How A Homeless Woman Taught Me Humility

blog pic1-1Walk through most any major city and you’ll inevitably find homeless people propped up against building walls or huddled near church fronts. In my own city, I see people standing on the side of the road begging for money, some holding signs, some standing stoically, some standing dazed. Some pace between cars, agitated it seems, by the noise, the traffic, or maybe it’s just the sheer frustration of their plight.

When I see homeless people standing at traffic lights I do what I imagine most people do. I start squirming. Then the questions begin. Should I stop and give the person money? Should I avert my eyes and pretend I don’t notice him?

Why is he standing on the  side of the road? Where is his family? What got him to this place, this street corner, this intersection of hopelessness and despair?

Why isn’t he working? Is he healthy? He looks healthy.  What wrong turns or unhappy endings have led this person to this particular corner in life?

Sometimes I  even wonder what the person might do with the money I give them.

These questions speed race through my mind, and then I usually roll down my window and donate a dollar or two. I know a lot of people think it’s a bad idea to encourage people to beg on the side of the road. I’ve been told I am likely feeding their drug habit, or a gambling vice or worse.

The truth is, maybe I’m feeding my own vice. Maybe I’m the one looking for a little redemption. Maybe I’m offering up a few dollars, the way I’d offer it up in church, as a donation, as  a thank you prayer. There, but for the grace of God, go I.

I know a dollar or two won’t change my world. But if it helps someone buy a burger or to secure a bus ticket or lodging, I want to help. If that person is manipulating me and the system–so be it. Because I still have to wonder how they got to that point in life…where standing on the side of the road begging for money seemed like a better idea than being part of society.

I do my best not to judge.

Last week I was in New York City. My first morning there I got up early and took a walk. Just steps from my hotel near a shop with Statue of Liberty trinkets and I Love New York t-shirts, sat a young homeless man. He looked to be around the age of my son, and he sat in the middle of the side walk with defiance in his eyes….and with his jar of change and not much of anything else.

People walked hurriedly past him. I stopped and leaned over and dropped a dollar in to his cup. He barely noticed.

But I felt happy. Further up the block, I saw a disheveled, wild-eyed African American woman on the corner. She wore sweat pants and had cornrows that pointed in all directions and her feet were sprawled across a grate. I passed her by because she scared me a little.

But then I turned around and went back. I noticed she didn’t have a cup in front of her so I leaned in with my dollar bill and politely asked, “May I give this to you? She looked up at me with angry eyes and hissed, “I don’t want your money!” And as I took a step closer, she growled louder, “Don’t touch me!”

I moved away, stung, hurt and humiliated, and angry all at the same time. I was angry with myself because I realized that my well-meaning attempt to help had backfired and had only humiliated her. Our interaction made me see how easy it is to become arrogant in our giving, in thinking how our tips to homeless people help THEM more than they help US.

The truth is, I like to help people because it makes me feel good to help others. And it reminds me of how blessed I am.  But I’m not sitting alone on a street corner watching strangers hurry by to a better life like the woman who passed on my aid. How arrogant she probably saw me to be….

She only reminded me of the truth– minutes after I gave her money to brighten both of our days,  I would be enjoying a nice big breakfast in the hotel restaurant  down the street. And she, that woman of the wild eyes, would still be sitting out on the street and how dare I  forget her face, or feel better about my life, for the smallest of donations. It was not a fair exchange and she knew it.

I carried the shame of that exchange for days.

On my last day in Manhatten, I treated myself to a beautiful dress I purchased at Lord & Taylor. I had saved some birthday money and I wanted to buy something special for myself to remember my trip.

As I walked down the avenue I passed an old man with cloudy blue eyes and dirty clothes sitting against a building with a small cup of change. The street was crowded, I was carrying a bag and it was easier to keep walking.

I did, for about a block, before turning around and walking back in his direction. And as I pushed a dollar bill into his plastic cup I looked into his eyes, smiled and silently said, “Thank you.”

He nodded and smiled. I walked away, feeling humble, and not so good about myself. How could I? It was cold and I was carrying a beautiful new red dress in my tony Lord & Taylor bag, and no amount of spare cash was going to square things.

And I knew it. On this day, all I could do was count my blessings as I headed back to my hotel and remember the gift—the grace of humility—that I’d carry with me for a long, long time to come.

If you’re interested in more thoughts on integrity, compassion and grace, particularly at midlife, read my book Tao Flashes. Or visit me at or on twitter @taoflashes.


10 thoughts on “How A Homeless Woman Taught Me Humility

  1. Nice thoughts Lisa, on a topic few seem to think about. We saw a homeless man on the highway in Pueblo and Mike gave him a dollar, as he always does. Then he said to me, “I just felt sorry for him” and I said, “Like you did for me when you met me?” We both laughed!

  2. Working in Manhattan for 6 years I used to step over people – STEP OVER – without even a thought or a glance. Because I had gotten used to seeing them. Can you imagine what it takes to not even notice them? I am ashamed of myself now, but in my hurry to get to work, this twenty-something hardly gave them a thought.

    If they carry signs about being a veteran or have animals nestled next to them, my heart bleeds and I give. Last week I didn’t give to a “vet” and that thought still haunts me.

    I know we can’t change the world, but my heart aches for all of the people forced into this kind of life.

    • Cathy, I really appreciate your heartfelt comment. It is a courageous thing to look at all sides and not white wash things. We have all passed by people in similar situations and I think part of the human experience is learning how to keeps our hearts open. We learn and we grow and we do what we can….especially when life finds a way to crack our hearts open. In my experience, this kind of growth is ongoing……at least it is for me.

  3. It breaks my heart as well as I see more and more of them in our little suburb. Last week I saw the police making a woman leave an intersection. They try to push them back to the ‘big city’.and it made me sick. Why couldn’t he have taken her to a shelter somewhere to get some help instead of standing there coldly telling her to leave. I gave her $10 anyway and got a nasty look from the police officer but I didn’t really care what he thought about it. She could at least get something to eat. That is my biggest fear, there are so many homeless people out there. How did they get there and what will stop me from ever ending up in that situation. It’s a very scary thought.

  4. Lisa, You are so kind. And you were only trying to help that woman…don’t be hard on yourself. It’s interesting to see how our perceptions are not always reality. But know that you did make the other people who accepted your kindness very happy.

  5. Sheryl, you’re so sweet to make me feel better. The experience really did shift my perception….and made me take a step back and look at things differently. I still carry that experience and think there’s a reason. Live and learn….

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