Should we give till it hurts? No, I don’t think so. We want less hurting in the world, not more – that’s the whole idea. But part of me wants to ask: if it doesn’t hurt, how do I know I am doing it right?

An article in this week’s Chronicle of Philanthropy profiles a mathematics professor at Northern Virginia Community College who works two additional jobs so he can earn enough money to give away half of his $100,000 income each year. He can barely afford his taxes and mortgage. Watching the accompanying video, entitled “Giving Until it Hurts”, really got me thinking.

I am so fortunate to be able to give what I consider a meaningful amount without sacrificing my own financial well-being. But what if that weren’t the case? Could I still “afford” to be generous? Would I be? If I just give away what I have that’s “extra”, what does that say about my generosity? Could I give more this year? Today?

Some of the most generous people I know have nothing to spare but they give anyway. I have seen patients stuff a bill or two in the donation jar at the free clinic when I know they just lost their job. One grateful patient says he always thinks of us first whenever he earns a little money, and regularly sends us checks for $50. He lives in a rundown house on next to nothing and is one of our major donors. I don’t think it hurts. I think he feels great about it.

Maybe by saying “give till it hurts” we really mean “give till you feel it”. That’s a lot of what my Month of Hundreds is about: paying more attention to who and what is going on around me; being more present and more conscious. Starting Friday I’ll be giving away $100 a day!