The Man Singing Outside Trader Joe’s
A Thanksgiving leadership reminder about seeing the people most others overlook
The best leadership lesson I learned one Thanksgiving week did not come from a boardroom, meeting room, or
It came from a homeless man singing outside a Trader Joe’s.
He was standing by the entrance, singing Christmas carols like he belonged on a stage. His voice stopped us in our tracks. Not because it was just “inspiring” in some cliché way... but because he was amazing and fully present in that moment.
We walked over, listened for a while, and then talked with him about his story.
His name was Delmar.
He seemed a bit surprised we would stop to talk to him, probably because he was obviously homeless with his belongings with him.. and also likely because he was a very large Black man in a predominantly white area of town.
He was sharp. Clear minded. articulate, and not out of it. Just a middle aged man down on his luck and living on the street. He knew the gospel and had optimism things would turn around in his life.
I would normally give food or supplies to help someone who was homeless, but we felt prompted to give him some money for his singing, pray for him, and encourage him a little.
It was one of those moments I will never forget. Then we went back to our warm car, our stocked fridge, and our long Thanksgiving to-do list.
And I remember feeling this deep, uncomfortable gratitude... not shame or guilt. The kind that forces you to admit how thin the line is between your life and someone else’s. I have been homeless, I have had hard times, I have experienced a lot of grief.
Here is what that moment reminded me as a leader:
The higher we rise, the easier it becomes to move through the world without really seeing the people around us or taking the time to have meaningful interactions.
The barista.
The security guard.
The cashier at the supermarket.
The contractor three levels down.
The person who feels invisible in your meetings.
Our loved ones.
Leaders are not measured only by how big their influence becomes. They are measured by how many people they are willing to notice and lift up on the way there.
This week, before we rush to the next thing, maybe we slow down long enough to really see the Delmars around us... at the store, at work, even in our own homes.
Who is one person you can slow down and genuinely notice this week?
Love this story.
I can completely identify with Delmar's situation. Thank you, Chris, for reminding me where I came from. I'm an ex-junkie and alcoholic who did 4 years in prison in NJ—been homeless and completely remembered wanting to die . That's how bad my situation had gotten. I spent my homeless days in Newark, NJ, and right here in Manhattan. Couldn't do the shelter scene, so I lived on the streets. I can remember spending my last piece of change on a bag of dope instead of getting myself something to eat. I can remember when I used to beg for pennies to feed my drug habit. Yes, I was that bad; you would know that if you looked at me now. However, my autobiography states that I'm trying to raise money to get it published. I don't think you know how many people I could help if they read my story. My autobiography is 1,000 pages of intense lifestyles and pitfalls. There wasn't much good in me for most of my life. Ot's a two-novel finished piece of fantastic writing. That's where I get most of my stories from. They come right out of my autobiography. God bless you and your family. And I hope Delmar can read my 2 novels at some point in his life.