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.

Out of The Mouth of Babes

Humility is something we become well-acquainted with at midlife. Maybe it’s the first sign of wrinkling around our eyes, or the realization that we don’t move as fast on the tennis courts anymore. Or maybe the humbling happens the day we get our first AARP invitation in the mail.

The triggers are different for each of us, but there comes a time when we realize we are aging. Time is shrinking and we notice.

This can be a humbling time for many of us. But as the Tao Te Ching teaches, humility is a grace. When we see ourselves through new eyes and release old stories, even old ideas of who we once were, we paradoxically become wiser. That’s because we become teachable.

And at midlife, being teachable is an elixir. It’s the fountain of youth, the green juice that will keep you forever young and healthy.

So what do I mean by teachable?  I mean stretching your mind,  shuttering your ego and allowing people–particularly young people–to teach you new things.

For instance, I am fortunate to work around several spirited twenty-something year-olds who grew up in the can-do millenium, who speak technology like it’s their native tongue. Not so much for me.  I admit I’m a dinosaur when it comes to anything more than the basics of technology. And yet here I am, at midlife, setting up a wordpress website and teaching myself some of the basics of this technology so I can communicate my thoughts and share my work with the world.  My young friends have served as my guides and teachers here.


And twitter? Thanks to my young friend Natalie, I now know the value of a hashtag, and I understand the basics of this medium. I’m also able to recognize its beauty and potential to serve as a gateway to new information–each thread of discovery unravels another thread and another in an endless stream of knowledge. It’s exciting and humbling for me to think about how connected we all are, and what I might uncover.

And if I wasn’t willing to humble myself and ask someone nearly half my age to sit and be patient with me, my eyes wouldn’t have been opened to new teachers, new information, new technology.

So I say, become a student at midlife. Be humble and be willing to learn new things. Are there areas in your life where you can step out of your comfort zone, stretch a little, discover something new? Are you willing to become a student of life, to admit you don’t know? Are you willing to raise your hand and say to someone, or to the universe, Teach Me?

Be teachable and weave threads of new knowledge into your life. See what humility can create in your life.