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The sun was setting, and I had nowhere to sleep. Prostitutes and their customers would soon be lurking about, and there were even worse things knocking around in my own head. 

I had food and water and a tent. I was surrounded by empty fields, bushes, and many opportunities for a good night’s rest.

But I pictured the carabinieri picking me up as a vagrant. Desperate refugees holding me for ransom. Worst of all, I imagined the Italians would think I was a pestilent, mouse-raping transient. When they saw me sleeping out in the open, the people of Lazio would surely turn away in disgust and say, “Che schifo!”  

Why hadn’t I planned better? Why did I waste so much time throughout the day?

After you leave the park of Via Appia Antica, you can follow the original ancient route of Via Appia just by sticking to the national highway SS7. But on the periphery of Rome, this road is full of traffic. 

In the 18th century they built a parallel version of Via Appia nearby, called the New Appian Way or Via Appia Nuova. It runs in the same direction, but you pass through a sterile urban landscape. This route is useful for commuters, but there’s nothing to see except endless apartment blocks and one short glimpse of some crumbling aqueducts. 

I stayed on SS7. Eventually the houses and shops gave way to more open country. I followed the road through suburbs, farmland, and acres of grape vines. 

A few miles farther down, a small sign said, “Via Appia Antica.” An arrow pointed off the road towards a gulch.

I followed this path to a stretch of the familiar basalt stones that the Romans used. For the next few miles I rattled past fields of tomatoes and artichokes. Grape leaves waved at me from thick vines as I rode by. Best of all, there were fallen pillars and the occasional remains of a wall.

Later in the day, after the old stretch of Via Appia went back to the main road, I passed through a pungent cloud of sulfur and saw an old man filling plastic jugs from a small fountain. 

“E' potabile?” I asked. Is the water drinkable?

“Si!” he said. “It's good for the bones.” He gestured for me to try it.

The smell was like a decomposing pile of manure from a cow with chronic diarrhea. Millions of tiny bubbles clouded the water. 

It’s worth noting here that Italy boils with volcanic activity. Vesuvius and Etna are the most famous Italian volcanoes, but there are many others. The Alban Hills just south of Rome erupted some 30-40 thousand years ago, creating the basalt that eventually paved Via Appia.

Geologists think an eruption will happen again. Occasionally a few sheep are killed by toxic gas, which is proof that something is still going on down there. 

There are many springs in Italy that provide water rich in dissolved minerals and gases from this geothermal activity. Apparently I had just stumbled upon one of them.

I thought about the sheep poisoned by gas from the volcanic earth. But when in Rome, do as the Romans do. I drank the old man’s clouded water. I’m not aware that anything bad ever came of it, but I probably need to put in a disclaimer here:

So… I hope you understand that I am not a doctor. This story is not intended as a recommendation to prevent, treat, or cure any disease. You should always consult a medical professional before you drink murky, foul-smelling water while traveling in a foreign country.

Some time after drinking from the volcano, I rode into Ariccia, an important place long before the Romans came to power. Every major art museum in the western world has Romantic paintings that show gods and nymphs in a wooded setting. Many of these scenes were inspired by the forests of Ariccia. 

Ariccia was also the first staging point along Via Appia. Messengers and important officials picked up fresh horses here. Travelers would stop in Ariccia to pick up supplies or stay for the night. 

I bought food at a small market, including a cylinder of goat cheese with a bitter smell. The shop owner insisted it would not spoil for many days, and he was right. When I combined the cheese with bread, olives, tomatoes, and a bottle of cheap-but-effective aglianico wine, I had a banquet. 

I should have either stayed in Ariccia for the night, or avoided the town completely. It took a while to get back on SS7, and there wasn’t much time left to ride. As the sun dropped low in the sky, I started to wonder where I was going to sleep.

I had my tent, and I had always thought I would just plunk down and camp wherever I found myself. But my own mind was determined to make things difficult.

When I was in college, I spent a few years living in the redwood forest above the UC Santa Cruz campus. This was a tradition at the time, and there were many “woods dwellers” living among the trees.  

I loved waking up to the sound of birds. I loved that I didn’t have to pay rent. I loved feeling like I wasn’t an ordinary muggle. When other students went back to their dorm rooms, complaining about the cold weather, I would hike into a dark forest to go to bed. I was proud to live a secret life.

But this pride was always mixed with private shame about being homeless. I had a job, clean clothes, and a shower almost every day, but I didn’t have an address. I was missing one of the cultural trappings that qualify you as a normal person. 

Over years of travel I’ve slept in cars, in boxcars, under bridges, and in trees. I’ve slept in the snow, in the rain, on concrete, on broken glass, on closed roads and in open pits. I’ve slept in backyards, freight yards, and even once in a graveyard. I can feel safe and comfortable almost anywhere. But I never escape the self-conscious shame of looking like a bum.

The shame felt a hundred times worse in Italy. I was a guest in this country.

However, I had to sleep somewhere, and there’s always one foolproof way to defeat the doubts in your mind: Don’t give yourself a choice. 

After the sun went down, I didn’t have many options. This made it easier to find a break in the bushes, wheel my bike off the road, and pitch my tent in a field. The rows of vegetables had been cut. Whatever crops the farmer cultivated were already harvested. I wouldn’t bother anyone here. Nobody would even see me.

As I set up my tent, my courage grew. I thought about Seneca, the Stoic philosopher who wrote a Guide to Happiness. Seneca was rich and important, but when traveling, in his own words, “I put my mattress upon the ground, and lay upon it.”

If stealth camping was good enough for Seneca two thousand years ago, then who was I to worry about it? 

I had olives and goat cheese and fresh bread in my panniers. I feasted in the field, watching the very last glow of daylight fade away. I made a truce with myself, and felt my confidence return. 

Today I drank from a volcano. I could go anywhere and do anything. Where to sleep was just a petty detail. This bike tour was my mattress, and I would lay on it. 

But before I went to sleep in my tent, my phone lit up with a text from Gisela: “Good night. TVB.” 

The last three letters stand for “Ti voglio bene,” an Italian way of expressing sincere affection. I knew that my inner peace wouldn’t last. Demons gathered, ready to haunt this reckless traveler soon enough.

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It’s all wrong, but I’m doing it anyway. 

I’m on a plane, zooming to Italy, and I should be happy and excited, but I want to curl up into a ball and cry. The only way I can really pull this off is by breaking some rules and running up a huge credit card debt. Totally selfish, irresponsible, self-indulgent. 

As I write this I want to scream at you: This bike tour is the dumbest thing I ever did! Learn from my example. Do not try this at home. 

Worse still, do not try this somewhere far away on another continent where the language and cultural barriers mask all your personal flaws, disguising your deepest self-doubts underneath a glowing cascade of perfect Instagram photos.

I want to scream this at you, but there’s a stronger voice, one that says you’re here in this world to drink life to the dregs and have a wealth of vivid experiences. That both you and the world you live in were made by something more profound than you can ever fathom, and that you should show your appreciation by greedily savoring every facet and feature of this unlikely gem. 

We’ll get back to this, but first you should know a little bit about where we are.

As you leave the center of Rome, just southeast of the Colosseum, you can ride your bike on a long stretch of the original via Appia that has been lovingly restored. If you come in the spring, you’ll see tall, waving fields of grass with billions of bright flowers.

Best of all, this place is the winning lottery ticket for ancient history nerds. You get to ride over cobblestones with ruts and channels carved by thousands of wagon wheels over the years. You’ll see crumbling structures of ancient brick, chunks of marble and sometimes a carving or inscription that gives a clue about the history here. 

Virtually all the monuments in the first few miles outside the city were the tombs of wealthy Romans. A burial along via Appia was an essential status symbol. During the height of the Roman Empire, you could barely see the green fields all around you. Tombs crowded the sides of the road, rammed together like passengers in the subway of some ancient ghostly rush hour. But there are even more dead buried underground. 

Centuries ago, Romans built catacombs along the via Appia. There are a few Jewish catacombs, and some are dedicated to pre-Christian religions. But the majority of the catacombs, especially along the Appian Way, were built by the Christians of ancient Rome.

These catacombs were long tunnels lined with small niches to hold the remains of the dead. Some of these tunnels went on for miles through the earth. When it wasn’t convenient to lengthen a tunnel, the builders would dig another tunnel deeper down. Most of the catacombs contain three or more of these levels. And there are more than 40 of these catacombs scattered around the outskirts of Rome.

Thousands of dead bodies underneath your feet, monuments to a hundred more on the grass on either side of you. Yet this ancient cemetery is a park! 

Above ground, practically all you’ll see are joggers and hikers, spandex and dogs and all the other signs of the living. Kids kick soccer balls while their parents prepare a picnic lunch. Every weekend is like a big happy birthday party in a graveyard.

Still, you’re never allowed to forget the dead. There is one big tomb where hikers and bikers and joggers nearly always stop to gawk. 

As you come up the crest of a small hill, this sight will probably stop you, too: The tomb of Caecilia Metella. It stands out like a great tower above the flat fields all around, taller and bigger and better preserved than anything else on the Appian Way. 

The original tomb was a huge, round drum. Now it’s crowned with a circle of battlements biting the sky. In later centuries, different owners added small buildings around it, but these feel like an afterthought. The whole thing is the color of bleached bones, and that’s what it was built for. 

Marcus Crassus was the wealthiest man in the history of Rome. A woman named Caecilia Metella married one of his sons, and when she died her family built the most audacious tomb on this side of the Mediterranean.

This was where I stopped walking, seven years earlier, when I decided to bike the entire distance of the Appian Way. It’s a good place to tell you what this trip was really about. 

The truth is, I was running away. 

I was almost 40 years old when I made this trip. I was secretly terrified of reaching that landmark age (or beyond) with no employable skills or experience, still single, and clueless about what to do with myself. 

Whenever I’m feeling stuck, I find an adventure and I go after it. It’s my way of confronting the failures and mediocrity in my life. I stare them down and say “Things are going to change NOW.” 

I told myself this journey was a way to throw down the gauntlet and go through a dark place in search of the light on the other side.

But it was really just a self-indulgent escape. An escape from responsibilities and relationships. An escape from fear.

What if I was not powerful beyond belief? What if I was just an over-achieving dreamer, drifting into middle age with nothing to show for it? If I became that person at 40, what would my life look like at 60?

This is the kind of trip that might make sense if you found out you had a terminal illness. Or if you lost someone you loved, someone who urged you to enjoy life and dare to live it to the fullest. 

I didn’t have a tragedy like that to add drama to the story, but who says you need to wait for something terrible to happen before you do what you want? I say go out and fulfil your bucket list while your bucket is still full. 

Even if you have another 20, 40, or even 60 good years ahead of you, that’s less than a single brick in the long, ancient road of time.

I didn’t know if I was doing the right thing, but I was following an obsession that had haunted me for seven years. Foolish or not, I was going to ride while I still had some time left.

I would be lying if I said I didn’t have doubts about whether I was doing the right thing.

This is the 2nd 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 the out loud on YouTube (check the menu for links) so you can listen while you're shut in.

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.

All I wanted was to leave. I just wanted to get on my bicycle and ride away on a journey down Via Appia to the Achilles tendon of Italy. 

But there in the dark forest where I found myself, a frightening apparition stood on the path right between me and my bicycle.

This isn’t some kind of metaphor. I was literally in a grove of trees somewhere outside Benevento on a warm spring night. I needed a place to sleep, and had just discovered that perhaps this wasn’t the best place to do so.

Unfortunately, it looked like I might not be allowed to leave.

I’m jumping ahead, though. This story began long before I set off on a bike tour. It started literally thousands of years before I was born.

Once upon a time, an energetic band of free-spirited farmers and artisans built a young republic in a sunny Mediterranean paradise. 

But they were all doomed.

A ruthless dictator from the East had his eye on the treasures and spoils of ancient Italy. He was steamrolling up the Italian peninsula with thirty thousand warriors, horses trained for war, and a score of thundering elephants. He won battles. He took villages. One by one, the tribes and colonies surrendered to him.

And then, when everything seemed hopeless, one man stood up and blocked the conqueror.

He wasn’t a hero, a warrior, or a great leader. He was just a grumpy old man with bad eyesight and selfish ambitions of his own. But he gave a moving speech which ensured that Rome would never surrender. His name was Appius Claudius, and he proved that a speech can stop an army. 

Most of the time, old Appius Claudius Caecus was an arrogant, self-serving prick. Like the driver who cuts you off in the middle of an intersection. Or the person who lets their dog run loose and defecate in front of your house, and refuses to clean it up. 

But even you have your bad days, when you laugh at something inappropriate or forget to put the toilet seat down. Likewise, the worst of us are capable of doing great things. 

Appius Claudius had questionable ethics, but he made a speech that galvanized young Rome against her enemies, and he said one thing in this speech that has lasted for millennia: 

“Every man is the architect of his own fate.”

This story is mostly about my attempt to be the architect of my own fate. But I’ll also tell you a lot about the conqueror, the elephants, and especially Appius Claudius.

The speech was one of his last public acts, but he is better known for what he did at the beginning of his career. When Appius became Censor, he nearly bankrupted the treasury. He devoted almost all the available funds to build a road that was unlike anything anyone had ever seen before, and it led directly into the uncertain wilderness of the south. 

Then, as the keystone of a career that was built almost entirely on sheer chutzpah, he named the road after himself: Via Appia.

Why am I telling you this?

Because two thousand, three hundred and seventeen years later, I was riding a bicycle on that very same road, while every motor vehicle in Italy tried to crush me like a grape in a winepress.

Just after Via Appia leaves Rome through the Porta San Sebastiano, the shoulder disappears. Two brick walls guard the road, turning it into a roofless tunnel. It is a Roman Channel of Death for cyclists, where you are nothing but a petty obstacle, a dog turd to be avoided if possible or else smeared across the cobblestones.

Commuters in Fiats, late to work, shouted vulgar curses against my ancestors. Produce trucks threatened to grind me against the walls, an olive between the millstones. Tour buses nearly pounded me like basil in a mortar.

Soon I would be mashed into pesto, olive oil, and marinara sauce. The tricolore of Italy. This adventure would end before it began, and a foreigner would become national cuisine.

But somehow I made it to the Parco Regionale dell'Appia Antica. At a small building that provided tourist information, I asked if it would be possible to speak to an archeologist.

A receptionist set down her lipstick-stained cigarette and directed me to Dr. Grillo. His office was up the stairs, first door on the right. The door was open, and a grey-haired man, impeccably dressed, stared at me over a tiny cup of espresso. He seemed uncomfortable that a sweaty American, dressed in shorts and clutching a bicycle helmet, would enter his office this early on a weekday.

In the best Italian I could muster, I told him I wanted to bike the Via Appia Antica from Rome to its end in Brindisi. From the surprised confusion in his face, you would think I had just asked him to circumcise me.

"Impossibile!" he protested, pronouncing the word with long Italian vowels: eem-poh-SEEEEEE-bee-lay!

Nobody knows how many millions of nobles, senators, philosophers, soldiers, merchants, prisoners, slaves, poets and bandits have traveled on the Appian Way. They've been doing it for more than 2,300 years on foot, in litters, by wagon, buggy, horse, pony, donkey, elephant, mule, and more recently in cars, motorcycles and trucks. Surely one enthusiastic bicyclist could make the journey. 

I had already decided to take this trip, with or without anyone's help. But I wanted some advice and encouragement from an expert, if I could get it.

I wanted to see marble columns rising out of misty fields in the dawn. I wanted to remember what the Romans forgot when they became too powerful as an empire and too weak as individuals.

Dr. Grillo assured me that it could not be done. He warned me of floods and swamps and mountains. Much of Via Appia was buried on private property.  Also, there are many places where we simply don't know which way Via Appia went.

But I knew I had him when he asked why I would ever want to do such a thing.

This is the hardest question to answer, even in English. I did my best to explain my fascination with ancient Mediterranean history.

Archeologists will never finish scraping the ancient world out of the soil and gluing it back together. There's still an energy you can feel when you're alone in these ancient places.

Grillo understood. Or at least he no longer looked like he was planning to call security or throw me out himself.

When you travel by bicycle, I tried to tell him, you don't just "see" things behind the glass of a museum display or a windshield. You feel the air and the moisture and the contours of the land. You talk to the people and you’re exposed to the weather. You get the feeling of the place.

This is why, after staring down a 2,300-year-old highway, I found I could no longer try to run a business or be a teacher or fulfill any of the other roles the world put before me until I rode my bike to the end of the road, just to see what would happen.

Many Italians are gifted with a powerful intuition. Even if you don't know the right words, if you speak with passion they will read your mind and give you exactly what you want. Before I could finish, my new archeologist savior was nodding vigorously as he opened the squeaky drawers of his file cabinet, pulling out maps, old photos, and drawings.

He gave me a stream of directions and names and numbers in rapid Italian. I scribbled as much as I could understand in my notebook. I wasn't looking for perfection, I told him, just adventure and learning and new experiences. If I couldn't retrace all of the Appian Way, I would still cover the distance and do the best I could.

Dr. Grillo assured me once again that I was attempting something impossible. But he still shook my hand and said, “In bocca al'lupo.” In the mouth of the wolf, a Roman way of saying “good luck.”

Traditionally when someone says this, you're supposed to answer, “Crepi lupo,” which implies that if a wolf tries to eat you it will find you to be poisonous. You will kill the thing that tries to kill you.

However, an Italian friend explained to me that a mother wolf, like the legendary wolf who raised Romulus and Remus, carries her young by holding them in her mouth. If you are “in boca al’lupo,” you are protected by the mother wolf. You certainly wouldn't want the wolf to die.

Either way, I was about to set off into the unknown, on the back of a bike, in the mouth of a wolf.

Dr. Grillo wasn't the only person who said it couldn’t be done. Others predicted I would be robbed, kidnapped, bitten by snakes, infected with malaria and maybe trampled by water buffalos before I reached Terracina. One well-meaning blog reader sent an email to warn me, “The cobblestones will destroy your arse in the first 10 kilometers.”

Everything they told me was true. Via Appia is fraught with peril. It’s a 450-mile gauntlet of knee-grinding climbs, bone-cracking potholes, sheer drops in the fog, bad weather, hostile natives, robbers, murderers and things far worse than that. When you venture along the jugular vein of ancient Rome you’re going to encounter the best and the worst of Italy.

But there’s a reward for trips like this, something you know intuitively before you begin. A journey like this is going to change you. It must. There are too many lonely miles for it not to happen.

Hey, friends and readers,

After years of procrastination, I made a promise to myself that I would self-publish my Via Appia Book during the summer of 2020. But as I post this in the spring, we are all locked down in our homes. So I'm putting this out, chapter by chapter, in a bunch of places. I'll read it out loud on YouTube so you can listen to it while you wash the dishes or disinfect your house.

Check back here every week or so, and you'll find a new installment. Or better yet, subscribe and I'll email you whenever a new chapter is up, and give you links to the versions on YouTube and elsewhere. Best of all, when you subscribe you'll get a free copy of my travel notes.

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?

You're about to learn a secret about picking up Italian women. Or any women, really. This could probably work on men, too.

WARNING: Some of this story might qualify as Too Much Information. If you think so, you should probably skip it. You’ve been forewarned.

“Non e’ difficile,” said Francesco. It's not difficult. He was telling me how to get an Italian girlfriend.

Francesco had an eagle's head tattoo on one of his muscular arms. He stood beneath a “No Smoking” sign, rolling cigarettes and smoking them one after another.

“Irene, do you think I can teach this American how to pick up Terracina girls?” Francesco asked a young woman who was sipping a cappuccino. He pronounced her name ee-RAY-nay.

She put her hands together as if she were praying, and said “O Dio mio.”

For the next minute or so she looked at me, wide-eyed, shaking her head and her index finger, and mouthing the word “no,” while Francesco tried to impart his favorite observations and techniques.

Ask almost any Italian woman, and she’ll tell you Italian men are pigs. But the truth is, they’re the same as any guys anywhere. They’re just more transparent about it.

I wouldn’t recommend most of what Francesco told me that day in a bar in Terracina. But during my years in Italy I dated three--yes three!--Italian women.

If you're interested, you're about to learn a secret to picking up Italian women. Or any women, really. This could probably work on men, too.

You see, in Los Angeles, I'm just an ordinary dude who talks too much. But in Italy I'm a foreigner with an accent.

When someone speaks to me in Italian, I have to try really hard to follow along. Sometimes the only conversation I can manage is an awkward smile while I nod and say, “si’.” If I need to say much more than that, there’s a long pause while I struggle to remember the Italian word for peanut butter or how to conjugate the verb spalmare.

Apparently my weak language skills come across as intense concentration. My awkward pauses make me look thoughtful. To Italians, I appear to be a good listener.

It turns out many women can't resist a good listener, especially if he has a foreign accent.

Using my foreign accent mojo, I had once met a young woman who lived in a small town in central Italy. We were kindred spirits. In better economic times, she had traveled far, and had seen and done many interesting things.

She broke up with me over the phone about a week before I arrived in Italy to bike the via Appia. Then, the night before I started riding, she texted me and wanted to meet for coffee.

Now here I was, at the beginning of one of the coolest adventures of my life, and all I could think about was this girl. When I looked at Irene, and whenever I looked at just about any Italian woman on this trip, I was really thinking of her.

All I needed to do was alter my travel plans a little, and maybe I could rekindle an old fire. Would I call her? Or would I just keep going, and run away from another relationship?

I’m not an expert at this stuff, but I do have a litmus test. If the relationship makes you stronger, if the person helps you and encourages you to pursue your goals, especially if the two of you pursue your goals together, then you’ve found a winner.

If the person makes you feel insecure and confused, especially if that distracts you from enjoying the fulfilment of whatever really matters to you, then walk away.

On that day in Terracina, I didn’t know if I wanted to embrace the relationship or walk away. Maybe she didn’t, either.

As I write this now, I’m married (to someone else), and all those old issues have disappeared. I just want you to know the truth about my trip. I traveled across half of Italy with only half my mind and half my heart, because I could neither embrace nor let go of the relationship I was in.

If you ever do a solo bike tour, keep in mind that your emotional baggage will color your adventure in unpredictable ways.

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.

I want to help you experience the magic. Especially if you’re the kind of person who dreams about a journey like this, but you’re frightened to try.

overcome_obstaclesIt won’t be easy. It may take longer than you thought.

If you can do the one thing that you think isn’t possible, if you can cross that mountain range, it will change you forever. You will be able to do anything, and you will know it.

Some of the obstacles you think are holding you back will melt away as soon as you push back against them. Many of the things you fear and worry about will never materialize.

I'm going to help you overcome those obstacles. Let me explain.

If you’re a seasoned, confident bike tourist then I would love to have you along next spring. But if you think there’s some insurmountable obstacle that would make the journey impossible, no matter how badly you want to go, then this post is for you.

This post is for you if you’re interested in biking via Appia but you aren’t doing it because you think:

  • You can’t afford it
  • You’re too young
  • You're too old
  • You’re not in shape
  • You’re afraid of being in the wilderness in a foreign country
  • There is some other reason holding you back

You can do it. And I’m going to help you. Here’s why:

10 years ago, at the Leo Carrillo State Beach hike and bike campground, I met a man who took a group of developmentally disabled teenagers on a bike tour. They rode north from LA to San Francisco and across the Golden Gate Bridge, fighting the wind all the way.

Below Golden Gate Bridge

I met them on their way back home. The kids were confident and street-smart. I got the feeling they could go anywhere they wanted. And they knew it.

“The ride up was brutal,” the guy told me. “The only thing that kept these kids going was the idea of riding across the Golden Gate Bridge. You should have seen their faces when they finally did it.”

Ever since then, I’ve hoped to meet another person like that. Maybe it’s time to become someone like that, at least in my own small way.

So here’s the deal.

I’m going to do another bike tour of via Appia in May, 2017. I'm looking for people who have a burning desire to come along, but something is stopping you.

I will help you.

I can’t buy your plane ticket for you, but I can show you a number of ways to raise the money you’ll need.

I’m not a doctor or a physical therapist, but I can direct you to resources for strengthening your mind and body. In fact, if you think you’re not in shape for a trip like this, that makes two of us! We’ll hold each other accountable as we get in shape (and to tell you the truth, this tour isn’t superhard as far as bike tours go).

If you have a specific physical challenge that you think is going to stop you, I’ll look for someone who can build a bike that’s adapted to your needs.

I will personally coach you on getting into shape, making money, even learning Italian if that will make you more confident. We’re gonna make this happen!

Maybe you’re not especially interested in a bike tour of Italy. There’s still something in this for you.

Over the next several months, you’re going to hear stories of people overcoming their fears, their doubts, and their limits. Hopefully these stories will inspire you to do that one thing that you dream of, the one thing you think is impossible.

If you are interested in biking via Appia with me next spring, here are just a few of the things you’ll get to do as a result of this journey:

  • Tap into hidden physical and mental powers you didn’t know you had
  • Build lasting friendships with extraordinary people
  • Bring back stories and experiences that will change the way you look at the world
  • Grow stronger and healthier than you dreamed possible
  • Give yourself the classical education you always wanted

This journey will change you forever. I challenge you to join me. I dare you.

In fact, I beg you.

You see, by coming along on this trip, you’ll give me a chance to face down one of my own big fears.

Gravina in Puglia bridgeI’ve biked the entire Appian way from Rome to Brindisi already. I know enough about Italy and Italian to fix most problems that I can’t avoid in the first place. I’ve done bike tours that are longer than this.

But now I want to help you experience the magic. Especially if you’re the kind of person who dreams about a journey like this, but you’re frightened to try.

If I commit to helping you do it, then I have to face my own fear of failure, that maybe I won’t succeed in getting you to Italy and across the finish line.

But I accept the challenge. I will teach you to overcome any obstacle, and you’ll ride triumphantly into Brindisi like an ancient Roman noble.

Let me be clear about this offer, and especially what I am not offering to do.

This is not a free ride. I can’t pay for your airplane ticket or your AirBnB. (I would like to buy you a coffee, or maybe something stronger, while we’re in Italy.)

I’m not a doctor, physical therapist, or psychologist.

But what I do bring to the table is experience, creativity, a lot of good ideas and the will to help you carry them out.

Are you in? Fill out the form below, and we’ll be in touch.

I left out a lot of the loneliness, the confusion, the shameful and foolish decisions I made that still haunt me years later. I didn't tell you what I was really thinking about in Taranto, the last night of the journey.

When I re-read the first draft of my book, a lot of it just didn't ring true.

I sound like a pretentious schmuck who likes to brag about the places I traveled. That's a big part of who I was when I biked the entire length of the ancient Roman road, via Appia. But it's mostly just show.

In the first draft, I left out a lot of the loneliness, the confusion, the shameful and foolish decisions I made that still haunt me years later. I didn't tell you what I was really thinking about in Taranto, the last night of the journey.

Most of the emails I get about via Appia come from people who probably haven't done an extended solo bike tour. So I'm rewriting the book. I want to show you the dark side of pursuing a dream.

This book will still tell you where to go, what to see and do, where to eat and even advice on picking up Italian women.

via Appia gravinaq fountain

I'll give you good information about the route, in case you ever want to do a similar trip. You'll hear a lot of local history and stories, and you'll meet many of the Italians who made my journey unforgettable.

But I want to write something more than just a travelogue or a guidebook. So I'm putting back a lot of embarrassing things I cut from the first draft. Entries from my journal that will help keep it real.

This book is also my confession. I will share my deepest regrets about the journey. If I can help save you from some of the mistakes I made, this book will be worth writing, and hopefully worth reading.



If you're young and British and ready to get out and see the world on a bicycle, the Janapar Grant is probably one of the best things that could happen to you.

I'll fill you in on the details below, but if you can't wait, then here's the link: http://janapar-grant.org.uk/

The Janapar Grant was started by Tom Allen, after his own multi-year bike tour around the world (you can watch the film by the same name here

The applications are being accepted "In early 2016," but as of today all they have is a form where you can leave your email if you're interested.

All I can say is, if you are between the ages of 18 and 25, live in the UK, and don't have any work-related conflicts, you should be interested.

If you are accepted, you'll get all the equipment you need: bike, tools, panniers, tent, sleeping gear, and cook set. Better yet, you'll be mentored by some of the best-known names in bike touring, including Emily Chappell, Tom Allen, and several others.

If I qualified, I would jump on this. Just the application itself will get you thinking about your trip, planning, and sorting out both your route and your motivation.

Alas, I'm not British, and I'm nearly double the maximum eligible age. Still, old geezer that I am, whenever I set off on another journey I feel the same excitement and joy that I felt in my twenties--maybe more. Bike touring is a lifelong passion. But if you're reading this you probably already knew that.

Once again here's the link to the Janapar Grant:

http://janapar-grant.org.uk

By the way, what would happen if you didn't see this blog post and missed out on your chance to apply for the Janaper Grant?

Lucky for you, whenever I have a really important post, especially one that's going to improve the quality of your life, I email it to everyone on my tips list. If you're not on that list, you could have already missed out! Be sure to sign up below, or in the box to your right.

On a bike trip in Colorado, I got my butt handed to me on a Frisbee by guys who were 15 years older than me.

I blamed it on the altitude. And it's true that after a few days I could almost keep up with them. At least close enough that they mostly stopped making fun of me.

This was my introduction to middle age. I thought I was in great shape, but really I've been turning into a bike potato.

For years I scorned people who deliberately trained. "Just get on your bike and ride," I thought.

I also avoided any talk about racing. I'm all about bike touring, not racing.

Now I've done a bit of reading, and I learned the shocking truth: Bike touring can be an emasculating, power-sapping habit.  It can turn your strong, youthful body into a flaccid meat suit.

A physical therapist told me I should never do another bike tour again after the age of 40. I will not be following his advice.

If you're a stubborn fanatic like me, and you insist on bike touring, here are the dangers and how to reverse them.

Danger #1: Repetitive Stress Syndrome

If you take a short bike ride that lasts a few hours, you're going to gain a lot of physical benefits. Bike touring is different.

On a bike tour, you're in the saddle for hours on end. Probably six hours or more. Maybe 10 or 12 if you're a fanatic. I've done this on bike tours of Italy.

During that time, your back and shoulder muscles are straining to hold up your head. Your arms are locked on to the handlebars. Your knees are grinding along, over and over, with continuous pressure on the exact same spot.

In a more natural activity, you would be moving around a lot, using different muscles in different ways, shifting your weight around onto different joints, and generally stimulating and using most of your body.

On a bike tour, you're concentrating all the effort and all the strain. Many muscles are cramped far inside their normal range of motion. Other muscles aren't used at all.

Danger #2: Depletion of Your Reserves

bike tour california mountainYou have a limited amount of glycogen stored in your muscles and your liver. On an extended bike tour, you may not have time for your muscles to recover. Your glycogen may be used up without sufficient time to replace it.

When this happens, you might start burning protein instead. Keep this up for too long, and you can end up with a loss of muscle mass.

You may have noticed the skinny leg syndrome that some people have on a bike tour. Over time, you'll lose power and stamina because of the loss of muscle.

Danger #3: Inertia

If you're on a bike tour, you're probably trying to cover a lot of ground each day, and you'll likely have an interest in conserving your energy.

You're probably also thinking of the bike tour as a vacation, which means you'll be more relaxed.

These two factors have a tendency to make you ride more slowly. The problem is, you're essentially training yourself to ride slowly. A slow rider tends to get slower.

The Solutions

One of the most useful and practical bits of advice I've found is from Roy M. Wallack in his book, Bike for Life: How to Ride to 100--and Beyond. (see below) He suggests taking shorter tours.

This is great advice for many reasons. First, it minimizes the damage of the three dangers. If you're only touring for 3 days, a lot of the problems with bike touring simply won't have time to develop. It's also useful against the mental and psychological damage that bike touring can inflict.

Short tours are also more practical. You can fit them into a busy life. Do a weekend bike tour, and you won't have to miss work.

Better yet, you can turn a long tour into several short ones. For example, when I bike the via Appia next time, my plan is to ride for a day or two, then stop in one place and take a few days to really explore, talk to the locals, and have a learning/cultural experience while my body recovers.

One of my dreams is to tour around the entire Mediterranean sea. Realistically, my wallet and the geopolitical situation won't allow it. But maybe I'll reach my goal over several years, one country at a time. Turns out this will be good for my health, too.

Another way to defend yourself from the ravages of bike touring is to tour the way you train. Alternate long tours with short tours. Have days when you ride as fact as you can, or at least include sprints into part of your journey. Make a conscious decision whether to attack a hill all-out or to merely endure it.

Finally, add some cross training into the tour. Stop for a day and go hiking. If you're strapped for time, just do a bunch of push-ups in the morning, or take a 20-minute yoga break when you find a good spot along the route.

A bit of thoughtfulness will let you reap all the benefits of bike touring while avoiding the dangers. You may even finish the tour feeling fresh and invigorated.

Mentioned in this post:

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You can upgrade yourself and your situation by simply deciding on a new "normal." There are probably things you're not happy about, but you've been silently accepting them for a long time. They've become normal. What happens if you chose a new "normal?" Right away, you start thinking about how to make improvements. Things you took for granted are no longer acceptable. All kinds of clever ideas pop into your mind. And you feel a surge of energy to start implementing some of those ideas.

If you've done much bike touring, you're probably able to travel great distances on your own power. Very few people would consider this normal. You've changed the rules, and you're in good company. This is the secret to many great accomplishments.

Gravina in Puglia bridgeWhen Appius Claudius built the Appian Way, he had to take power by redefining normal. He broke so many rules that Roman historians complained about him, and his co-consul resigned in frustration.

But we still know his name today. And he set the stage for game-changers like Julius Caesar.

In fact, all of the extravagant debauchery of the later Roman emperors was made possible because each emperor went beyond what was considered "normal."

How to Change Your Life in 5 Seconds

You can upgrade yourself and your situation by simply deciding on a new "normal." Your brain is an incredibly powerful problem-solving machine.

There are probably things you're not happy about, but you've been silently accepting them for a long time. They've become normal. What happens if you choose a new "normal?"

Right away, you start thinking about how to make improvements. Things you took for granted are no longer acceptable. All kinds of clever ideas pop into your mind. And you feel a surge of energy to start implementing some of those ideas.

Here are three steps to help you get started:

Step 1: Define your new Normal

About a year ago, I asked myself, "Is it normal to sleep less than 6 hours a night and try to keep functioning by constant caffeine infusions?"

I had been reading about the bad effects that sleep deprivation can have on your brain, your memory, reflexes, the immune system, muscle growth, speed, and even hormone levels.

At the time, sleep deprivation was my Normal, and a good-night's sleep was the exception. I had to reverse this.

Step 2: Enforce the new Normal

For a month I made sure I slept for 7-8 hours every night. Some chores went unfinished. Some friends and family members may have felt neglected. But I was creating a new Normal.

When you enforce the new normal, you won't have to be a fanatic about it forever. Just get it established at the beginning.

Step 3: Don't stress the exceptions

Now I can go without sleep once in a while if I need to get things done. It's the exception, not the rule. The next day I'll feel tired and weak, irritable and confused, sometimes even nauseated. But then I remind myself that I used to feel that way all the time. It was normal. Now it's just weird.

Let's say you decide to bike a century twice a week, or study Spanish for 2 hours every evening. Once it becomes part of your routine, you don't have to worry if you miss out every once in a while. It will be easy to get back into the swing of things, because you've made it the 'normal' thing to do.

Challenge the Normal

What do you consider normal that you should re-examine?

Roman monument on via AppiaIs it "normal" to have a job that keeps you from spending time with people and activities you care about? Shouldn't it be normal to give yourself a full month every now and then to go on an extended long bike tour? Is it normal to have back pain, to eat junk food, to watch TV shows that don't really entertain you?

Are you hurting yourself by what you think is normal? Is your Normal holding you back? Who told you this was normal? Are you required to spend your life according to someone else's Normal?

I challenge you to redefine your Normal. It's a beautiful and terrifying power, and it's yours. You can do anything.
I'm almost finished with a book about bike touring on the Appian Way. If you would like to read the entire book, or even join me on a future bike tour of via Appia, subscribe below and I'll keep you up-to-date. Your email will not be published, and I will never share it with anyone.