I am often approached by people and organizations asking for money. Sometimes as I walk down the street, sometimes in my mailbox, and sometimes by the Ronald McDonald jar next to the cash register. I often wonder whether I want to give or not, and how I would feel afterwards in various situations.
So, for the month of March, I decided to try giving whenever I was asked, to experience it first hand. Every time a bum on the street asked for a handout, I gave something. Every time I went to the store and there was a jar by the register, I gave something. Every time I got a piece of mail from a random charity, I mailed a check. I even responded to emails asking for money (e.g. from political groups).
Before I started, I thought maybe this would be a real eye-opener, and I'd want to either give a lot more going forward, or give none at all. In fact, it didn't turn out to be so clear. My experiences were roughly case-by-case. Indeed, sometimes I was surprised at the joy of giving. I would get very sincere thank-yous, or do a lot of research about who/what I was giving to and come away with a real feeling of having made a good decision. Other times, I was unexcited about giving to the person who was asking based on judgments of my own, and indeed after giving I felt roughly nothing. But, a few times I was surprised as my prejudice had clearly been wrong---I went in thinking this is not the right thing to do, I'm only doing it because I agreed with myself that I would but came out feeling good about the giving. This was the exception rather than the rule, most of the time I didn't learn much.
One other thing I learned is that giving feels the best when it's personal. Either I'm face to face with the person and talk about it to get a good understanding of the need, or I do my own research and come to my own conclusions that this is a good spot to spend some of my efforts.
Now that the month is over, I will go back to a case-by-case consideration, though I suspect I will generally be more generous now that I've done this---especially in cases that are not familiar.
And a random link on the subject: giving anonymously online.