Homeless Encounters


The weather was bitterly cold and the skies were still dark.

I could now see more clearly, there was indeed a homeless person outside, bundled up against the building's concrete outcropping. Here we go. I grabbed the breakfast and got out of my car. I walked up to the pile of blankets, with some hesitation and anxiety, but managed to say, “Good morning. I’ve brought you some hot breakfast and orange juice.” 

Dirty fingers emerged and pulled back the covers just a bit, revealing the face of a middle-aged woman. I smiled and repeated, “I’ve brought you some orange juice and hot breakfast.” Her eyes welled up with tears, and she said, “Thank you.” I could tell that she really meant it. She took the items from my hands and pulled them under the covers with her. I wished her well, told her that her Creator was aware of her and loved her. She smiled a pained kind of smile, shed a few more tears and said, “God bless you…”

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Thus began a practice that would continue for the next six months. Some of the experiences I had were especially poignant. Allow me to share a few highlights from the daily experiences I had encountering the homeless. 

One morning I brought breakfast to John (not his real name) who told me the most startling story. Just ten years prior, he had been a successful entrepreneur with a number of burgeoning businesses. He was embarking on an ambitious expansion when the economy unexpectedly tanked in 2007-2008. Being precariously overleveraged at the time, he lost everything. Not only did he lose his businesses, but he also lost his home and eventually his family. 

Now he was living on the street. His demeanor suggested a man who was still intelligent, but beaten down by painful losses. We sat together for a while as I listened to his story. I offered encouragement as he wistfully spoke about trying to rebuild in some way. He said he appreciated having someone listen to him, and was grateful for a hot breakfast on that cold winter morning...

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