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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.


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.


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.


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.


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.








Gold bars

Alchemy and bike touring













Mentioned in this post:


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.


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.


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.


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!



Ponte degli Aurunci arch






Via Appia Antica at Minturno. Photo: copyright Jacob Bear
Via Appia Antica at Minturno. Photo: copyright Jacob Bear




















Shaded road to Aurunci bridge


















This is an excerpt from the draft of a book I'm writing about a bike tour of the Appian Way from Rome, Italy to Brindisi. The full book should be available for download in late 2015. If you'd like a copy, leave a comment with your email and I'll let you know when it is ready. (Your email will not be published and I will never share it with other parties)

After I ride my bike into the hills for a few more miles, I see a huge fortress up ahead to my right. It’s just past sunset, and I know that if I want to explore I’ll have to stay in this area.

Roman milestone along Appian Way outside Itri, Italy

Where the road passes to the right of the castle, there’s a small town on my left. It only takes a few minutes to find a decently-priced hotel, and after some questioning I find out there’s good pizza nearby.

The decision is made. The hotel owner barely leaves off the conversation with her friends (all are sitting around a table covered with bread, coffee, and cigarettes) to get me registered, stash my bike in a back room, and welcome me to the town of Itri.

After a hot shower and pizza, some of the locals inform me that this town, Itri, got its name from the Hydra of Greek mythology, which Hercules fought in the swamps nearby. Hydra is often pronounced “Idra” or “Itra” in Greek and Italian, leading to the name.

Alessandra, who served me my pizza, told me that the castle was built up over a much older Roman edifice. There were a lot of battles over this spot, because of its strategic position on a mountain pass between two sea ports. She said the name of the town comes from the Latin word “Iter,” which means the route or the way, because of Itri’s placement on the via Appia. When I ask her about the word “Idra” she laughs and says, “That’s just mythology.”

When I’m done eating I wander around the castle in the dark. Much of the palace was demolished by allied bombing during World War II, but it’s still a vast labyrinth inhabited by scores of wild cats. Every friendly “Meow” sounds something like an Italian greeting of “Ciao.”

But the dark passageways and deep shadows are creepy, and I wish I had some company besides the cats.

Travel tip: Visit Itri on the festival “Day of Corpus Domini” (usually in June). The Itrani decorate the main street of the town with colorful mosaics made from flower petals. Almost better is the Olive Festival on the first Sunday in August. It’s a great day to taste olives, olive oil, olive bread, bruschetta, and of course there’s plenty of wine to wash it all down.


The modern road, SS7, zig-zags through switchbacks as it winds up into the mountains. Each time around, I notice the route coincides with the remains of an older, grass-covered road bed. This is the true Appian Way.

This is an excerpt from my new book, Tutto Nascosto: A Bike Ride Down the Appian Way. If you would like to download the entire e-book, leave a comment below and I'll make sure you get a copy. Your email will not be published, and I will never share it with anyone.

The archeologist in Rome told me my bike trip would be impossibile. Francesco assured me non e’ difficile. Leaving Terracina, I hope the journey will be easy but not too easy. It’s been a good bike tour so far, but I feel like I’m waiting for something to happen.

The ride out of Terracina starts to climb into the hills, and pretty soon I’m winding my way upward through a glittering jewel box of flowers, oak trees and olive groves. When I meet a farmer selling black olives on the roadside, I buy a whole bag and greedily devour them on rest stops.


The old road is undaunted by the mountain. It plods straight up the grade, unstoppable like the armies that used to use it. Riding up the modern road is challenging enough, but not daunting, and I’m thinking seriously about braving the weeds and stones of via Appia antica on my bike.

Traces of the Appian Way between Terracina and Itri
Park-preserved traces of via Appia

As if on cue, I wheel up to the entrance of an archeological park. Inside, I follow the usual basalt paving stones of the Appian Way, along with the remains of buildings from ancient Rome, the middle ages, and the Renaissance.

As in many places in Italy, the architecture here is a hodgepodge of different periods and styles. Each building is built up over an earlier one, and everybody borrows foundations, walls, and pillars from other buildings.

I got used to seeing this phenomenon everywhere when I lived in Rome. Much of the marble from the Colosseum, for example, was taken by the Barbarini family to build St. Peter’s square in the Vatican. Similarly, if you go into some of the older churches in Rome you’ll notice that the pillars don’t always match. This is because they were pilfered from different ancient Roman buildings.

As I ponder this, munching on salty black olives, I think how much our civilization, and even we as individuals, are collections of endless stories, ideals, influences and philosophies borrowed from different times and places.

As Bruce Lee was fond of saying, “Absorb what is useful, discard what is useless, and add what is uniquely your own.”

Perhaps my own bicycle quest is my unique addition to the long history of this majestic road and the beautiful lands it passes through. Think about your own journeys as you read this. What will you add to the world that is uniquely your own?
