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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:

If you enjoyed this article, you'd be crazier than a young Caligula not to sign up for the newsletter. When you do, I'll send you a free copy of my travel notes from the latest bike tour along Via Appia.

After Benevento, nobody knew the way. Even in ancient times, Via Appia ran haphazardly through the southeast. The exact route depended on the outcome of battles, the terrain in question, and the politics of local cities and villages. Sometimes the way was too rocky and steep to build a permanent roadbed, and in other places the land was so flat that a permanent road didn't seem necessary.

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

In most of the historic towns of Italy, if you head uphill you’ll automatically get closer to the castle, the duomo, or whatever was the most important building a thousand years ago. Modern Italian cities grow outwards from their ancient core.

As I climbed through Benevento, the streets grew more narrow and the buildings began to look older. There were important sites here that I wanted to see, so I parked my bike outside a bookstore and went in to buy a book on the history of Benevento. One of the owners was a well-informed amateur archeologist.

“This bookstore,” he said, “was built over a pagan temple. It was the cult of Dionysus. We have one of the original pillars built into our wall, over here.”

There was a little alcove in the wall with a column of marble exposed inside. I had thought it was a replica sitting on a shelf, but I could see now that it extended down below the floor. They had put up the wall around it.

I love to stumble upon old reminders of the ancient world, and I could tell the bookstore owner was a kindred spirit. He showed me where he thought the entrance to the temple would have been, and where the altar would have been placed.

He tapped a spot on the wall and said, “Every year, on the spring equinox, the sun touches right here.”

Before I left he told me where to find the Roman amphitheater, the famous Arch of Trajan, and his favorite gelateria.

The stones of the amphitheater radiated warmth in the afternoon sun. There weren’t many people around. I jumped from step to step, and listened to my ocarina echo through the site. An archeologist showed me the place where the ancient Via Appia ran right past the stadium entrance.  

A warm drizzle of rain fell on me, but it stopped in a few minutes. The moisture added a sparkle to the bright orange tufa bricks and creamy travertine of the amphitheater.

This is what I had come here for. To follow the path of the ancient Appian way, as well as I could, to seek out and enjoy every possible trace of ancient Rome, to finish the journey yet be open to any experience that came up. I was fully enjoying this beautiful moment. 

I never get tired of ruins from the ancient Mediterranean. I'll bask in their sad, warm presence, every chance I get, until I die. 

I was reluctant to leave Benevento, but I had to make some plans.

Up to now, I had followed a clear path through territory that was mostly familiar. The original ancient Appian Way had been laid out well down to Benevento. I knew where to go, and I had visited much of the area before.

After Benevento, nobody knew the way. Even in ancient times, Via Appia ran haphazardly through the southeast. The exact route depended on the outcome of battles, the terrain in question, and the politics of local cities and villages. Sometimes the way was too rocky and steep to build a permanent roadbed, and in other places the land was so flat that a permanent road didn't seem necessary. 

We know the via Appia certainly went to a few specific towns, and there are others where it probably passed. But the “road” could have been just a gouge in the rocks, a swath of grass cut once a year, or a length of paving stones that farmers carried off later to grind their flour and olive oil. 

I would try my best to connect the dots between the few places which we know were part of Via Appia. But after Benevento I would have to find my own way. 

Or would I? 

I had another option, which I turned over in my mind as I rode towards another important Benevento monument, the Arch of Trajan.

Rome built this arch to glorify the benevolent, magnanimous side of the emperor Trajan. It shows him meeting peacefully with barbarian kings and giving bread to poor Italian children. There are symbols of the Roman Empire, along with symbols of victory and loyalty and the four seasons.

Trajan’s Arch also marks the point where the Via Traiana branched off from Via Appia. This was a shorter, more certain route that followed the Adriatic coast. The emperor Trajan built it to speed up travel to the ports at Brindisi, Bari, and Lecce.

I thought about taking the newer Via Traiana, and spent a long time staring at the Arch while I decided what to do.

There would be more traffic along Via Traiana, and fewer historic sites. But there would be more campgrounds, and I could probably get to Brindisi a few days earlier. That could turn out to mean more time with Gisela!

There was very little risk of getting lost on Via Traiana. But if I took Via Appia, I wasn’t sure where to go after Benevento.

It was the uncertainty that decided it for me. Which route would lead me through more oak forests, over steeper hills? Which way was I more likely to enjoy a conversation with strangers?

My goal was not to get to Brindisi as fast as possible. It was all about the journey. The Appian Way held more promise of discovery and adventure, and that’s what I wanted from this trip. 

I left Benevento heading southeast, my best guess on the route of Via Appia, roughly in the direction of Venosa. 

The ancient Roman poet Horace had written an account of his own journey, “Via Appia With Stops.” Venosa was Horace’s home town, and Via Appia definitely passed through here. The town of Venosa was on the other side of the Apennine mountains, but this was now the only direction I had.

 I rode into the evening, though I didn’t know the way. I didn't know where I would sleep that night, but something told me to just keep riding.

The road meandered back and forth through scrubby hills, then weaved through dense forest. The blinking light on my handlebars made a dim circle on the pavement in front of me. Besides that, I could only see the dark silhouettes of trees.

I was puffing hard now as I climbed ever-steeper slopes. There weren’t many cars, but when they passed, the  headlights cast gorgeous shadows from the branches and leaves. I rode past small villas and buildings that looked deserted.

Then I reached an especially steep hill. The road seemed to dive bomb into a dark forest, winding down and farther down. I could only see a few feet ahead of me, and I wondered if I was destined to go over the edge of a cliff. I could feel the temperature rise. 

Finally the ground leveled out, the sky cleared, and stars winked at me overhead.

It was a warm night, and I felt like I was coming home, like I had been there before. Everything seemed oddly familiar, though I didn’t know where I was or where I was going. It felt good to just keep riding through the night. 

Finally, I found a wide, rutted dirt road leading uphill away from a turnout. It looked like it hadn't been used for a while. I walked my bike along this track, which soon became more like a field. There were pine trees on my left and olives on my right. Up at the top of the hill, I saw the silhouette of a house.

There were no lights on, but I was going to try to ask permission before I camped. I left my bike and walked up the lumpy field that had started out as a road. Soon I was trudging through soft earth, walking between young olive trees and grape vines. The “house” turned out to be a row of tall sheds. Nobody was around.

I gave up, and walked back down to my bike. But after a few seconds I stopped cold as I saw a small, pale light in the distance. I called out a friendly greeting. There was no answer, but what I saw was unmistakable.

Someone was down there in the trees, waiting quietly between me and my bicycle.

This is the 14th 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:

If you enjoyed this article, you'd be crazier than a young Caligula not to sign up for the newsletter. When you do, I'll send you a free copy of my travel notes from the latest bike tour along Via Appia.

A few thousand years ago, something happened at a place in southern Italy called Maleventum. 

Roman soldiers facing a charge of elephants at Beneventum--Public Domain
Pyrrhus' elephants. Public Domain

Maleventum means a bad wind or a bad event. At Maleventum, the Roman republic had its final confrontation with Pyrrhus. 

Pyrrhus was a conqueror who wanted to turn the Italian peninsula into his own private dictatorship. He beat the Romans in several battles.

Pyrrhus was the only thing that kept Rome from realizing her vision for a true republic.

The Romans never defeated Pyrrhus, but at Maleventum they put up enough resistance to convince him that conquering Italy wasn’t worth the cost. He packed up and left for greener pastures.

This is the origin of the term “Pyrrhic Victory,” and Maleventum was renamed to Beneventum, or “good event.”

Your own personal Pyrrhus

You have a personal Pyrrhus that is holding you back. Pyrrhus is the obstacle that is keeping you from your destiny. 

Your Pyrrhus could be your self-talk. Your fears and insecurities. It might be a real, tangible disadvantage. 

Your Pyrrhus could be something you were born with, or something that happened to you. Your Pyrrhus probably seems like something you can never overcome--and that’s the key.

You can fulfil your destiny as soon as you realize you don’t actually have to defeat Pyrrhus.

How to rise above any obstacle

In 279 BCE, Pyrrhus sent envoys to Rome, demanding they surrender. 

Appius Claudius delivered Rome’s answer, and it’s one of the most memorable things he did. In a public speech that promised Rome would never give up, Appius Claudius said, “Every man is the architect of his own fate.”

Romans were inspired to rise up, to be the best that they could be. So they kept on fighting Pyrrhus, but they also kept on building roads and aqueducts, growing crops, trading and farming and legislating. 

They became so good at being Romans that Pyrrhus eventually didn’t matter. The battles he won didn’t have any significant impact on the lives of most Roman citizens. So Pyrrhus left, undefeated but ineffective.

You, too, can rise above an unbeatable obstacle. Do the best you can, be the best you can, wherever and whenever you can. Your problems won’t go away, but they will become far less important. 

You obstacle might be a huge stone that refuses to budge. But you can become a surging river, flowing right over and around the immovable stone. Does the river even notice the stone?

Your Pyrrhus doesn’t matter. It has no power over you.

When you discover you are no longer held back by Pyrrhus, you are having your Benevento Moment. You have endured and prevailed. You have found your fire.

My Benevento Moment

Arch of Trajan Italy bike tour

Benevento is the crossroads where I had to make a choice and a commitment.

One of the most famous monuments in Benevento is Trajan’s Arch. It commemorates Trajan’s victories and accomplishments, but it also marks the beginning of a new road that branches off from the Appian Way.

This new road is the via Traiana (Trajan’s Way), and it follows the Adriatic coast to Benevento. This is a flatter, shorter, and easier route. The way is better known and more clearly marked. There are more places to find food and lodging, and you’re never far from a beach!

I was tempted to take via Traiana the rest of the way. It would mean a safer, easier, possibly shorter route. 

I’m a timid traveler. I usually favor comfort and security over the unknown. But my goal for this journey was practically the opposite. Did I want to shorten my trip, get back to Rome a few days early, just to wander around old paths I’d been down many times before, trying to relive my youth and my past?

It only took a few minutes to move beyond the temptation. I continued on the most uncertain and remote part of the Appian Way, into the Apennine Mountains. This choice led to some of the most memorable parts of my journey.

A decision awaits you at your Benevento moment. What choices will you have to make? You may be tempted by an easier, safer path. Will it bring you what you want?


Once you get outside Benevento you hit some beautiful country right away. There was no way I could have predicted the amazing show that was waiting, but that's the serendipity of bike tours.

It was going to be a major turning point in the tour, and after this night I would spend a lot more time talking to people, sharing stories and experiences, being social. But as I left Benevento, I didn't know yet what was about to happen.

I rode my bike out of the city early in the evening. A traffic cop told me the way, and soon I was cruising along a winding, hilly country road in the failing light.

I didn't have plans for where to stay that night, but here's the great thing about touring southern Italy by bicycle. Your tent almost anywhere in the countryside.

In fact, when I met an old man walking along the side of the road and asked if he knew anywhere to camp, he smiled and gestured magnanimously across the forests and meadows around us.

"You are welcome to camp anywhere you want in my country," he said.

This was just my second night of stealth camping on the tour of via Appia, but I've always had great luck when I leave things up to chance.

The land was deep green, with beautiful oak forests and grassy meadows. At one point I passed a sign leading to the Ponte Rotto, where I would one day fulfill my dream of camping out in ancient Roman ruins. But not this night.

I rode my bike down into a broad valley as the last glow of the sunset disappeared. The world was pitch black. The only light came from my flickering Cat's Eye bike light and the silver points of stars up above.

I came to a farm at the top of a gentle hill covered with olive trees and grapevines. Nobody seemed to be home when I went to ask permission, so I found a level spot near a bunch of olive trees and set up my tent.

I was ready to crash when I saw a dim light gently bobbing near the spot where I had wheeled my bicycle off the road. It looked like someone walking with their cell phone, so I shouted a friendly "Buona sera!"

No answer, but the light kept coming closer, taking its time.

I didn't want to startle anyone in the dark, so I turned on my flashlight, pointed it at my own face, and called out another greeting down the hill.

No reply, and this began to feel creepy.

"Listen," I said in my best possible Italian, "I'm just passing through here on my bike and I stopped because it is dangerous to ride in the dark. I wanted to camp here for the night and leave early in the morning, but I don't want to cause any problems. I'll go now if you want me to."

The mysterious light stopped, but continued to bob gently in the air, flickering on and off. I pointed my light at it, and saw nothing but the low branches of a young oak tree.

A ghost? This wasn't the only time I've ran into ghosts in Italy (that's another story) but something felt completely normal and natural about this. I walked down to the light and found a large insect on a tree branch. Its abdomen was glowing, and the branch bobbed up and down in the wind.

I laughed out loud as I walked back to my tent, and suddenly a flash of light in the sky caught my eye. A shooting star! A few minutes later I saw another one. The next hour or so was a treat of meteors, stars, and glowing insects.

What happened next is hard to describe, but I'll try. Laying there in an olive grove in Italy, I felt like I was coming home. I had found a part of myself, something I had lost over the years.

Italy is famous for her natural and artistic beauty, but I've been guilty of neglecting the first of these. When I tour in Italy I tend to obsess on paintings and history, cold sculptures and crumbling chunks of marble. But those things get there romance and their magic from the natural world that shaped them and the people who made them.

The whole point of a bike tour in Italy is to breathe life and relevance into the textbook Italy we all think we know.

It took a natural light show in the olive groves of Benevento to show me the error of my ways.

Come to think of it, this is one of the most important reasons to go on a bike tour. It will get you out of your routing, your regular mindset, and show you what you've been missing out on.

I don't spend as much time in cars as most people do, but even so I'm fixed in my ways, just like we all are.

And there's nothing like a bike tour to take you out of yourself and show you the world in a new way.