As a New Yorker, I’m used to the spiel. “I’ve got these kids who need …” or “I need money for …” or simply, “can I have a dollar?” Usually, all but the last are total BS, so it is easy to brush them off and say, “sorry, I’m broke too.” This time was a little different. Instead of starting with the story, he started with an introduction.

“Hi, I’m David,” he said, as he stretched out his hand.

Such a simple gesture, one that you might see just about anywhere else, but rarely do you find with a disheveled man on the street, smoking what seemed to be the butt of a cigarette.

My first reaction, of course, was to step away. Not because he was (potentially) homeless, but because I have a horrid aversion to cigarette smoke. I think having been a smoker myself, once upon a time, has given me a super sensitivity when it comes to burnt tobacco. That and a general fear of the asthema that it inevitably triggered causes me to avoid even a hint of the stuff. The irony of how staunchly I used to ignore my own cigarette smoke as I pushed it on others was not lost on me as I almost reflexively backed away.

Feeling slightly ashamed, I reversed positions and met his hand with my own. “I’m Drew,” I said in return.

Then came the story. He began to relay to me about how he had just been released, was still trying to make his way, and was hoping I had some change. It wasn’t much different than the thousand stories I had heard before, so reflexively my inner New Yorker came forward and offered, “sorry, but I’m broke too.” Almost as an aside, I added, “I don’t even have a home of my own right now.”

Not entirely true, but if there is one thing I can say about myself, it’s that I have a penchant for dramatic statements.

So then he started talking. He asked me where I’m staying. He told me that I look like a smart guy, the kind that likes to read. Not that fantasy or science fiction crap, but good heady stuff.

He asked me if I had ever thought about starting a business.

I told him I had.

He leaned in, whispering to me as if he was going to suggest something elicit that no one else should hear, “you should start a travel agency.

Confused by the juxtaposition of how he told me and what he told me, I must have given him a funny look. He explained further. A lot further.

“See that over there?” He pointed to the building across the street, though, I think his intention was just to point in the general direction of the docks several blocks away. “Think about all those boats, what is the easiest way to go on vacation? You take a cruise.”

While I mostly disagreed with his point, I didn’t really get a chance to object as he continued on. “If you were to start a travel agency, you could make bank around here. You open one up on every corner. Different names, all around the country.” Seemed more like a Ponzi scheme than a business, but I listened on.

“Think about all the hotels. They sell a room for $100, you get it for $30, that’s pure profit. Or hell, maybe the room is $300 and you get it for $75. I don’t know what the prices are like, but you get my point?”

His math definitely made sense, however, I was starting to wonder how long he had actually been incarcerated and I wanted to ask, “have you ever heard of the internet?” But instead, decided to keep that one to myself. His heart was in the right place and I enjoyed that he honestly thought he was helping out.

Unfortunately, I had to leave and decided it was time to brave the rain.

Before jetting across the street, I said to him, “David, it was great to meet you. I’ll definitely take your words under advisement. Have you ever thought that maybe you should start a travel agency? Best of luck if you do.”

And I was gone. I didn’t want to be completely rude, but the fact was, I did need to get back to work, even if work was just in the coffee shop down the street.

As I hurried down the opposite sidewalk, I heard David shout to me as he shadowed me from the other side. “Hey man, best of luck. My name is David. I’ll see you again.”

Taken out of context, that could sound creepy, but I think he genuinely thought we’d talk again some time. Maybe we will. Maybe he’ll take his own advice and start a travel agency. The idea was out of date, but at least he had some enthusiasm and zeal for it. In the end, that is all that really matters.

I’m a father, traveler, and web developer @Automattic. In the wee hours, I’m also working on new projects like 1 on 1 Questions.

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