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Giving to the Homeless

Recently, I’ve read a number of posts that discussed whether or not one should give to people on the street with their hands out. I have my own thoughts to share on this.

On a business trip to Chicago, in the late 80’s, I passed by a number of homeless people, each time I’d pull out a dollar and hand it to them. The guy I was with asked me how I could hand a dollar to every homeless person I passed. I looked him in the eye and said that to me it was remarkable that he could walk past so many homeless and not reach into his pocket even once.

Years after that, I heard this story. There are two men of the cloth (pick a religion) and as they pass a homeless man, one of them hands him a dollar. The second man says, “I donate to organized charities, I won’t give the street beggars money for fear that one on them will buy alcohol or drugs with it.” The first man responds, “I understand your position, but you see, I give a dollar to every man with his hand out in the hopes that one of them will spend it on food.”


For me, part of giving to the person on the street is certainly for the good feeling it gives me. Donating to an organized charity is great, and I do that in a fair amount, but it’s also a good feeling to not walk by someone asking for a handout.  In the big picture, handing over a dollar or two isn’t going to hurt me, and sets an example for my 11 year old. We have an annual New York City visit coming up and she’s already told me she plans to use her allowance from the last few weeks so we can take turns helping out.

What is the image above? A platter that my wife got me last year. When I lived in the city (I left NYC 25 years ago, but if I can steal a delivery style from Kanye West “New York is the greatest city of all time.”) one of the things I loved the most was Broadway. Even as a young man I was always impressed by the juxtaposition of the theaters, then selling $100 tickets, and the people on the street with their hands out as soon as you stepped outside. These are the singles I accumulated over the past couple months, so I don’t have to make change for the city. I hope to bring back a story or two from our trip.


  • JOE December 22, 2009, 4:34 pm

    Hey Jason, thanks for visiting. Yours was one of the posts that inspired me to write one of my own.

  • Jason @ RedeemingRiches December 22, 2009, 4:01 pm

    I love this topic! This is one that I often think about even though I live and work in a suburban area and have very little interaction with homeless. I really believe we have to have a heart of humility when we approach these situations.

    It’s easy to look down on them or judge them, but that shouldn’t be the case.

    I did a post on this a while back called Should You Give Money to a Homeless Person and I had a few comments come in that talked about giving McDonald’s or some other restaurant gift cards instead of cash just in case they’d buy alcohol etc. I thought that was a great idea!

    Bottom line though is that seeing them as a person with a soul and a story goes a long way to aid us in our humility as we help them.

  • Evolution Of Wealth December 23, 2009, 12:06 am

    I think you have a great perspective on this. I think a lot of people lose that. I don’t see a lot of homeless people where I am but I do always try to give to the bell. You all know what I mean, the ringing bell outside the grocery store. I saw an interesting post on this a few weeks ago, We All Need a Bell.

    Happy Holidays!

  • JOE December 23, 2009, 12:25 am

    Thank you for visiting and for the kind words. Happy Holidays to you as well.

  • JOE December 23, 2009, 12:53 pm

    It varies depending on time of year and street, but I’m sure we’ll meet quite a few. Weather should at least be in 30s-40s, not the single digits like just before New Year a year back.

  • Jackie December 23, 2009, 12:00 pm

    I like the idea of bringing singles ahead of time and planning to give to the homeless. I rarely do, but not because I don’t want them to potentially do something “inappropriate” with the money. I just pretty much never have cash on me. I have given food I had with me on my way home though, and I still need to give out the money I’ve been carrying around for a few weeks now for that purpose.

    As a side note, I was just in NYC and didn’t see many homeless except in the subways and train stations. Maybe it was the snow.

  • JOE December 23, 2009, 9:04 pm

    No rocks, my friend. I hope the story of the two men of the cloth illustrated this is not a simple debate. There is no right or wrong. The amount we give to organized Schedule A charities is just shy of $10K/yr. Over the course of a year, fewer than 100 singles given to individuals. I admit that it’s as much about me as it is them. I feel better not walking by a fellow human being with his hand out.
    Happy Holidays to you and yours.

  • Len Penzo December 23, 2009, 8:26 pm

    I do contribute freely to every street corner musician I see and, like EoW, the bell ringers too. Oh, and the girl scouts. But I never give money to beggars on the street corner. Ever. I do buy them lunch or dinner when I think they really are down on their luck.

    That being said…

    I’m sorry, but I just do not see how giving the average beggar a handout as being helpful in any meaningful way. Call me a heartless SOB, but it is my opinion that giving beggars money is actually doing them – and society as a whole – a big disservice.

    Instead, I think that money would be better spent going to the local homeless shelter.

    “You ARE a heartless SOB, Len.”

    If you say so. But to me, there is no need for anybody capable of standing on some street corner on their own two feet to beg for money with a cup in their hand – my God, this is the United States of America, the greatest country on earth. The land of opportunity. Have a little self-respect. Despite the tough economy, there are entry level jobs everywhere. This ain’t Bangladesh.

    Get a frappin’ job, even if it is at the local hot dog stand. “But, Len, you can’t live in NYC on minimum wage.”

    Well, then move to some place where the cost of living is cheaper.

    If you have to, hitchhike.

    I’ve got my shield up. Let the rock throwing begin…

    Len Penzo dot Com

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