This past Friday I hopped on the train with a bag full of Homeless Helper Bags to distribute before meeting a friend for lunch.

If you’re not familiar with my annual preparation and distribution of Homeless Helper Bags, please read this post before continuing. I’ll wait.

Back? Great. Read on . . .

Once again, I’d collected supplies all year and made a peanut butter and strawberry preserves sandwich (bread was on sale at Jewel for 99 cents a loaf!) for each bag. I had prepared 12 bags thinking they would last me most of the day. My plan was to pass out bags to the first 12 people I saw and to attempt to engage in a short conversation with each of them because I believe that genuine interaction another person is at least as vital as a few toiletries and sandwich.

I was barely outside of Ogilvie Transportation Center on Madison before I saw a homeless woman with two small children. They were leaned up against a building, sitting on the ground and my heart broke for the first time that day. The woman had a sign asking for help, not money, just help. Naturally, I gave them three bags and had a short conversation with the mom. Looking into her eyes and those of her children, I worried about where they’d spend the night. Although it was about 68 degrees and sunny at that moment, I knew that by early afternoon, the rains would come and by early evening, the temperatures would drop into the 40s, if not lower.

Crossing the Lyric Opera Bridge, I saw a discarded Homeless Helper Bag (not one of mine) on the ground and suddenly wondered if my efforts were a generous gift of help or a way to assuage my own feelings of unearned privilege. Do the bags I so carefully curate to insure parity and usefulness actually make a difference to the recipients or do they just make me feel good?

I continued walking towards State Street on Madison stopping each time I saw a homeless person to give them a bag and chat about the contents (toiletries, socks, gloves, a sandwich, and snacks), my hope that the bags provided them some relief, and my wish that things would turn around for them. Each person I spoke with was grateful for lunch and appreciative for a moment of non-judgmental conversation. Some even looked at the bags in awe, seemingly surprised that someone took the time to think of them and their needs rather than just tossing coins at them, but not really seeing them.

Of the 12 homeless people I spoke with and gave Homeless Helper Bags to, there was one woman and her two children under 5 years old and nine men. They represented all races; two or three were in wheelchairs; one sold Streetwise; and although most appeared to be in their 50s or 60s, the mom appeared to be in her 30s and one other man appeared to be in his early 20s.

My 12 bags were gone in less than 30 minutes and I only made it to LaSalle Street – a total of five blocks. I could have easily brought another two or three dozen bags. I will next time.

After handing out my last bag, I found myself standing in front of St. Peter’s Catholic Church so I walked in to sit, meditate, and journal about my experience passing out Homeless Helper Bags. I prayed for the homeless people I’d met, that they’d find a warm place to sleep that night, remained safe, and got the help they needed to get off the streets. As I journaled, I saw each of the faces of the men and women I’d met that morning and suddenly remembered the adage about acts of kindness not changing the world, but changing one person’s world. If I accomplished nothing else, I hope that the people I met that morning went to sleep that night knowing that one person genuinely cares about them because I really do.

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