The $5 Lesson: What a Homeless Man Taught Me About True Wealth

It was a gray Thursday morning when I encountered the man who would unknowingly reshape my perspective on life. The kind of morning where the sky forgets the sun exists, and the coffee you sip tastes more like obligation than comfort.

I was walking to my office downtown, dodging puddles and mentally preparing for a meeting I wasn't looking forward to. My mind was buried beneath a pile of spreadsheets and deadlines when I spotted him—a man sitting cross-legged near the corner of 5th and Main. He had a thick, unruly beard and wore a faded army jacket that looked older than me. A cardboard sign rested against his knees:

“I don’t want your pity. Just hungry.”

There was something disarmingly honest about it. No dramatics. No manipulation. Just truth.

As I passed him, I felt that familiar tug of guilt. I reached into my pocket and found a crumpled $5 bill. Not much, really. Just enough to feel like I’d done something without disrupting my day.

I handed it to him silently and began walking away.

"Hey!" he called out.

I turned, expecting a simple thank you.

Instead, he stood up, smiled, and said, “You hungry?”

I was caught off guard. “Uh… what?”

“I’m headed to the food truck across the street. Best breakfast burritos in the city. You bought mine—least I can do is buy yours.”

I laughed awkwardly. “No, man, that’s your money. Get yourself something warm.”

But he was already walking. “C’mon,” he waved. “Don’t make me eat alone.”

Against my better judgment—or maybe because of it—I followed him. We crossed the street together, this odd pair: me in my blazer and slacks, him with boots that had more holes than sole.

We ordered two burritos. He paid with the five I had given him, adding a few coins from his own pocket. When the food came, we sat on a bench nearby, the city buzzing indifferently around us.

“My name’s Curtis,” he said, unwrapping his burrito with the kind of reverence usually reserved for Christmas gifts.

“Jason,” I replied.

We ate in silence for a moment. The burrito was excellent. But what struck me more was how Curtis ate. Slowly. Appreciatively. Like every bite mattered.

“So what do you do, Jason?” he asked between bites.

“I work in finance,” I said, suddenly self-conscious. “You?”

He chuckled. “Survive.”

I nodded, unsure of how to respond.

But Curtis wasn’t bitter. In fact, he smiled more than most people I knew. He told me he’d been living on the streets for a little over two years. Lost his job after a warehouse fire, then his apartment, then his wife—who couldn’t handle the spiral.

“I used to think money was everything,” he said, wiping his hands on a napkin. “Turns out, it’s not. Don’t get me wrong, it helps. But it’s not what keeps you warm at night. Not really.”

I listened as he talked about the small acts of kindness he’d seen—the woman who brought him socks every winter, the teenager who gave him her lunch, the barber who offered free haircuts to anyone willing to wait.

“There’s wealth,” Curtis said, “and then there’s riches. Wealth’s not always in your wallet.”

That line stayed with me.

After we finished eating, I offered to get him something else—coffee, maybe. But he declined.

“You’ve done enough,” he said. “More than most.”

We shook hands. His grip was firm, warm.

And then, just like that, I returned to my office and Curtis returned to the street.

But I wasn’t the same.

That evening, I found myself thinking about Curtis. About how I had handed him money assuming he needed me, when in truth, I was the one who needed that encounter.

Over the next few weeks, I began noticing things I hadn’t before. The janitor at my office building who always smiled despite working double shifts. The bus driver who kept candy for kids. The barista who remembered every regular’s name.

I started carrying a few spare bills in my wallet—not out of guilt, but readiness. I began volunteering at a shelter on weekends. Not to be a savior. Just to connect.

And I started measuring wealth differently. Not in bank balances, but in breakfasts shared. In conversations held. In lessons learned from people like Curtis, who owned nothing yet gave so much.

It’s been over a year since that morning. I haven’t seen Curtis again. Sometimes I wonder where he is, if he’s okay, if he remembers the guy in the blazer who walked with him to a food truck.

I hope he does.

Because I’ll never forget him.