Homeless in Wilmington. An Inspirational Story.

I was inspired by something that happened this past weekend. I thought I’d share this since there are lessons for business, leadership, life and humility that we all can learn from.

This is one of those posts where you wonder if it’s appropriate for LinkedIn or if it’s a Facebook or an Instagram post. Fully recognizing that if you have to wonder if it’s appropriate or not, it probably isn’t, I decided to post this anyway. I was so inspired by this that I thought it worth taking a chance on posting. I hope you agree.


I was driving from the NC shore back to Chapel Hill, NC this past Saturday evening and decided to stop in downtown Wilmington NC to have dinner. There is a nice restaurant with a nice bar there called Circa 1922 in case you’ve been.


I happened to find a nice parking spot near the restaurant with metered parking and I parallel parked and got out of my car. As it turns out, parking was free after 6:30 pm, but it was only 6:10 and I had no change. There was a parking app noted on the meter, but thinking it would take me longer to install the app, sign up and pay than it would to find change, I looked around to local stores where I could buy a pack of gum or something to get change.


As I was doing this, there was a young man sitting on the bench on the corner across the street who yelled over to me that parking was free after 6:30. I replied “Thank you, but it’s only 6:10 and I don’t have any change”). His response was “Oh, I have change you can use.” He then proceeded to walk over and hand me enough change to get me to 6:30.


I of course said thank you and asked him what he was doing downtown. He replied that he was homeless, that he had a medical condition (he was wearing a heart monitoring device of some sort) and was happy that it was such a warm evening. I shook his hand, said thank you again and proceeded to talk with him for a couple of minutes. He was seemingly sober, bright, articulate, but clearly had medical issues. I was so touched by his generosity that I gave him all the cash I had, which wasn’t much (at least it wasn’t to me, he seemed especially grateful).

But the story and lessons certainly don’t end here.


I went on my way to my nice restaurant. I sat down and started to tell this story to the bartender. Then I thought to myself:

Here I am sitting at a nice restaurant, dinner ordered, glass of wine in hand and someone down on their luck and homeless gave ME money to fill my parking meter so I could park my nice car on my way to my nice dinner and all I could do for him was to give him some cash.

So, I went back out. Not more than 5 minutes had gone by. I wanted to ask him to join me or buy him dinner somewhere else, whatever I could do to help. He was gone. I walked around and couldn’t find him.


I went back, finished my dinner and walked around some more after hoping to find him. I couldn’t. Maybe he used the cash to buy dinner and he was sitting down over a nice meal. Maybe he used it for something not as constructive, I will never know.


But I walked away inspired by him, by his actions and disappointed in myself that I didn’t act more quickly to do more. So, I thought to post this with the hope that the lessons from this might help us to be better leaders, better managers, better people.

My take-aways (and I am sure I am missing countless others):


1. Act. Now. If you miss an opportunity to do something, it may be gone forever.

2. If you miss an opportunity, use it. Give somewhere else, teach someone else, return the favor somewhere else, post to tell others. Miss an opportunity that you regret, give back elsewhere.

3. Examples of Leadership are all around us. Lessons in generosity, taking charge, sharing one’s own experiences and being open can come from anywhere. Here, someone on the street taught me priceless lessons that warm night in Wilmington.

4. We’re all equal. No matter where you are on your org chart, you are no better or worse than someone above or below you on that chart – and certainly not because of your position on the org chart. One tech company famously asks job candidates to provide the first name of the receptionist that greeted them in the lobby because the ability to do so says something about them as a person and about their attention to detail. That night in Wilmington, I learned that that homeless person was a far better man than me that night – more generous, caring and open – willing to help a total stranger out of the blue.

5. Lead by example. He led me that night and I learned that doing is the best kind of leadership.

6. Priorities. His priority was helping. Even if it meant losing some of the change he accumulated that evening to help a stranger, his priorities were to help first, hoard last. Maybe as we accumulate stuff – titles and pay at work and material things at home – we all can learn from that.


I am sure that there are countless other lessons that I’ve missed as well as cynical views on what transpired that night, but I would argue that if we all did a bit more of what that one gentleman did for me that evening every day, we’d be better leaders, better managers, better humans as a result. I hope this story inspires you as it did me.


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