When I first moved to Chicago, I worked in the suburbs but I spent many weekends walking around downtown Chicago and the near North and South sides. I eventually got over my small-town tendency to say hello to, or at least nod at, pretty much everyone I passed on the sidewalk.
I also quickly realized that if I gave loose change or a few dollars to every person who asked, I would in short order not have much money of my own. But that reality was in direct conflict with my desire to help and the intense discomfort I felt simply passing by someone asking for my help. So I decided to concentrate on those who said they were hungry, asking either for food or for money to buy food. I would buy them food, I thought.
And so I did. Over the three years before we moved to New York, I bought dozens of sandwiches, hamburgers, cups of soup and more. Some were purchased and given to people, others were shared with the person over lunch, or dinner, or breakfast. It was these latter encounters I enjoyed the most. I met some wonderful people with some touching stories who seemed truly thankful I had spent time with them. Very often they asked for nothing more after we ate. Perhaps it's my naiveté showing through, but I felt like over a meal and conversation we could have been any two people just eating and talking.
On a completely selfish level, I was as thankful for these moments as the people seemed to be. I was grateful for the gifts of time and money that I was able to share with others. Nevertheless, I wasn't able to overcome the feeling that whatever I was doing wasn't in the same vicinity as "enough." The hunger, the poverty, the addiction, the mental illness – whatever it was that put those people on the street – existed long after I said goodbye. Back then, though, that didn't stop me.
Then we moved to New York where I had a new job and, suddenly, less free time to spend walking around. Less time to help. That's what I told myself, anyway. There were also a lot more people looking for help. But it was different there. It was less direct. Whereas here someone might come up to me, look in my eyes and ask for help, in New York I saw more people sitting to the side with signs and cups. I'm ashamed to say it, but it was just easier to walk on by. And that, rather than helping, became my habit.
I brought that habit back to Chicago with me in 2003 and with a few exceptions here and there I have maintained it. Now I work downtown and the crowds are no longer exciting and fun, as they were when I first moved here. Now they are an annoyance to be navigated as quickly as possible on the route from my office to the train or wherever I'm going. Now I'm much more likely to buy a StreetWise from Doug, the vendor at Clinton and Jackson streets, on Friday mornings on my way to breakfast. There have been a couple of times when I thought I should invite Doug to breakfast. But then I worried that time spent eating with me would be time he wasn't selling. I'm over-thinking it.
And my attitude has changed. I've become more skeptical, I have more of an edge now. I find myself succumbing more quickly to the notion that what I'm doing isn't enough, so why do anything? That is a horrible attitude and I am trying to shake it.
So this Thanksgiving, I give thanks for the memories of the days when I more freely invited people and possibility into my life; when I felt more helpful – naively or not; when I had an honest hope that little gestures could make a difference. My goal by this time next year is to have gotten back to that. In the meantime, I give thanks for what I have – family, friends, health. I wish the same for you, this holiday season and always.