My commute to work is a short, 10 minute walk in one direction. Along the way, I pass multiple eateries, clothing stores, Chicago’s largest public library, two pharmacies, and even a law school–all of this, squeezed into just 5 blocks worth of space.

I also pass over a dozen homeless people. Same path, same space. Every day.

Living in a city where encountering homeless people is the norm affects everyone differently. To some, it makes turning a blind eye a lot easier. To others, it evokes both pity and a desire to help. Personally, and a bit shamefully, I found myself experiencing a mix of both.


You can’t help everyone. That’s what I told myself when I bought a disabled, 37-year-old man named James a meal from a 7-Eleven, only to encounter another person in need half a block later. James had been sitting at a street corner and holding a plastic cup for change all day. When I saw him, he’d collected less than thirty cents. It was almost 7 PM, and he still hadn’t had a single meal.

An effective solution never involves giving away everything you have. Buying another meal for someone wouldn’t have been that, but to do so for every homeless person I saw would’ve. Donating food and money improves the individual situation without changing the system.

However, this logic prevented me from doing anything after that encounter. Realizing that giving away money is just a quick fix enabled me to use a veil of virtuous altruism to hide my unwillingness to confront this issue. I let the fact that homelessness is systemic impede generosity of any sort. And that’s definitely not the solution either.


I realized this while on a walk through Lurie Garden a few weekends ago. It was hot and sunny, and many people were dipping their feet in the fountains along the main walkway to cool off. It was a beautiful scene until I noticed the glimmer of coins in the water. Mostly pennies and a few dimes.

I instantly thought of James. There were more coins thrown into the corner of this fountain than dropped into the desperate, plastic cup that he relied on for basic sustenance. This was literal money water. And people were soaking their feet in it.


I draw this parallel not to shame them or anyone who throws money into fountains. It’s whimsical and fun, and to hate on people who do it would be both wrong and hypocritical. Instead, I want to reframe how many of us react to homelessness, including myself. It’s a wildly cyclic issue that has roots in our healthcare system, “need” to gentrify, and unforgiving business model. And while donating money or food won’t fix those, aid at any level is still beneficial. Just because you can’t help everyone doesn’t mean you shouldn’t help some.

If we can make a wish that may or may not come true on a coin and flick it playfully into a fountain, can’t we also spare at least that same amount for people who definitely need it?