Cold City, Warm Hearts- Part 5 of STREET PILGRIMAGE

As I panhandled, I had to keep brushing snow off of my sign so that people could read it. That caused my gloves to get wet which then started to freeze. By the 45-minute mark I was shaking with cold and my hands ached. The snow turned to sleet rain which got my jeans wet so I held my sign over my legs like a roof. I only made $2.00 and 50¢ in that hour. It was going to be a long day…

homeless winter

I arose that morning at 5:30AM with a jolt. Another shelter resident was walking around the room saying “Good morning” loudly even though we didn’t have to get up yet. This inconsiderate behavior made me angry because I was exhausted and stiff from sleeping on a hard pew in the Bowery chapel. Why couldn’t that guy just shut up and let us get a few more minutes of precious sleep?

My resentment dried up quickly when I climbed out of my pew. There on the bare floor slept a man who did not get a mat to sleep on or even a pew. He must have come in late that night after the rest of us had fallen asleep. It had been a Code Blue night when people were allowed to enter at any hour due to the freezing temperature outside. I immediately felt bad for the man and guilty for taking his pew. I would return home at the end of the week, while he would remain on the streets struggling to survive. I felt deep sadness that anyone would have to lay their head down to find rest on a cold, hard tile floor.

I stumbled into the lobby to ask when breakfast would be served in the soup kitchen. I found out it would be several hours later and I didn’t want to wait. It had been a long night and I was ready to get out of there. Being crammed in a room with so many people can feel claustrophobic. I gathered my belongings and headed outside. It was pitch black and snowing. I hoofed it to the subway and made my way to Penn Station where I could get warm and use the public bathroom.

A decent bathroom is an oasis for people living on the streets and some of the only privacy that exists for them. You don’t realize how precious privacy is until you have none. Our psyches need a certain amount of peace and quiet in order to center and stabilize ourselves. I had always taken this for granted until this week.

After using the facilities, I headed out to panhandle in the snow. I couldn’t sit on the wet ground so I used some street smarts. I had seen other people make use of corrugated plastic mail bins as stools. One bin wasn’t strong enough to hold a person’s weight, but if you stacked up three or four it did the trick. I scrounged around and found some of my own to keep my butt off the wet concrete.

As I panhandled, I had to keep brushing snow off of my sign so that people could read it. That caused my gloves to get wet which then started to freeze. By the 45-minute mark I was shaking with cold and my hands ached. The snow turned to sleet rain which got my jeans wet so I held my sign over my legs like a roof. I only made $2.00 and 50¢ in that hour.

A couple of young women saw my condition and asked if I would like a hot breakfast sandwich. I said “yes” and they waited at a food cart for 15 minutes in the snow while the guy made it. I couldn’t believe how patient and persistent they were. They apologized for how long it had taken and I thanked them profusely. These little acts of generosity from strangers were magnified in the life of someone like me who was hungry for human kindness. A little compassion goes such a long way. I prayed for them after they left as I did for every person who gave to me.

I cried because of their compassion and I cried because I realized my temporary suffering was many people’s daily reality for years of their lives. God was breaking my heart.

Begging Cup

An old man put a dollar in my hand and looked me straight in the eyes. Another person did the same. I knew what they were trying to communicate to me. “I see you—I care.” I sat there, cold, wet and freezing, and cried. I cried because of their compassion and I cried because I realized my temporary suffering was many people’s daily reality for years of their lives. God was breaking my heart. I asked God for eyes to see and ears to hear so that I could learn. I asked the Holy Spirit to teach me and show me what he wants of me and New York City Relief so that I could obey.

I went into Penn Station to thaw out and eat my breakfast sandwich. It was SO good. They bought me orange juice too, which really hit the spot. All these encounters made me realize that every act of kindness matters. It lifted my heart every time someone put change or dollars in my cup. It reminded me of the verse, “And if you give even a cup of cold water to one of the least of my followers, you will surely be rewarded.”—Matt 10:42 NLT.

Many people wrestle with giving money to panhandlers—some because they don’t want to enable addiction and others because they fear that the person may be a con artist who isn’t really homeless. Others see panhandlers as lazy people who don’t deserve any help.

The New York Times featured a fascinating article on the subject titled The Pope on Panhandling: Give Without Worry. They reported on a perspective from none other than Pope Francis:


Living in the city — especially in metropolises where homelessness is an unsolved, unending crisis — means that at some point in your day, or week, a person seeming (or claiming) to be homeless, or suffering with a disability, will ask you for help.

You probably already have a panhandler policy.

You keep walking, or not. You give, or not. Loose coins, a dollar, or just a shake of the head. Your rule may be blanket, or case-by-case.

If it’s case by case, that means you have your own on-the-spot, individualized benefits program, with a bit of means-testing, mental health and character assessment, and criminal-background check — to the extent that any of this is possible from a second or two of looking someone up and down.

Francis’ solution eliminates that effort. But it is by no means effortless. The pope said that giving something to someone in need is “always right.” (See photo below of Pope Francis visiting men at Vatican homeless shelter)

But what if someone uses the money for, say, a glass of wine? His answer: If “a glass of wine is the only happiness he has in life, that’s O.K. Instead, ask yourself, what do you do on the sly? What ‘happiness’ do you seek in secret?” Another way to look at it, he said, is to recognize how you are the “luckier” one, with a home, a spouse and children, and then ask why your responsibility to help should be pushed onto someone else.


Then he posed a greater challenge. He said the way of giving is as important as the gift. You should not simply drop a bill into a cup and walk away. You must stop, look the person in the eyes, and touch his or her hands.

The reason is to preserve dignity, to see another person not as a pathology or a social condition, but as a human, with a life whose value is equal to your own.


It is completely amazing to me that this man who leads his own country as well as one of the largest religious organizations in the world (1.2 billion), understands the importance of touching a beggar’s hand. I learned this firsthand and can confirm that he is absolutely correct on that point.

I can also state unequivocally that panhandling is not easier than working a job. I have worked many menial jobs, including manual labor, in my life and begging is the absolute worst “job” I have ever had. It is a wretched state to be in. Sitting for hours with a cardboard sign isn’t living, it’s a slow death. You turn your emotions off and simply become numb to life. You are in public view, laid bare on the altar of public opinion. Your shame is on display for the world to see. People don’t beg to get rich. They beg because they don’t believe that they have any other option. They exchange their self-respect for people’s pocket change. It is a demeaning existence and you can’t get much lower.


Many people have told me how they were offended by beggars who turned down the offer of food and just wanted money instead. Hard to believe, but people need more than food to survive. In this video story by Invisible People, a young man named Andy who is homeless in Wales describes how people constantly give him food when he is desperate for money to get a room.

A good Catholic friend of mine (see a trend here?) was talking to his priest about the dilemma of whether or not to give to beggars fearing they would buy drugs or alcohol. The priest said that the greater risk was not about giving money to someone who might buy alcohol or drugs. He said that the greater risk was missing the person who genuinely needed money for food, shelter or other essentials. That perspective informed my friend’s approach from then on.

I will not tell you that you should give money to every beggar or that you should ignore every beggar. I advise you to take a moment and pray when you see someone begging. Ask God how you can connect on a caring, human level with that person.

One time while walking through New York City with my daughter Hailey, I passed a woman who was sitting on a piece of cardboard on the ground and begging. I got halfway down the block when I heard the voice of the Holy Spirit in my heart telling me to go back because I was about to miss Jesus. I turned around and we went back to talk to the woman. I offered to buy her a meal. She only spoke Spanish, but through my Spanglish I learned that she was disabled and had pain in both of her legs. She had several children and was in a very tough place. My daughter and I gave her whatever cash we had and prayed with her. It did not solve all of her problems, but it was love in action. It was also a test of my obedience to God. Prayer opens a door for God to take over when I come to end of my abilities. Our act of faith can trigger the supernatural. I can’t help but think of the boy who gave Jesus his lunch of bread and fish that ended up feeding thousands. The holistic approach of giving materially and spiritually is how Jesus operated.

Living on the streets changed the way I treat people who are panhandling. At the outreaches we operate at New York City Relief we have a policy against giving out money. We have found that money can get in the way of building relationship and connecting people to resources at our weekly outreaches. In the context of outreach we have found that it is better to connect people to social services and empower them to take their lives back. The relationships we build as we journey together grease the wheels towards freedom. I applied this to my personal life as well and never gave out money. After living on the streets for a week, I changed my tune.

Now, when I am walking the streets as an ordinary citizen, I try to stop and acknowledge every person I see who is begging. I ask them their name and if I have a dollar, I give it to them. In this context, I find that generosity can open a door to relationship. If I don’t have a dollar, I just tell them that I don’t have any money on me. Whether I give them money or not, the people always respond to my friendly smile with another smile. I ask a few questions to get to know them and offer them a New York City Relief connection card. They always appreciate the kindness and offer of help. We usually close our time together with a prayer.


Connection cards are little cards (see outside cover left) with all the information on where and when people can get food and help at one of the many weekly outreaches operated by New York City Relief. Want to have some connection cards of your own? Click here to download and print your own.

Many people purposefully carry pairs of socks or hygiene kits in their purse or briefcase to bless someone they may meet in their daily travels. This is brilliant, because these are some of the items most needed by people struggling with homelessness. They are much appreciated and can lead to some wonderful moments connecting with people. In the spirit of “do unto others”, rather than buying the cheapest socks available, why not buy the best quality socks you can? For every pair of socks you buy from a company named Bombas, they give away a pair of socks to someone struggling with homelessness. Win-win! Another great option is to carry gift cards to give out that allow the recipient the dignity of choosing their own meal at a local restaurant.

If you want some helpful tips on interacting with people challenged with homelessness, my friend and Vice President of Outreach Operations at New York City Relief, Josiah Haken gives his Top Ten Homeless Outreach Tips here.

Let’s get back to my street pilgrimage living on the streets of New York City…

St Lukes soup kitchen

I stayed warm that day by taking shelter at Grand Central Station. I ate a delicious lunch at St. Luke’s soup kitchen (See photo at left). The volunteers were friendly and fabulous. A homeless woman I met there was named Sierra. We had a very nice conversation over our meal. Some of what she talked about was delusional and strange, while much of her conversation was intelligent and lucid. She was a sweet person. I told her I was going to get a second coffee in a minute. While I was getting my stuff together to leave she came back with a second tray of goodies for herself and coffee for me. I told her she was very sweet and that I enjoyed talking with her. I took the opportunity to tell her about the women’s shelter at New York City Rescue Mission. She didn’t know anything about it and was glad to get the info. I also gave her a New York City Relief connection card and told her how helpful those people were.

Throughout the day I continued to encounter people living on the streets who were struggling to keep a grip on reality. Read more in the next article in the STREET PILGRIMAGE series titled, The Trauma Of Homelessness…

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