After a recent awards ceremony, I approached a fellow recipient and extended my congratulations and my appreciation. The former was an acknowledgement for her outstanding performance in achieving excellence in her work. My appreciation, however, was more personal. It was my heartfelt thanks for how her institution — a library — was a part of my survival as a young adult. For a month or more I lived in that library, moving from floor to floor across the night time hours, avoiding the din of vacuum cleaners and crews charged with maintaining the facility. I showered early and kept some clothes in lockers in the field house and ate what I could in the student union.

The look on her face when I extended my thanks spoke volumes. Although I was decked out in my finest attire, her face shifted from the pleasure of my congratulations to near disgust over the reality of my former homelessness. I have seen this look before. Though I don’t recall the particulars, I know I learned it as a very young child when we needed something to survive the cold, hunger, something.

I recall the look, too, when I applied for food stamps when a strike went on longer than I had resources to manage. Recently the look was again right in my face.

Each day that I travel to Chicago for work, I walk one of three ways to get to different consultees with whom I work. On the way to one organization, I see a man with no legs and one partial arm ask for money. He clutches a plastic cup to his torso with the stump of one arm. He does not look up. He has no cardboard that signals that he is a veteran or homeless. He is unshaven. His body odor is very strong.

Walking another way, I see a different guy. He parks his wheelchair in pedestrian traffic and props next to it a sign that indicates that he is a veteran. His guide dog rests on the pavement. The man is blind.

Where ever I am working, however, most days I take an identical route back to Union Station. I do this to increase the likelihood that I will see Ray, Susan, Robert, and another man who does not share his name. These are my friends. One has an address. Two live in shelters when they can, but the addresses are irregular so they don’t use them. They are all homeless.

A few weeks ago I had time for a longer conversation with Susan. She is taking some community classes to qualify as a childcare worker. She remains concerned that the lack of so many teeth will dissuade agencies from hiring her, but she hopes to figure that out along the way. We were huddled in conversation out of the way of pedestrian traffic, avoiding the gusts of wind off the river near the station. Someone crashed into me as she passed, likely in a thoughtless rush to her commuter train. Minutes later, it happened again — this time a man concentrating on his phone. Susan recommended we move still further away but directly facing into the wind.

As we turned, I was clearly shoulder checked by another passer by. When I looked up, I saw the look, right in my face. Disgust. When I started to complain, Susan grabbed my arm and pulled me away. She said that this happened all the time and not to let it bother me.

My first thought was about my attire. Did I look homeless, too?

Within seconds, the realities of that thought came crashing in on me. At some deep level, I could wrap my head around mistreatment or invisibility if I looked homeless. Despite my numerous decisions to extend friendship and personal connections with people who experience homelessness, I found myself understanding their marginalization. Even though I knew temporary homelessness a couple of times in my life, I carried with me still some unspoken and oversimplified sense of responsibility for those experiences.

Learning more about homelessness from the Illinois Poverty Report has helped put homeless into some perspective. My friend Julie Bock has also helped with some simple definitions upon which I can rely. But I remain at a loss to make much of difference. I have even begun to calculate what it would cost to house the estimated 550,000 homeless people in the US. I think between $5 and $10 Billion could make a huge dent in that figure. That is roughly 1% of holiday retail shopping expenditures in the US.

This befuddlement is one reason I rely on the intelligent work of Heartland Housing. Their residences in Chicago, Madison, and Milwaukee provide quality, stable housing to thousands who would be hard pressed to find more respectful interactions. In Milwaukee, Heartland partners with Guest House and Capuchins at St. Ben’s. Michael Goldberg and his amazing team are supported by a solid and capable Board of Directors. It has been helpful for me to learn more about their work, to contribute to their efforts, and to continue to question my own feelings of helplessness in the face of the enormity of the issues.

How do you respond to homelessness? Are there places where you feel hopeless about making a difference? How did you come to that position? It would be great to keep the conversation going online here or through social media.