In 2006 I became a cycling guide in Italy. I wasn't much of a cyclist and at the same time I was certain my passion for Italy and knowledge would be more than enough to lead clients through the region and give them a great experience.

After all, I basically served in this role in 1995 on my University campus and again in 2002 leading two friends on two occasions through Rome and Tuscany. I passed the Italian language test in order to work in Italy and so I assumed my language was at least "good enough".

I quickly realized my language was not nearly enough and on my first week off in Italy I went to language school. I loved being in school and staying in the stunning Sicilian town of Taormina. I loved being there so much I really hated that I had to actually go to work the following week. I was fortunate enough to be able to shadow my first trip in Sicily and watch 2 professional and talented guides do a job I knew, even at the time, I would not be able to do.

Within the first few days of my guiding it was apparent to me that I lacked a very particular skill for being a guide in a foreign country: nurturing. My colleagues, mostly female, were so naturally adept at putting the client first, even to the guides' obvious discomfort and frustration. I was amazed by the energy and stamina these women possessed, and I knew I was in trouble.

Why? Because I was in Italy! Italy was my place, my home for discovery, my soul-seeking enterprise and no client, no boss, and certainly no language barrier was going to get in the way of MY journey. I was in Italy, someone was paying me (very sparsely) to be there and I would be damned if anything was going to hinder my pilgrimage of self discovery. Of course this is hindsight. At the time I was a nervous wreck. Was I saying the right things, would I be on time? My head hurt so badly from dehydration, I was so tired, so tense, and without experience to show me when it would ease.

The very talented guides I worked with seemed to have limitless energy and almost a macho need to test their mental and physical capacities. If two talented guides worked side by side for the first time it was easy to see that they naturally competed to see who was the bigger martyr. Sacrifice was indeed the game, and I had no compunction to join nor any concept of the rules. From who swept the floor the most to who took out more trash, loaded more bikes, cleaned more dishes, read and wrote more notes; this was about the JOB.

Now, please know that I respect these talented folks enormously and this was the first job in my life where I faced the stark reality that on my best day I would NEVER and I mean that, be as good as most of these talented people. The problem was: I didn't want to be. I wanted something else. I wanted a menial job so that I could be there and learning, experiencing Italy. I simply needed to survive and for the first time in my life I did not feel the burn to excel.

Sure, I gave a few wine seminars while I was there and I cooked some outstanding food for the group. I loved doing these things because it was the only time in my whole experience that my colleagues saw that I was more than a useless sack. I was so slow at loading bikes, terrible with knots, nearly sub-human with verbal directions (always have been), and not even proficient with the language. I was working uphill all the time and so when clients needed me, I was not 100% present.

I remain guilty to this day and damned near regretful about my intolerance of clients. Yet, I should be grateful. Because it was the client that showed me I was not in the right place. I was most definitely in the right country, just at the wrong time doing the wrong thing.

This was most clear one bright morning in the Maremma district of Tuscany. There were always 2 guides on a bike trip. One guide would cycle while the other would drive the support van. On this particular day I was the cyclist; my favorite job in the world because I had 1 clear task, to manage the riders and chat with them.

We had taken a short break mid-morning after riding through the tufa rock town of Sovana. Some of the faster riders had gone out ahead and now I was about to join the main group of riders for the remainder of the journey. I was already very tired as the hills were intense and steep in this region and I had been forced to double back on a couple of occasions to encourage timid riders to get down the hills. As we all were exiting an excellent coffee shop in town I heard a guest say loudly to another guest "my God I really miss my Starbucks!" I was devastated. You can miss cheeseburgers, fast flushing toilets, self-serve gas, and drive thru food while you are in Italy. You are allowed to miss wide roads, big parking lots, and reality TV if you are inclined. However, when you are in Italy, you cannot be forlorn for motherfucking Starbucks. You are in the land of coffee pressed through the clouds of heaven and laid in your cup by Maestros descended from the Renaissance. I could only think to say vaffanculo! So I knew I had to go.

I told the group that I was going to go out ahead and catch the lead riders and I would meet them in a few at the next town. I waved goodbye as I put my map in my pocket and went down the nearest road that would lead me as far from anyone in the group as possible. I rode alone for 1 and a half hours in the beautiful iron-rich hills of the Maremma. I thought about my future and my past. I knew this was not what I wanted to do. I had just left a very interesting job as a wine cellar manager and consultant to come here. I had broken up with a girl to come to Italy and finally live my life here. Yet, that was not the expectation of the company where I toiled. They had no interest in my romantic notions or my arguments to let me create wine-based trips in Italy. I knew I was in the wrong place and so did the company.

At the end of that trip I was told of my very discouraging client ratings regarding my performance. I was not shocked, and at the same time I was crushed. I had just spent the previous 10 years of my life making customers happy with my work. I had made life-long friendships with many of my clients and so the idea of being disliked and in some cases, despised, was more than I could handle.

The company offered me another chance (albeit one set on a collision course with failure) to right the ship. Instead, I informed them I had seen the writing on the wall and asked would it be possible to help in another way as I was not going to succeed as a guide? The company seemed surprised and at the same time obliged and sent me on a great trek across France and Ireland to deliver a van and bikes. It was my greatest 10 days on that trip to Europe. Sadly at the end my money was stolen (see the story here) on my return from Ireland to Italy. I left Europe in 2006 with my tail between my legs. I was a beaten man who had failed miserably at something where I thought I would excel.

I knew I had done a poor job and it would take me several years and even another attempt in the travel business to know why. I am now on a path the resembles very much my lone ride through the hills of Tuscany. I am free to see what I see and to tell of its greatness and wonder. Working for the company in Italy taught me much more about who I am not, as it appears I already knew who I was.