I used to be somewhat skeptical of anyone who ever asked me for money, yet when I met what would be my future husband, I was taken by how he would give, without reservation, to anyone who simply asked for the help. Lucky for me, I married him.
We often drive by people in need on the street as they hold their sign, possibly passing by as if it is not our problem. But that person counts and exists just as we do on this planet, and as a child, I imagine that person probably never aspired to one day be standing on a street corner asking for a handout. It is easy to make judgements, but I think it takes great courage to ask for help. If they are there asking, they probably need it more than you.
Several years ago, while volunteering on a project to give bags of goods to homeless people, we were encouraged to speak with the people to whom we were giving. What an eye-opener to hear how some people had gotten to where they were and why. While some that we met clearly had signs of mental illness, many were quite astute. I remember thinking at that moment, how fragile life can be and that anyone could be in those shoes.
Each one of us has probably worked hard for our money, and none of us are required or obligated to give, but if only we were all so fortunate to have something in our pocket to give (big or small). I, for one, am grateful to be the giver in this scenario rather than the receiver.