"I’ll Pay You Back..."

Chicago, Lower Columbus Avenue November 22, 2018

Chicago, Lower Columbus Avenue November 22, 2018

Part 2 for those who read my last blog. But it’s also fine to start here.

So my niece went crazy in the Dollar Store and TJ Maxx.

The project was to get things for wellness packages to distribute to homeless people over Thanksgiving weekend. 

She had done some research on what those living in the streets need most and it was socks and, believe it or not, foot fungus cream.  Anyone would feel better in the socks she got.

 She understands the world through asking Google and I love her for that. 

The night before hitting the streets we laid out the loot on the living room floor. It was a lot. Warm, big comfy socks, foot cream, tissues, granola bars, Dunkin Donuts certificates and more. We made bag-filling stations where everyone got to put an item or two into zip lock freezer bags. Her seven and eight year-old daughters loved the task. They would hold things up like Annie’s Gummy Fruits, a treat they enjoy themselves, and exclaim: "They'll like these." 

With the wellness kits in hand we opted for public transit to downtown Chicago. The family was on mission.

Family with a Mission, Oak Park, IL Photo: D. Wilson

Family with a Mission, Oak Park, IL Photo: D. Wilson

There is nothing like trying to break the barrier. By that I mean, the barrier that crops up between us and the homeless. We adults look thru them so easily, saying "no, sorry."

Stella and Vivienne felt so good about this. It was like teaching them they could make a difference.

Well, that was the intent. 

We got off the train at State and Lake in the heart of Chicago’s busy Loop. It’s on a path where I’m regularly approached by needy people. 

The girls were joyous to find people sitting in the sidewalks who obviously needed help. Putting heads together, with the help of a comment from a friend, we had scripted our introduction and taught the girls to say it so they would feel comfortable. Not that they were uncomfortable in any way helping people but we wanted to chose the most respectful language:  

"My name is Stella and I wondered if you would like a wellness kit." 

One by one, we looked at people in their eyes and handed them a kit. I missed one guy who was on the left side of the sidewalk and we were focused on people sitting near the buildings on the right. I looked back and saw him. I went back, he was suspicious and then touched. One woman near Macy's on the sidewalk declined Vivienne's outreach and I didn't understand. I talked with her and she said: “No thank you.”

I wanted to make certain we got to people who weren't as brave and well-bodied as those who were on busy State Street. We had heard from a hot dog vendor that there was a village of tents under Columbus Drive near the commuter train station. 

Off we went deeper and deeper into the bowels of the city. I asked myself where I was taking my sweet family from Michigan. Yet I had also asked them if they wanted to keep going and they said yes. We grabbed the little hands of the girls and trekked on. We didn’t find a tent city, only well-swept streets. Spotless, not even one piece of litter.

We found very few homeless people there and I still wonder where the rest of them are. 

Family with a Mission, Oak Park, IL Photo: D. Wilson

Family with a Mission, Oak Park, IL Photo: D. Wilson

Back to State Street with about 20 kits left, big bags, and two little girls. While the world is chasing bargains, we are wondering if we’ll find enough people to give our goods to before a Christmas play we planned. I knew we couldn’t take these big bags into the Chicago Theater. I also wondered if I was a strange Aunt to visit and hoped they were enjoying our project as much as I was.

We found our people in need though, seeded thru the Black Friday crowds on State Street. We finished our mission which felt good. Although I know this doesn’t solve the problems of their living situation. Small steps.

Most people think because someone is homeless that they’re alcoholics, drug users or scheming lazy people. I don't believe this is true. Some friends said: “don't give them money they'll use it on alcohol or drugs.” I wonder if that thinking doesn't just protect us from the unthinkable. 

Maybe some of the homeless are people like all of us but who’ve had more than their share of bad breaks and couldn’t cope. I say to the doubters and skeptics: being homeless would be very hard. If I am ever homeless, bring alcohol and drugs. Others talk about the "homeless mentally ill." Maybe it's people who are sick and can't manage their lives. Or, maybe if someone loses their home they become ill. I don't see how anyone living on a sidewalk could have good sleep, basic nutrition, love or any of the other essentials we need to be whole, healthy and happy. 

No one wants to be homeless, and being homeless doesn’t mean one has no dignity. One woman we approached was graciously touched by the girls’ giving but looked at me, smiled and said: “I’ll pay you back.” I said, “No, it’s our pleasure; we want to help.” She smiled and said firmly, “I will pay you back.”

She repeated it again as I nodded and stepped back into the crowd.

It was moving. I thought I was going to cry. Everyone deserves to feel a sense of dignity. I know that today even better than I did a week ago.

By the end of the day, the girls felt good about their Thanksgiving outreach and we were all exhausted from our holiday’s events.


It’s the season of helping. I am sharing the girls’ story to help you think about it. Kids do help save us in spirit.

Consider how you see homeless people. Challenge the natural desire to hide from what is awful that we believe cannot change. It is good to find a way to jump in versus having to shut ourselves down emotionally.

There are many ways for all of us to help the homeless in Chicago, and I hope you will consider those with me. You will be a beneficiary of any kindness you give.

1) Housing Forward helps homeless people on the west side of Chicago and the near west suburbs. Volunteer at one of their overnight shelters or contact them here: https://www.housingforward.org/get-involved

2) Help out at your local food pantry. The one closest to me is: https://www.oprffoodpantry.org/

3) Volunteer or donate to The Chicago Food Depository:


4) Learn more here: http://www.chicagohomeless.org/

Feel free to post other homeless resources here in our comments. We can make a difference.

Wishing you a joyous holiday season.


With Lisa, and Gary