Drifting With Darren Part II

As I shared this opportunity (to live homeless on the streets) with friends, some of them were afraid for me. Some wondered how I talked my wife into letting me do this, because their wives would never let them do such a crazy, potentially dangerous thing. My wife Tracy is a trooper and stood behind me 100%. However, that didn’t keep her from getting a little nervous the night before. She made me show her the clothes I would be wearing to make sure that I could blend in reasonably. She also made me go outside and test the clothes to see if they would keep me warm. After I took a stroll around the block feeling reasonably comfortable, I got her seal of approval. I had scavenged some old coats that had been donated to The Relief Bus for distribution to the homeless. I wore lots of layers and two pairs of boot socks.

I almost put off the adventure, because I was fighting a nasty sinus infection and I knew that the brutally cold weather could make it worse. I decided to take my antibiotics and steroids with me. Homeless people get sick too. Besides medicine and lots of tissue to blow my nose, all that I brought was a backpack with a journal, a pen, a MetroCard, some Chapstick and a copy of a book I was reading, Holiness, Truth & The Presence of God by Francis Frangipane. I also brought twenty dollars in my pocket for emergencies as Darren carefully instructed. I brought no wallet, no identification (which I later learned was a mistake), no smartphone, no computer or iPad. I did bring an old beat up cell phone to periodically let my wife know that I was still alive. This helped her be okay with the excursion. Actually I accidentally dialed her once while on the streets and she thought she heard a muffled “help” through the muffled phone in my pocket. Fortunately, she stayed calm and we talked soon after while I was loitering in Grand Central Station.

The night before I left for this unique experiment, I shared with my children over dinner what I was up to. Their obvious question was, “Why?” I explained that I wanted to learn just a little bit what it is like to be homeless, so that I could better understand their world. This would give me valuable information on how to serve them more effectively through my job at New York City Relief. I explained that I wanted to share what I would learn with our staff, board of directors, volunteers, donors and the church at large. My sons were a little shocked and said, “What other normal dad would tell his family that he is going to be homeless for two days?” It’s silly, but that night I tucked my sons into bed and kissed them goodnight, making sure it was a good moment together just in case it was our last.

Admittedly, I was putting myself into a vulnerable position, but I trusted Darren. He sent me this email to prepare me for the experience:


If we are still on for this special project that is to begin Thursday morning, there are a few recommendations that I feel would be best to mention to you. These recommendations are especially for your personal safety and well-being.

This is a special occasion, as you will be an insider, rather than an outreach worker working on the outside of the world that you serve. As an insider you will be privy to things that you would otherwise not see, hear and experience as an outreach worker. Also, as an insider, you are unfortunately privy to some of the hazards that homeless/displaced/transient/drifters occasionally suffer. These hazards can range from simple harassment to actual violence (though this is relatively rare, especially if you stay away from the more troublesome elements of the street environment). However, as an insider, the very same people that your charity provide assistance to – drug addicts, mentally ill, and ex-cons – are the very same people that could do you harm. They care nothing about how The Relief Bus has helped them in the past. As an insider you are fair game for anyone looking for an easy mark. You should be suspicious of everyone that you encounter during this event. It may sound jaded to you, but it works. How do you think I managed to survive and stay out of trouble for so long? It wasn’t by being trusting and trying to befriend everyone that I saw.

You are a very close friend and I will do my very best to ensure your health and safety. Maintaining your well-being during this special event is a personal responsibility to me. However, you must listen to me, as things that I will tell you during this special event will reduce the possibility of harm to you.

The following are some recommendations that will assist you greatly during tomorrow’s special project:

Inclement Weather: this special project of ours is due to commence in the midst of a particularly brutal cold snap that is currently gripping New York and the entire U.S. Northeast region. Because I am conditioned to survival in adverse living conditions in urban environments, I can withstand and have a very high level of tolerance for inclement weather. What others may consider cold, I typically only consider chilly. My breaking point for cold weather would likely be in the single digits or even somewhere below zero. However, when we are outdoors you will be cold. Very cold.

For your personal well-being I will try to limit our time outside as much as possible though there will be occasions during this unique event where you will be exposed to the brutally cold weather, particularly during commutes (which will be on foot) from one location to the next.

My advice to you is to dress very warm, this includes wearing layers and dressing in thermos if you have such attire.

When you are feeling really cold, think warm thoughts of warm places (i.e., home or a recent trip in a hot climate). Also, as odd as it may sound, talking to someone else (either in person or on the phone) or even talking to yourself (as odd as that may sound) can help because it distracts your focus from the cold.

I find that it also helps to remind myself that even if the weather in NYC is cold, residents living to the north in upstate New York have it much worse. For instance, if the temperature is 18 degrees Fahrenheit in NYC, its likely only in the single digits or even below zero in upstate cities like those of Buffalo, Albany, Syracuse and towns and villages along the New York state/U.S. – Canadian border. This helps to put things in perspective and allows me to admit that things could always be worse weather-wise.

Violence/Crime: though the likelihood is small to moderate, there is the possibility that you could be the recipient of a violent criminal action. To reduce the odds of such a woeful event befalling you, I make the following recommendations:

Bring the minimal amount of valuables necessary: if possible I STRONGLY SUGGEST that you do not bring your tablet. I also recommend that you leave your smartphone at home (use a “dumb phone” instead as they are less attractive items for thieves). However, if you do bring your smartphone, be mindful of who is around you. Some thieves will try and swipe your smartphone while you are distracted checking e-mails or text messaging while others will steal it at knife, or even, gunpoint. To reduce the potential of robbery, try to keep public displays of your smartphone to a bare minimum. Be especially careful at night. Bring only a very small amount of money with you that can be used in an emergency. I would recommend nothing more than $20.

Dress down as much as possible. The more you portray yourself as someone who has nothing of worth, the less your chances of being robbed.

A hygiene travel kit (especially toothpaste, tooth brush and deodorant) is also highly recommended.

Listen to me: I’m not the most street smart person but I have a high enough street IQ to gauge a situation and know if it is safe, potentially problematic, or even outright dangerous. If I tell you that you should not speak to a particular person or that we need to leave a particular area or situation immediately, you should take me at my word and not debate me. Remember, you have chosen to conduct this project with someone who is already street smart and urban survival savvy (me) to further enhance your own level of street smarts.

If you have access to pepper spray, I recommend you bring that along with you as well. In the past I have carried pepper spray (though I have not for a while). Though commonly a self-defense weapon for females, pepper spray also happens to be widely used by everyone from police officers to the Navy Seals in subduing unruly thugs.

Nonetheless, you should be relatively safe during our time together. Ironically, you have the brutally cold weather to thank for this. Cold weather keeps people off the streets; this includes everyone from law-abiding citizens to street thugs and knuckleheads (a common title for street criminals). Criminals don’t do well during periods of inclement weather and especially tend to stay indoors more during cold weather, which explains the typical steep drop in crime rates in northeastern cities during the winter months.

There may or may not be some harassment from police officers who want to throw their weight around just because they want to be jerks, though this is the least of our concerns.

Most of the information that I have provided here is only an overview of the most important issues that we may confront during this special project. I will of course, go into further detail when we meet up tomorrow morning. Overall, this should be a particularly interesting experience and it might be a life-changing one for you (though hopefully in a meaningful and healthy way). E-mail me if you have any concerns between now and later tonight. Take care.


Darren also sent me an email telling me that it wasn’t too late to back out. I love this guy. Armed with his suggestions, I headed to the city to join him, minus the pepper spray.

I met Darren at 7:00 am at the New Canaan Society meeting at the Brasserie Ruhlmann restaurant across from Rockefeller Center. We gathered with about 100 Christian businessmen to hear the weekly speaker. That week there were “energy groups” which are just small groups for discussion. I had been attending this group of mostly finance guys with Darren for a while, but this was his first time to participate in the energy groups. I wondered how he would like it. The topic was surrendering areas of your life to God and seeing him come through as a result. There were two Christian guys in the group and one seeker– all from corporate America. We went around the circle and shared. When it got to Darren’s turn, he very poignantly shared how he had become born again a year ago, but that he still had areas of his life that he had not surrendered to God. His honesty and vulnerability ministered to the man who was a seeker who reflected on what Darren had said. All of us drew closer to each other and to God through that discussion.

Before we left, I went into the bathroom and changed into some jeans with holes in them, an old sweatshirt and several jackets. We ventured out into the freezing cold and made our way to our second stop: Grand Central Station. We had enjoyed a muffin at New Canaan Society for breakfast, so we were good for food until lunchtime.

We hit the very cold streets and headed toward Grand Central Station. By the way, Darren wears no coat- only a fleece, a scarf and a couple of hats to keep himself warm. He really has acclimated to the bitter cold weather and can bear it much better than most. As for me, I was glad to be bundled up.

Grand Central Station was beautiful and bustling with people at rush hour. Darren informed me that Grand Central is the biggest train station in the world and that Penn Station is the busiest. He and I made our way to the food court where there were plenty of tables and chairs. There I saw many businessmen and women catching breakfast before they headed to work. Intermixed with the commuters were homeless people, mostly sitting quietly, just getting warm. Every few minutes a homeless person would come by and rummage through the trashcan looking for scraps of food that someone had left behind. Many were mentally ill.

There were homeless people who would also make the rounds begging for change from the business people. They didn’t ask Darren and I for anything. I asked Darren if he had ever panhandled, and he said, “Never.” It was way too demeaning for him to consider. I wonder what it does to a person’s psyche who does beg. Most people who beg get turned down nine times out of ten. How does it feel to be rejected over and over, all day long? I know that it is tough to get around in New York City without much money and asked Darren if he had ever jumped a turnstile to avoid paying subway fare. He admitted that he had and that he had once been caught and arrested. He made sure that it never happened again.

I noticed some people who were clean and well dressed, but who might be homeless themselves. One man in his sixties slept at a table, while a woman in her forties sat close and watched over him. She kept applying lipstick in copious amounts that extended far beyond the actual lip area causing a sort of clown effect. They appeared to have bought food from the pricey food court, but were camped out for hours after they had eaten. Darren said that some people who are homeless do an incredible job at looking put together so that no one would suspect the truth.

Police officers regularly walked around the food court and woke up any people who were asleep. I found that police and security do this everywhere in New York City. As you can imagine, this doesn’t make the police very popular with the homeless population.

Darren said that if they caught you in the bathroom shaving or brushing your teeth, they would kick you out. When I was in the bathroom, I went to dry my hands at the hand drier. A scruffy old man motioned me over to a better hand drier that actually had heat. He almost looked homeless himself, but was actually a security guard. He wasn’t the type who had a gun or even a walkie talkie, just a beat up badge pinned onto a very worn blue jacket. He started up a conversation with me about how he was going to try to get a better job working at a hospital. He explained that he used to volunteer at a hospital full-time to show them that he could work. This man, who was clearly on the bottom rung of the career ladder, evidently saw me as someone safe to talk to briefly about his future. I’m not sure why.

Before we left Grand Central, Darren took me to another bathroom where they had more powerful hand driers. He showed me how to fill my gloves and hat with hot air before heading outside into the winter air. These little tricks help him to survive. I did it and it worked like a charm.

I sat and talked to Darren, asking him about his life and daily routine. He doesn’t socialize with other transient people- ever. One of the ways he protects himself is by not connecting with anyone who could be a threat, either because of their mental illness, drug habit, or violent tendencies. Darren is very sensitive to avoiding being a target of the police or anyone else. For him, to associate with homeless people is to put himself at risk. He mostly stays to himself, and this is how he survives.

After spending a couple hours at Grand Central we headed to a soup kitchen for lunch. On the way, we stopped at the Port Authority bus station. Port Authority is the largest bus station in the United States. Many homeless people use it as a place of warmth and shelter. Darren showed me a large touch screen in Port Authority. It was a matching game in which you touch boxes that spin to reveal shapes. After playing a round very poorly myself, Darren pointed out that the high score of 12 seconds was his. He explained that it had taken him weeks of practice.

We walked fast that day, because it was bitterly cold. It was 17 degrees out, but with the wind chill it felt like 0. We hoofed it about 18 blocks between Grand Central and the soup kitchen, and boy was I glad to get there.


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