High-class Hobo.

My most recent coaching gig was by far the most interesting yet—not for what I taught, but for what I learned.

As you may recall, my coaching isn’t usually for my boss’s clients directly, but generally for other coaches. In Eric’s business model, I am the life-coach-coach, the über-coach extraordinaire, sitting on high, hovering above his unworthy minions of real coaches. They’re the ones who have to go out in the world and actually meet the clients.

That usually means that I work at his office, doing internal training sessions a couple times a week. But my latest assignment was an on-site training for a very large French company with its own legion of internal coaching minions. So this was a big job, by far the most prestigious organization or venue I have ever been associated with.

As I was waiting for the attendees to assemble in the conference room, I had a hot chocolate (unfortunately not lubricated with the likes of Tommy’s stock of Bruichladdich) in the break room next door. I was standing at the window looking down on the street below when I spotted a navy blue Mercedes with tinted windows pulling up. The security guard in front of the building shot to attention and I knew that something special was happening. The door opened and emerging from the back seat was a man so important in the company that I recognized him from the photo hanging in the lobby. This was clearly the boss.

I went into the conference room and gave my presentation—an unexceptional affair for which my boss was paid handsomely. After bidding my farewells, I dashed for the door, trying to get over to Opera in time for a movie I was planning on seeing with Tommy. As I rounded the corner leading to the lobby, who did I physically run into but the CEO himself. I looked down and saw that the man I had just inadvertently thrown to the ground was Mr. Mercedes in the flesh.

He took it very well, but since I had spilled his coffee on the floor, I figured the least I could do was get him a new one. So we headed back to the break room. As we walked, I thought, wow, I’m about to have coffee with a man who rides in the back seat of a Mercedes, with tinted windows no less. I decided that Tommy could see Il Etait Une Fois by himself this time. After all, we had seen it twice already.

As we stood there in the break room, I visually examined Mr. CEO, up and down. He was the epitome of aristocratic France, from head to toe. From his glasses to his tie, from his handkerchief to his cuff links to his shoes, he was nothing but platinum, silk, gold and leather incarnate.

He asked the reason for my visit that day and when I told him, he politely refrained from deriding my business. He clearly was not the sort who would ever seek out the counsel of the likes of me and he was probably right not to. A proven captain of industry probably doesn’t have much to learn from a homeless drifter like me. And yet he was curious, wanting to know where I was from and what strange odyssey had culminated in me standing there before him. When I gave him the brief sanitized version of my story, he smiled and told me his.

What I discovered was that hidden underneath that €10,000 suit was a hobo just like me. At the age of sixteen, he had been sent to Montana to work as a cattle rancher for a summer. It was a cowboy dream come true. That summer, he was the envy of every Frenchmen he knew.

When his summer ended, he was supposed to catch a plane to New York, where he would connect with a flight back to France. But in those months in Montana, he had so connected with his new persona as a cowboy—an independent, self-reliant man roaming the plains—that he just couldn’t bring himself to fly east. Instead, he snuck into a railroad yard and hid in a grainer on a freight train heading east.

When the train stopped in Detroit, the bulls (the railroad police) caught him. He was dragged off of the train and into a makeshift train station. He had talked his way out of numerous strange situations during his summer in Montana and thought this was no different. But bulls can go either way, their attitude toward hobos shifting like the very wind that keeps the tumbleweed rolling across the open landscape where they wander. These bulls were in no mood for his stories. Sixteen-year-old Mr. Cufflinks was in trouble.

He spent that night in jail, staying up almost until dawn with the hapless bull charged with manning the jailhouse overnight. They ate, drank and played cards. In the process, the bull appreciated the company so much that he actually took a liking to this little Frenchman. At dawn, he released him, at which point Mr. Handkerchief promptly thumbed the first of many rides taking him east to New York, where he arrived in time to fly home, first class.

As I reflect on my encounter, I know that this sort of chance meeting must be just waiting to happen all around us. As you pass someone on the street who you think, based on meaningless superficial impressions, that you have nothing in common with, you may just as well be walking past your long-lost twin, your alter ego, without ever knowing it. In a city this size, go to any street corner or intersection with heavy foot traffic, stare out into the masses and just imagine the stories out there waiting to be told, that you will probably never get the chance to hear. But for now, I have to run. My movie is on again at 9:55.