What is the best way to provide care to a stranger? Anna Chistyakova explores available options and possibilities to help a homeless person and finds herself overwhelmed, yet is not convinced what she should be doing as a giver.

Almost every day on my way to work I see a man with grey curly hair dressed in a white wrinkled shirt and red tweed pants. He always smiles and wishes me a good day. He also sells the “Big Issue” and I guess he is homeless.

As I have been passing by him every now and again, I started to wonder what would be the best thing I can do to help. My experience of philanthropy and charitable giving is limited to providing professional services pro bono, and donating blood, where I was part of the team. In this case, however, there is only me and the person in need, which makes it much more personal.

The easiest way to help him would be to buy a magazine. “Big issue” had a good idea of training people, and making the whole experience about earning rather than begging. I liked their motive to tackle social problems via business. But I am not sure if their business model actually still works.

If the Big Issue Foundation wanted to make people like me buy a magazine, I would assume they would make more of effort to differentiate their content from the content of those street newspapers that one can get for free. Why would I want to pay for a magazine that has nothing particularly interesting for me to read about? Moreover, all the Big Issue vendors do not themselves seem excited about their product, which does not inspire me either. So I didn’t like this option.

I could just give him money without taking the newspaper. But campaigns like “Killing with kindness” invite me to think about giving money to an individual as rather a negative thing to do. They suggest I donate to a homelessness charity instead, to ensure that this money is spent on long-term benefit for these people and not on drugs and alcohol.

I immediately imagined passing by this man saying, “I care about you and want to help. That is why I’ll give this £5 to a homeless charity instead, because they know better what to do with it and will guarantee you don’t spend it on something stupid”.  Apart from the likely abuse I would receive for being so patronising it also certainly will be of no help to the homeless man at all.

Who am I to judge their choices in life and treat them by my or charity’s standards instead of theirs? Wouldn’t it be more caring of me to give him the £5 and make him happier, even if he spends on alcohol? After all he has no admin costs, no fundraising costs and every penny goes direct to the beneficiary. Donating to a homelessness charity doesn’t feel great as an option.

Yet I also hesitated to just give money. I knew it would buy me this warm feeling about myself being a caring person. But then what would I feel passing by him next week or month and not giving more money? And would my £5 actually make his life better? In general, giving money this way is an easy win but a slightly selfish thing to do but I was hoping for this giving act to be more effective and even sustainable.

Not satisfied with the options available immediately I started thinking about what it means to truly care about someone. The first thing that came to mind was doing something nice for them without wanting or asking for something back, namely being altruistic.

Altruism, however, does not have to come up naturally. I’d even argue that giving without expectations to get something in return requires some preparation. For instance, I try to think of what my friends like when choosing a birthday present for them. A cheque for £30 is not as good as a book they were looking for, even if it costs £12. It doesn’t even have to be material. Good quality time together with my friends brings much more joy for me than a Selfridges’ gift certificate.

When we make an effort to match our gift with what someone would really enjoy, than it gets personal, becomes a sign of our care and esteem. It works with our friends and family as well as with people we have just met. And when we get it right, I can bet a good deal they would not think, “Oh, gosh, I wish I’d gotten the money”. So instead of offering a fiver or some old clothes to the man in the red tweed pants, perhaps I could give him something that will make him happier. But what could that be?

I spent more time thinking of what I can or should do and felt overwhelmed by options, yet none of them seemed perfect. In the meanwhile that man was still standing there, waiting for people like me to make up their minds. Passing by him this morning again, I thought that maybe it’s not about choosing a perfect option, but about taking an action. So I stopped, said “Hi”, and started the conversation. 

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We asked our newsletter readers to tell us who would they most likely to give their spare cash to. Thank you everyone who voted! Here are the poll results.

If I had some spare change I would most likely give it to a person who:

How would you answer?