Challenges I face in my encounters with the homeless on the streets of New York
Photo credit: pixabay

The Art of Seeing  – by Michael Milton

I feel a vague unease when I am approached on the street or subway by a homeless person. Not fear, exactly. My disquiet is a recipe made up in unequal measures of several panicked and somewhat irrational thoughts:

Homelessness can happen to anyone, even me; I can’t afford to be giving my money away!”

What if they only use the money I give them to buy drugs or alcohol?”

Maybe better than giving cash, I should slip into a deli and buy a sandwich for them.”

And then, my least favorite but arguably most powerful ingredient in this face-to-face-with-homelessness brew is, “Perhaps, I ought to simply have a conversation with the individual and see where that goes.”

Photo credit: Flickr

And the idea of actually speaking with the homeless brings on a whole new cavalcade of thoughts:

What if we talk, and they become attached to me and I can’t get rid of them?”

What if they ask where I live?”

“What if, in guilt-ridden panic, I end up giving them not fifty cents but fifty dollars?”

(It is important to note that none of these scenarios have ever come to fruition.)

In fact, the closest I have gotten to the conversation phase with a homeless person is a quick glance in his or her direction accompanied by an overly toothy smile and a mumbled “Good luck,” or “Hope you are feeling better” as I slip a handful of coins into a coffee can on the sidewalk.

I want to make a connection. I do. I want to be free of the judgments and fears that rise up behind my eyes in these ever more common confrontations. I want to gaze at another—homeless or otherwise—and offer up twin pools of compassion and caring.

Anyway, that’s my goal. It is a particularly over-sized goal considering that a part of me still thinks that homelessness is contagious, like tuberculosis, as easily picked up in conversation as from the metal grip bars on the 1 train.

I meditate at a Buddhist zendo in mid-town Manhattan. Recently, one of the teachers or sensei told a story about a homeless man he knows from his neighborhood. Our sensei never actually used the word, ‘homeless,’ in his story. Instead, he said, “My friend Jason sometimes lives in front of Starbucks and then sometimes he moves over to a cardboard box near the dry cleaners.”

Our teacher went on to say that he always stops and has a conversation with Jason, talking about normal things like the weather or the construction going on across the street or the loud sirens heard earlier that morning. Then, he gives Jason money–a dollar or two– and continues on his way.

The other day as their conversation was winding down, sensei opened his wallet and discovered he only had one twenty-dollar bill.

Our sensei serenely gazed out at all of us gathered at the zendo for his weekly talk and said: “And when I made this discovery, I paused.”

Photo credit: Maxpixels.net

I’ve often been in similar situations myself. In my neighborhood–at the corner of West Seventy-Ninth Street and Broadway–there is a tall, thin man who I have judged to be slightly mad; he flaps his arms and raves to one and all about a whole slew of topics, ranging from the deleterious effects of racism to the idiocy of horn honkers.

On a temperate day, he “lives” on the bench in the center-divide of Broadway. And when it rains, he relocates to a slightly more protected few square feet next door to the neighborhood smoke shop where I buy my Lotto tickets. One week, on a drizzling morning, he was standing on his protected patch of the sidewalk asking for money as I emerged from the shop. I had just won ten dollars and already greedily stuffed my loot into my wallet.

Spying him, I sped up as I headed north. “I’ll catch you next time, man,” I muttered in what I think is a city-cool, off-handed kind of way. I already knew I only had an assortment of fives and tens and twenties my billfold, no change in my pockets and no single dollar bill I will sometimes cough up in such situations.

Sensei continued on with his story.

“In that pause, I looked at my lone twenty dollar bill and felt a tug—head versus heart–wanting to be generous yet conscious of myself weighing if maybe twenty dollars was being a trifle too generous.”

This is what I love about our teacher. He readily admits to being fully human, to making mistakes, to losing his temper, to wondering about the limits of generosity and sharing with us that even he—a very learned, compassionate man– pauses in such moments.

“But then, before I could pull back the words, I said, ‘Jason, this twenty dollar bill in my wallet seems to have your name on it.’ And I handed him the money. The tug, the head-hear- thing, disappeared instantly.  I was at peace.  It was, of course, the exact right thing to do. I went on with my day.”

I sometimes wonder what must be the state of life for someone to turn to the streets, hands always extended, asking all day long for help.

Photo credit: Flickr

I have heard what might very well be tall tales of people having their ‘begging clothes’ stored in lockers at Port Authority bus station, folks who come into the city daily, don their costume and make a good enough living to have a nice home in a less expensive borough.

Even though this legend may be true in rare instances, does it matter? It feels too convenient for me to simply add this ingredient to my recipe of reasons to rush by those less fortunate than I. I wonder if perhaps their ruse serves to remind us of the enormous financial and social discrepancies here in America, the tragically deep chasm separating the haves and the have-nots.

Is it my business if the person I give money to decides to buy drugs or alcohol? I think not. I have a life that keeps me fairly cushioned from the kind of sadness and despair that a drink might help create a moment of relief from. Who am I to say whether my money pays for food, a drink or provides a nice home in some distant corner of Brooklyn?

My business—at the zendo and in life– is developing compassion and generosity. Let the others deal with their own karma. And, in a way, aren’t we all holding out our hands, asking for something?  If not for money, then perhaps love, a child, a new house, a vacation, a promotion, a visit, a God, a cure, a few more years?

I will probably continue to feel a tightness in my encounters with the homeless.

I hope in those moments I recall the lovely lightness I have also experienced when the money leaves my hand and makes its way out into the world in ways I will never know about nor care about, my wish for the recipient only “Be well.”


The views and opinions expressed in this article are those of the author(s) and do not necessarily reflect those of BK Reader.

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Michael Milton

Michael Milton worked as an Associate Producer with Marty Richards, Sam Crothers and Robert Fryer at The Producer Circle Co. in New York City for over twenty years. Broadway: THE LIFE (2 Tony Awards),...

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