How a slice of pepperoni pizza and a large coke changed it all

A few years ago I decided that I would make every attempt to give whenever someone asked for change on the street. At the time, it seemed radical and maybe a little foolish. But it has been one of the best decisions I’ve made in recent years and has really shaped my personal philosophy on money and philanthropy.

The first time I responded to someone’s request was one December night eight years ago. I took a friend for a snack downtown as our friends secretly prepared a surprise birthday party for her. As we walked down the main street, a middle aged man standing with hands crossed in front through frayed gloves, politely and eloquently asked whether I had some change to spare.

I prepared to shake my head, look away, and silently pass by with kindergarten-trained instincts not to talk to strangers. But she stopped. So, I stopped. And she gently asked “It’s Victor, right? I’ve seen you around.” Feeling a little guilty for waiting to just pass by, I fished out all the change I had in my pocket. Full of trepidation, I nervously watched the conversation continue. “Who is this person? How does she know him? What did she have in mind?”

She met him through some volunteer work with the homeless. Towards the end of the conversation, with warmth like talking to an old friend, she asked what he needed then if she could buy him some dinner. A slice of pepperoni pizza and a large coke. We brought him two slices and an extra large.

Shortly after that experience I started a habit of keeping a folded one dollar bill in the front fold of my wallet, precisely for occasions like this. Those one dollar bills led me to fascinating conversations with strangers including trading recipes with a former chef, hearing about different wars from veterans, talking to a former psychologist, diffusing arguments with people suffering from dementia, hearing women escape from abusive relationships, and much more. I’ve learned that circumstances can lead anyone (including me) to similar positions, so why not be generous when one can?

One dollar turned into five dollars, because what can anyone buy with one dollar anymore? And now, I dedicate $50 a month just for unplanned generosity including cash, meals, and other needs. I have and continue to learn so much about the needs of the poor, how charity leaps off your checkbook to the very street you live on, and how transforming even small gifts can be.

"What If" Charge: What if the next time someone asked you for change to spare, you asked for what? What if you give that person a dollar or treated them to a slice of pizza and a large coke?