What $1 Can Buy

This is a story about an experiment in giving.

I’m used to walking down the street and seeing someone sitting on the sidewalk with a sign:

“Homeless. Please Help.”

And I feel it—that tension. That deep, emotional tug to help.

But then the mental calculus starts. There are so many great causes I could be supporting with that dollar. I could give to a food pantry. Or support addiction recovery. Or donate to a shelter with wraparound services. Or contribute to an organization that tackles root causes like housing policy or mental health care.

I don’t.

But I could.

And so what do I do?

I keep walking.

That’s the problem. There are so many good options that I end up doing… none of them. We want to be the best possible people, making the most effective possible choices. And it’s paralyzing.

But recently, I started seeing it differently. Instead of viewing people asking for help as a distraction from my “real” philanthropy, I began to see them as an opportunity. A human opportunity.

So I decided to stop arguing with the urge to help—and just go with it.

Here’s what I do now: I carry a single dollar bill in the change pocket of my jeans. Not in my wallet. Not tucked away in some back compartment. It’s ready. When I walk past someone who asks for help and I feel that flicker of generosity—that moment that usually gets smothered by guilt or analysis—I give the dollar.

And then later, I replace it. And I write down what I saw.

I still give to other causes. I still care about systemic solutions. But this small act? It’s become something more than a transaction. It’s a moment of presence.

Are there better causes? Yes.
Am I overwhelmed by them? Also yes.
Will this dollar be used well? Maybe. Maybe not.

It reminds me of a moment from Aaron Sorkin’s Sports Night:

Isaac: Every morning I leave and acre and a half of the most beautiful property in New Canaan. Get on a train and come to work in a 54 story glass hi-rise. In between, I step over bodies to get here. 20, 30, 50 of them a day. So as I’m stepping over them, I reach into my pocket and give them whatever I’ve got.

Dan: You’re not afraid they’re going to spend it on booze?

Isaac: I’m hoping their going to spend it on booze. Look, Danny, for these people, most of them, it’s not like they’re one hot meal from turning it around. For most of them, the clock’s pretty much run out. You’ll be home soon enough. What’s wrong with giving them a little novocaine to get them through the night?

Sports Night Season 1 Episode 9: The Quality of Mercy at 29K

That line has stayed with me.

Because giving—even just a dollar—feels good. And not in a self-congratulatory way. It feels human. Sacred, even. Maybe that sacredness comes from the Lubavitcher Rebbe and his single-dollar bills.

Rabbi Menachem Mendel Schneerson, known as the Lubavitcher Rebbe, led the Chabad-Lubavitch movement from 1951 until his death in 1994 and became one of the most influential Jewish leaders of the 20th century. In 1986, he began a weekly tradition that became iconic: every Sunday, he would stand for hours outside his Brooklyn headquarters at 770 Eastern Parkway, handing a single dollar bill to each visitor along with a blessing and a request—to give it to charity. The goal, he said, was that “when two people meet, it should benefit a third.” These lines often stretched for blocks, and the exchange was brief but personal, forming a spiritual moment of intention, presence, and shared responsibility.

While the dollar had little material value, the gesture took on profound symbolic weight. Many recipients donated a different dollar and kept the Rebbe’s as a cherished keepsake—some even passed them down across generations. The act served as a reminder that even the smallest gesture, when offered with sincerity and purpose, could inspire kindness and create lasting meaning.

I think that’s what I’m trying to do. Pause. Choose. Give.

Not because it’s the most effective thing I could do.

But because it’s something I will do.

And sometimes, that’s enough.