My wife has commented through the years that I am an easy mark. The word gullible has followed me around in both my personal and professional life. I often attract requests for change, requests for a few minutes to talk about a really great offer, and even rides across town. When I commuted to Manhattan each week for school, I would carry extra peanut butter sandwiches and granola bars. Needless to say, some of my regulars stopped asking for money.

The subject of “charity” or “giving” is rather touchy. Words like “deserving” and “undeserving” quickly roll into an “us versus them”. Then its a short trip into politics, where I refuse to go. I was raised to understand that I could very well find myself in a situation where I need help. What if I were in need? What if I had lost everything and needed a simple handout or very simply, a kind word? These questions persist, as I watch a twenty-something-year old man knock on yet another car door at my local CVS. I already gave him a dollar.

I flash back twenty years ago when I found myself lost in New York state as I travelled home from a family wedding. I made the decision to leave the wedding early, drive back to Connecticut for work the next morning. As a member of the wedding party, I left a bag with my sneakers at my grandmother’s house and spent most of my money on last-minute-wedding-related items. Barefoot, I drove home missing the exit for Connecticut. I was limited to my VISA card, should I need money and there were no cell phones in those days. Not smart and not well-prepared.

I stopped at a small gas station with broken lights, to ask for directions. I debated wearing the hot pink heels from the wedding with my running shorts, but decided to walk into the store barefoot, something I had never done. In that moment, I catalogued a variety of risks, including safety. In that moment, I had no cash and I was lost. If my VISA card did not work or wasn’t accepted, I was in serious trouble. There were no cell phones and I had used my change for tolls. In that moment, if I asked someone for change, what would they have thought. Am I being scammed? What will this person do with the money? Am I a fool for giving my money to someone able to provide for themselves?

At the end of the day, I couldn’t begin to imagine what brought this individual to this place in their life. Are they simply having a bad night, like the one I had over two decades ago or if is a lifelong struggle? In many ways, I’m not equipped to make this decision and I don’t want to. Rather, I ask myself two questions: do I have a dollar to give, and it’s almost always…yes. And, what if this were my child? The answer to these questions are a lot easier and as a result, so is my decision to give.