About 8:30 last Sunday evening, I was weaving my way through other walkers on Wacker Drive- which, as a riverfront path, is arguably one of the busiest pedestrian routes in Chicago on a summer weekend evening- when a long-haired and bearded young man in a canvas jacket and blue jeans strode passed me, speaking to no one in particular.

“Well, I guess it’s time to get ready for bed.”

I processed his words for a moment as I walked and several yards later, I came across a rolled-out sleeping bag and a furniture pillow sitting on some flat cardboard. I ambled on, past a strolling young couple in dress attire, holding hands, and then a mother and daughter taking in the lights along the river. I stopped walking and decided to go back and see if the young man verified my conclusion. I found a seat on a bench near the bedding spot and waited.

And I snapped a photo of this riverside accommodation.

People sauntered by on the sidewalk. Waves of cars passed on the road to my right. And in a short time, the young man returned from wherever he did his bedtime routine, sat down on his bed, and removed his jacket and his boots and, disregarding the bustle around him, was prepared to go to sleep.

Before he had a chance to shut it down for the night, I was compelled to go over and say “Hi” to him.

I learned his name was Phil. He was from St. Louis. He was in Chicago because his wanderings had landed him there. He was biding his time to find a way- and money- to get back home. He credited a church in town with helping him to survive for a little while and to find hope for each day. He was friendly and amenable. He didn’t ask for anything. We just talked briefly about his experiences and journey. And I thought about how hard life can be, and how close homelessness could be to many unsuspecting people.

As our chat wound down, I quietly gave him $20 as I shook his hand and asked him to get a good meal in the morning. He said the money would help him for a few days, and he was grateful. I also asked him if I could get a picture of him- for me- so I could remember him. He said thank you, yes, that would be great. I wished him safety and godspeed in his return to St. Louis.

And after leaving him, as I headed back across the Loop for my AirBnB room and bed, I realized that that moment was probably the most important experience I would have on my trip in Chicago.

And it was.

Take care, Phil.