Skip to content

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.

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.

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?

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 there's a story in you it sometimes might be better to let it ferment. Seal it in the oak barrel for a few months, bottle it an store it in your wine cellar until it's a properly aged vintage. I'm giving you the highlights, concentrated and distilled over ten years, and if it stuck it's probably important.

mediterranean_mosaicIt has been ten years since I biked the via Appia, and I'm only beginning to get serious about publishing the story.

What kept me so long? Excuses, hundreds of endless lame excuses.

And yet if there's a story in you it sometimes might be better to let it ferment. Seal it in the oak barrel for a few months, bottle it an store it in your wine cellar until it's a properly aged vintage.

That's what I did with this story and now I might have something worth reading. At least I have something worth remembering, because after all these years the best parts of the story are the only ones I can really remember.

Anything that has fallen away was almost surely less important. I've waited ten years to give you just the highlights.

In fact, one of my big frustrations in writing this book is that it's been too short. There isn't even one tiny thing to add in here that could make it longer without somehow ruining the book.

I tried for months to pad the book with extra words, new ideas, more plain old stuff but sometimes less really is more.

Are people going to pay the same price for an 80-page book as they would for a 200-pager? Maybe more. I'm giving you the highlights, concentrated and distilled over ten years, and if it stuck it's probably important.

The good stuff always sticks.

I've got a manuscript that's been commented on and rewritten and is nearly done. But I want to do this right. That means an audio version, proper formatting, and  professional  editing as soon as I can afford it.

In the meantime life gets in the way. I'm building a bathroom. I'm helping a friend sell his house. I'm caring for neighborhood trees and eight (yes, eight!) cats and writing all the copy for a website for one of my clients.

In a few weeks I'll be looking for a job.

But all that said, I'm still going to get this book published someday some year. And you'll be (hopefully) around to read it when I do.

1

It's about following through on your dreams, no matter how late and slow you are, and no matter how foolish the dream. That must be it. Be the architect of your own fortune, better late than never.

In trying to publish a book about the via Appia bike tour, I'm following James Altucher's Ultimate Guide to Self-Publishing.* He has a checklist of 20 items meant to get you through the whole process, from the idea to the finished product.

I'm hung up on step 2.

The first item on the checklist is, "Write every day." Over the past six months, I've been close. Now I have a calendar in front of my computer where I get to put a yellow slash each day I write, and the number of days in a row.

It's heartbreaking to get to 30 or 40 days, then skip a day and have to start over again at zero. This keeps me motivated. This might be a good training tip, come to think of it. If you're getting ready for a bike tour, and you want to exercise every day, you could use this same process to stay on track.

But that second item on the list is a killer, at least for me: "Decide what the book is about."

There's an easy answer, or at least an obvious one. It's about a bike tour of the ancient Roman road, the Appian Way. But I want the book to be about more than just this.

The book is about pursuing your dreams. Pyrrhus shows up a lot in my story, because he had a dream of becoming rich and powerful by conquering sections of Italy. He was essentially stopped by Appius Claudius, the builder of the via Appia who famously said, "Every man is the architect of his own fortune."

Appius Claudius had a dream of building aqueducts and roads that would make his name immortal. He achieved all this relatively early in his career.

Claudius and Pyrrhus were notorious for their ability to "just do it." When they had a dream, they would go for it.

I'm not a Pyrrhus or a Claudius. I first stumbled onto via Appia while trying to walk off a hangover after a night of partying in Rome. That very day I fell in love with the road and the idea of taking a bike tour along her entire length.

It was seven years before I did anything about it.

But it turns out it truly is better late than never. I did follow my dream, however belatedly, and I made that first bike tour seven years after I first got the idea.

Now the new dream is to write a book. Or rather, to publish it. I've been writing for years. A lot of the manuscript came directly out of a journal that I kept during the bike tour, a bunch of papers held together (ironically) with rubber strips taken from old inner tubes.

I think I've got a decent manuscript for the book now, but what is the book really about? I want it to be meaningful for someone who never plans to do a bike tour in Italy.

It's about following through on your dreams, no matter how late and slow you are, and no matter how foolish the dream. That must be it. Be the architect of your own fortune, better late than never.

Step 3 in Altucher's Checklist is simply this: "Write it well." Fair enough. I think the first draft is decent, and I've generally gotten good reviews along with a lot of constructive criticism from people who've read the manuscript.

But can I really write it well if I'm not clear on what the book is about?

It feels like I'm at the beginning of a steep hill at the start of a long bike tour. I'm in the lowest gear standing in the saddle, just to get past steps 2 and 3 on the checklist.

There are 20 items I need to check off in total. Maybe in another seven years I'll be able to tick them off and be a self-published author.

Here's the good news. Becoming the architect of your own fortune is just like pushing yourself forward on a difficult ride. You'll get there.

I can almost guarantee you'll get there faster than I will.

This was a rant about my new book on biking down 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.



*I didn't include a link to James Altucher's guide at the top because it's not as simple as going to Amazon. As far as I know, James will give you the book for "free" but you have to pay for a subscription to his newsletter. Alternately, you can download the checklist at no cost in exchange for signing up for his email list. That said, I'm a paid subscriber and a big fan of James Altucher. If you're interested in quitting your job and having more time for bike tours and other things you love, I recommend reading his stuff. Just be ready for a sales pitch. Here's the link (Once you're there, scroll down a bit if you just want the free checklist.)

I've got a book title. Here's how I did it.

Bike touring can mean a lot of different things.

For months I agonized over what I really wanted to say in this book. I wondered whether it was even worth putting out there.

I know I didn't want to write another travelogue. I hope if you'll read it you'll set out on many glorious journeys of your own, but I can't expect you to care very much about mine. I tried to serve up nuggets of history, tips, and suggestions seasoned with a sprinkling of local color and personal experience.

What finally came out was a big surprise.

bike-tour-colosseumTo make a long story short, I finished the whole thing but I didn't know what to call it. So I let the public vote with their clicks.

The rest of this post is about how I did it. If you've ever thought about writing a book of your own, the rest of this post might be useful. If not, then you can skip it. Save your time, and go for a bike ride instead.

How to Select a Best-Selling Title for Your Book

I had a lot of things I wanted to say in this book, so it was easy to come up with over a dozen titles. The first step was to narrow it down a bit, so I talked to a lot of people and threw out the titles they thought were the worst.

I finally pared it down to these three, which are pretty straightforward:

Biking the Appian Way
Biking via Appia
Biking Rome to Brindisi

I paired each one of these with a subtitle, and repeated them without the word "biking."

Next I created a google adwords campaign.

If you've never done this, it's pretty simple. You start by picking a batch of keywords. I used things like "bike touring Italy" "ancient Roman roads," and the names of various cities and towns along via Appia.

Once you have your keywords, you create your ads, which have a main headline and two subheadings. I simply used my titles and subtitles, and I was good to go.

When people search for your keywords, a lot of them will see one or more of your ads (Google shows them at random). You get data showing how many times an ad was seen, how many clicks it got, plus a lot of other useful information.

One title and subtitle of mine got nearly twice the clicks of any of the others. Within days, I had a winner:

Biking Rome to Brindisi: How traveling the ancient via Appia saved me from a life of quiet desperation

If you want to read the pre-publication edition, contact me by leaving a comment below.

A heavy block of lead was dumped on me this week. My first response was to take the concept of "temper tantrum" to a whole new level. But my wife convinced me to take a hike with her, talk things through, and look at new possibilities.

About two hours later I had turned the lead into gold. Here's what happened.

My latest quest is to finish the via Appia book, get a cover designed, record the audio version and upload everything to Amazon. I was all set to do this over a small vacation later this month. But my employer had other ideas.

I was offered an "opportunity" this week. Terrible things will happen to a lot of people if I don't accept the new responsibility.

Now the vacation has been postponed to December, but that's not all. Over the last few months I've managed to set aside an hour or two to write each day. Now I'll have to use that time to plan and prepare for my new job "opportunity."

However, I'm not complaining anymore. I'll get the book finished a little bit later than planned. More importantly, I've figured out some ways that my new job responsibilities (which don't come with any additional money by the way) can actually help me finish and promote the book. This may even help me get more time for bike touring in the future.

The lesson here is not "buck up." The lesson is "transform."

Gold bars
Photo: "Gold Bars" by Agnico-Eagle - Agnico-Eagle Mines Limited. Licensed under CC0 via Wikimedia Commons -

Alchemy and bike touring

A long long ago, there were wizards who could turn lead into gold.

At least that's the old popular legend. The modern popular legend is something like Paolo Coelho's famous book, The Alchemist. The hero has a dream, and he goes out and pursues it. I won't spoil the story, but let's just say if you're interested in bike touring you'll find a lot in The Alchemist that will resonate.

If you're reading this, you're probably on a similar path, chasing down a dream. Or you're going to be there soon.

But sometimes heavy obstacles will come along and block you, or weigh you down. Just when you're close to the goal, annoying things like recessions, back injuries, and broken spokes get in your way. They'll trip you up every time. Which brings me back to alchemy.

The obstacles are the raw materials that refine you and shape your destiny. They are the painful chunks of lead that you will turn into gold.

You've probably run into a problem before. If nothing else, think about when your bike broke down in the middle of a ride or worse yet in the middle of a tour. You probably figured out how to fix it. You'll get amazingly creative on a bike tour.

Better still, whenever you sacrifice comfort and convenience, you are compensated with adventures and discoveries. This is what happened to me at work this week.

And this is what brings me to the real secret of alchemy.

You're always going to run into problems. Even when you're not trying to travel hundreds of miles balanced on this wheels and propelled by nothing but your own force of will.

Bike touring is a great way to train for all the rest of life, because you have to deal with whatever happens, and you'll usually come out better off. If nothing else, you'll have a good story to tell everyone over dinner.

If you remember this, you can develop superpowers. The next time you're dealing with petty, frustrating people, you can think back to that broken chain link on the mountain pass, or the wrong turn you didn't discover until two hours later.

The troubles and obstacles you encounter in life are the lead, the gross matter that you can transform. The unexpected rewards, maybe the act of transformation itself, are the gold.



Mentioned in this post:

2

Archeologists will never finish scraping the ancient world out of the soil and gluing it back together, but there's still an energy you can feel when you're alone in these ancient places. I wanted to see marble columns rising out of misty fields in the dawn, and remember what the Romans forgot when they became too powerful as a civilization and too weak as individuals. Surely one enthusiastic biker could make the journey.

I have a gift for you, and a small favor to ask in return.

This post is the first chapter of my new book on biking the via Appia. Do you want to read more? Do you have any suggestions on how to make it better, or do you think I should just scrap the whole project? Please leave a comment at the end of this post, and tell me what you think. Roman monument on via Appia

Chapter One: Impossibile

Once upon a time, a happy nation of farmers and artisans and philosophers were all going to die.

A ruthless Greek general was trampling over Italy with an army of nearly thirty thousand warriors, horses, and elephants. Fields were burned, slaves were taken, and one by one the tribes and colonies surrendered to him, or even joined him.

But in the nick of time, one grumpy old man stood up to the bully and called his bluff.

Old Appius Claudius wasn't usually a hero, and the history isn't as black-and-white as I'm presenting it. But in the speech that rallied young Rome against her enemies, he said, “Every man is the architect of his own fortune.”

This book is mostly about you and me and becoming the architect of your own fortune. But I promise I'll get back this story and tell you more about the general, the elephants, and especially Appius Claudius.

Above all, there's one thing you need to know about Appius Claudius.

The speech was one of his last public acts, but he is better known for one of his first. When Appius became Censor, he nearly bankrupted the treasury to build a road into the uncertain wilderness of the south. And as the keystone of a career that was built almost entirely on sheer chutzpah, he named the road after himself.

Two thousand, three hundred and seventeen years later, on that same road, every motor vehicle in Italy was trying to mash me into pesto.

Just after the via Appia leaves Rome through the Porta San Sebastiano, the shoulder disappears. Two brick walls guard the road, turning it into a roofless tunnel where every cyclist is at the mercy of every driver.

Commuters in Fiats, late to work, pronounced vulgar curses against my ancestors. Produce trucks threatened to scrape me against the walls, an olive between two millstones. Tour buses nearly crushed me like a bunch of newly harvested grapes.

Soon I would be ground apart and made into pesto, olive oil, and wine. 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 with the fact that a sweaty American, wearing shorts and clutching a bicycle helmet, would enter his office this early on a weekday.

In my best Italian I told him I wanted to ride the via Appia Antica from Rome to its end in Brindisi. From the surprised confusion in his face, you would think I had just volunteered to be a nude model for his next marble sculpture.

"Impossibile!" he insisted, 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 biker could make the journey. I had already decided to make the trip, with or without anyone's help. But I wanted some advice from an expert, if I could get it.

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

Dr. Grillo assured me that it could not be done. Much of via Appia was buried on private property. He mentioned floods and swamps and mountains. Also many places where we simply don't know where 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 the Mediterranean, ancient history, and the desperate need we have (I think) in the USA to rediscover some common roots.

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

Grillo understood. Or at least I think he had stopped deliberating whether 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're exposed to the people and the energy of the place. You drink in the nectar of the world, and anything is possible.

Italians all gifted with a powerful intuition. Even if you don't know the right words, if you speak with passion many of them will read your mind and give you exactly what you want. As I spoke, my new archeologist savior was already opening drawers and pulling out topo maps, old photos and drawings.

When I finished, he gave me a stream of directions and names and numbers in rapid Italian. I frantically scribbled as much as I could understand in my notebook. I wasn't looking for perfection, I told him, just adventure and fun and new learning and experience. If I couldn't retrace all of the Appian Way, I would still see most of it, and do the best I could.

Dr. Grillo assured me once again that I was attempting something impossible. “Le machine ti pestaranno,” he warned. The cars will pound you into pesto. That's good. I'll use that.

He shook his head, and shook my hand. “In bocca al'lupo,” he said. In the mouth of the wolf, a Roman way of saying “good luck.”

“Creppi lupo,” I replied.

There’s something in human nature that won’t let us stare too long at an unclimbed mountain, an uncharted wilderness, or an unanswered challenge. This is why people skydive and sail across oceans.

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.

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, “You’ll destroy your arse in the first 10 kilometers.”

A crotchety old park superintendent muttered “E tutto nascosto.” It's all hidden.

Everything they told me was true. The Appian Way is fraught with peril, a 400-mile gauntlet of knee-grinding climbs, bone cracking pot holes, 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. You’re going to find the secrets that are tutto nascosto, hidden away in your own heart.

A journey like this is going to change you. It must. There are too many lonely miles for it not to happen.

If you enjoyed this and you think I should write the rest of it, please let me know! I'm also open to suggestions on how to make this book better.

FaceBook: https://www.facebook.com/AppiaBike
Twitter: https://twitter.com/TheJacobBear

If you want to get the latest updates on the book, the journey, and lots of juicy bits on how to be the architect of your own fortune, sign up here:




Thanks for reading!

Jacob