaders could have accepted, and it would have avoided bloodshed in the short term. Has life ever offered you a tempting bargain like this? 

Give up some of your freedom, stifle a little bit of your creativity, compromise your vision and your dreams. In return, things will be comfortable for you, and you can avoid confronting the scary obstacle that’s in your way.

There’s no shame in accepting such an offer. Many people have done it. I’ve done it. But the world becomes a little bit sad every time it happens.

You probably think of Rome as a decadent empire. They invaded three continents and subjugated the inhabitants. They destroyed cultures and enslaved populations. There’s a reason that Rome has been the villain in many stories around the world.

Still, I’m begging you to take the Roman’s side in the story of Pyrhus. Most people had at least some rights and freedoms in the early Roman Republic. You could improve the quality of your life through merit. Even if you were a woman or a slave, and life was brutally unfair, you had some legal protections and the chance to make things better for your children, if not for yourself. 

The Roman Republic wasn’t perfect, but it was better than the dictatorship that Pyrrhus wanted to impose.

This is why Appius Claudius was able to sway the people, and even inspire them. When he said, “Every man is the architect of his fate,” he was telling Pyrrhus’s envoys that Rome intended to remain the architect of hers. This was also his way of reminding the Romans that they were responsible for their own destiny. 

The Romans utterly rejected Pyrrhus’s call for surrender, and a war began.

Things went well for Pyrrhus in the beginning. He defeated one Roman army after another. But there was a cost. He couldn't easily replace his fallen soldiers. In contrast, the Romans could draw upon a large supply of loyal warriors.

After an expensive victory in the battle of Asculum in 279 BCE, Pyrrhus said, “If we defeat the Romans one more time, it will destroy me.” This is said to be the origin of the term, a Pyrrhic victory.

At last, the Romans were becoming the architects of their own fate. Even while they were losing battles against Pyrrhus, they kept on building aqueducts, writing philosophy, growing crops and establishing trade. 

That’s how you overcome your biggest obstacle. You do the best you can with what you have. 

No matter what adversity you’re facing, no matter what metaphorical Pyrrhus is invading your life, keep on striving to be the best possible version of yourself. Eventually you’ll become so good that you’ll make your biggest worries irrelevant. 

That’s when the universe usually throws you a chance to finally overcome an obstacle. This has happened to me twice. Maybe it’s happened to you. I call it a Beneventum Moment, and pretty soon you’ll know why. 

Pyrrhus pounded his way north like an unstoppable juggernaut. If he could keep going long enough to overpower the city of Rome itself, the war would be won. 

If his strength failed before taking Rome, it would be the end not only for Pyrrhus in Italy, but for all the Greeks in Italy and for the Samnites, too. The outcome would determine the future of the Italian peninsula, the history of Europe, and the destiny of people all over much of the world.

The final battle took place somewhere south of Maleventum, the place of the evil wind.

Now, let’s remember that somewhere south of Maleventum, in a dark grove of olive trees, I was looking at a strange, pale light on the path between me and my bicycle. 

“Ciao,” I called out. There was no reply.

 “Buona sera,” I tried again.

Still no answer, but the light bobbed gently up and down. It looked like someone was walking with their phone held out.

“My name is Jacob,” I continued in Italian. “I'm touring Italy on a bicycle and I want to ask your permission to stay here in my tent for one night. Is that ok?”

The light stopped moving, but still nobody replied.

I had a flashlight in my pocket. I turned it on and pointed it at my own face. “You can see me now,” I said in Italian. “I don't want to cause any problems. I'll leave if you want.”

There was no reply, but the mysterious apparition stood its ground.

I waited for half a minute for a voice, for the light to move, for anything to happen. The poor man or woman must have been terrified of me, rooted to the spot. That’s what I told myself, but the truth is, I was feeling scared.

“Do you speak English?” I asked. “Parlez-vous francais?” 

I repeated my greetings and introductions in every language I could remember. This went on until I exhausted my linguistic acumen a few seconds later. All I got was a disturbing silence. The strange light quivered in the distance.

All I wanted now was to leave. I just wanted to get on my bicycle and ride away. I didn't like being lost in a dark forest, with a frightening apparition right there on the path between me and my bicycle.

Finally I said, “OK, I'm going to walk towards you. I just want to pick up my bike. I'll take my bike and go away. I'm sorry if I disturbed you.” I pointed my light towards the ground, and waited a minute for my eyes to adjust to the dark again.

I walked slowly down the hill, and I kept the hovering pale light in my sight. It looked like I would have to walk past this person to reach my bike. 

As I got closer to the light, I thought that maybe the person standing between me and my bike was just distracting me while his accomplices waited in ambush along the sides of the path. Murder or abduction, velociraptor style.

My heart beat faster. I tried to remember everything I had ever heard people say about self-defense. In a few seconds I worked out a plan.

When I got close to the person who stood there, I would suddenly raise my flashlight and shine it right in his eyes to blind him for a few seconds. Maybe bash him in the nose with it, so his eyes would water. Then I would run for my bike and get the hell out of there. 

The light was now about five feet away. With a shout, I leaped across this last distance and aimed my flashlight where I thought his head would be.

I tripped over a rock or a stick, jarred my knee and dropped my light. I rolled on the ground, then got back up and limped for the bike. It was laying on the ground where I had left it. I groped clumsily for the handlebars. The weight of the panniers made it hard to raise, and one of the pedals banged my shin.

During these perfectly-executed maneuvers, I was certain somebody would run out of the pine trees and grab me. But they didn’t. I only heard a faint wind. The sound of crickets. A small rodent lurking among the olive trees.

I saw my flashlight light laying on the ground, the beam shining on the grass and shrubs. A small bush waved its branches in the breeze.

As I finally picked up my bike, the mysterious light re-appeared, bobbing gently up and down.

“Okay,” I said. “I guess you’re not going to hurt me. I’m just going to pick up my flashlight and leave now.”

I set down my bike again, and inched my way to the light on the ground. Then I couldn’t resist the temptation. I pointed my beam straight at the glowing bit of light, and I yelled, “Show yourself!” 

I might have done this a little too dramatically.

All I could see was a young tree. I walked closer, and saw a thick caterpillar on the tip of a branch. White bands ran along its back. I took away the light, and the white bands glowed in the dark. 

All this time, I had been talking to a glow-worm on a branch. 

Somewhere south of Maleventum, the Romans made camp and prepared for a final stand. They knew it was only a matter of time before the Greeks and Samnites attacked.

The fight began at night, and lasted most of the next day. Neither side could seem to get the upper hand.

Then, a Roman soldier noticed that the elephants were steering clear of the watchfires. He and his companions grabbed flaming branches and threw them towards an elephant, who reared up and ran back. 

This turned the tide. The Romans drove the elephants back with burning sticks, hot coals, anything they could set on fire. They wrapped their arrows in oil-soaked rags and turned them into flaming missiles. The huge animals ran back and trampled their own masters.

Even after this new development, Pyrrhus still drove the Romans out of their encampment. But it was an expensive victory. The Battle of Maleventum depleted his army and killed more than half his elephants. He packed up and sailed back to Greece.

From the Roman perspective, this battle was a change in the wind. To recognize the fact, they renamed the city of Maleventum to Beneventum, which means “good wind.” 

The city of Benevento was born, and Rome had her Beneventum Moment.

Somewhere south of Beneventum, I laughed out loud as I set up my tent. So many dangers and worries turn out to be nothing. Pyrrhus turned out to be a footnote in Roman history. My biggest fear turned out to be a cute little bug. Whatever troubled me for the rest of this journey, I would just shrug it off.

By the time I was ready for bed, the trees were flashing with lightning bugs. Overhead, a million stars twinkled in answer. Far away on the horizon, bolts of lightning added to the brilliant light show. Before I went to sleep, I saw a meteor scrape a bright line across the sky.

This dark, mysterious place was full of light, rich with omens. As I fell asleep in my tent, the ghosts of cavalry, of bandits, of poets and pilgrims marched through time only a dozen meters away.

This is the 15th Chapter of my book, Rome to Brindisi: How Biking Down an Ancient Roman Road Saved Me From a Life of Quiet Desperation. I'll be posting a few chapters each week during the Covid19 shutdown. I'm also reading them out loud on YouTube (check the menu for links) so you can listen while you're shut in. Here's the next chapter:

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