I was asked this question by one of my clients recently.  I still recount this story daily, every time I drive by where it happened.

I was inspired and moved by an experience that took only about 20 seconds.  It was a Friday, it was pouring rain and a bit cooler outside.  I had fought traffic on the way home and getting a bit frustrated, I was worn out from a long week and was just ready to get home.  My wife and I were debating whether to cook and stay in with a glass of wine or go out to eat at a cool new place downtown.  I was leaning for staying in because of the weather, sounded pretty stellar to me.  About that time I was thinking this to myself a driver cut me off.  I was just exiting the highway and coming up to a stop light.  Once I was stopped I noticed a man sitting on a milk crate to my left, rain pouring down on him, crying his eyes out.

No other way to put it, he was just sobbing. For a split second I didn’t know what to do. Quickly I offered him a zip lock bag full of items that my wife I keep in the car. (we learned this at an NCF Passion Awards a few years back).  But my little offering seemed so little I almost didn’t offer it.

I wanted to do more.  I offered it to him and he gladly accepted.  I headed home, sobbing all the way.  My wife and I talked about that encounter for hours.  I still wish I had done more but loved that at the very least I was prepared to give something.  It’s changed me, I look for him all the time.  I think about him all the time. I prepare for giving more than I ever before.  Instead of turning away when we see a homeless person we both find ourselves actively looking for them, because we are prepared.  It’s small but we’re still armed and ready.  It’s a whole new way of looking at generosity….preparing for it.