Milwaukee Avenue

A song about late-night Chicago, growing up in motion, and the streets that teach you who you’re becoming.

Milwaukee Avenue became one of the first places in Chicago that felt like it was speaking directly to me.

When I was new to the city, I used to walk around Logan Square just taking everything in. The bars, the bikes, the murals, the train noise, the little shops still glowing after dark, people spilling out of venues, the smell of food, smoke, rain and cheap beer in the air. It felt completely different from Watseka, where you could hear your own thoughts too loudly.

In Chicago, everything moved. That movement was exciting, but it was also overwhelming. I was trying to become independent, trying to write better songs, trying to make friends, trying to earn money, trying to stop feeling like I had arrived by accident.

Milwaukee Avenue is about that feeling of walking through the city at night and realising the place is changing you. Not all at once. Not dramatically. Just little by little, block by block.

It’s a song about being young in a city that doesn’t slow down for your uncertainty. You either learn the rhythm or you get swallowed by it. I think, somewhere along that street, I started learning mine.