Food Deliveries and Startup Dreams in Chicago

A smiling young man with a beard, wearing a hoodie and a jacket, standing on a busy city street.

“I’m 27, currently living in Chicago, trying to make ends meet by doing food deliveries. It’s not exactly what I imagined doing with my business degree, but hey, you gotta do what you gotta do, right? My days start around 10 AM, which is late for most, but my nights run long. I’m out on my bike till midnight sometimes, navigating the city streets, dropping off everything from deep-dish pizzas to Thai curries. The job’s unpredictable, sometimes I make good money, other times it’s just enough to get by. It’s tough not having a steady job, but it gives me the flexibility to work on my startup ideas. I’m working on an app that connects local farmers to urban residents for fresh produce delivery. It’s still in the early stages, but I’m hopeful. My family back in Atlanta worries about me, but they support me. I miss home, especially my mom’s cooking. Here, I mostly eat on the go – lots of quick bites from street vendors. One of my favorites is a place called The Tamale Guy, where I grab tamales filled with beans and cheese, wrapped in corn husks. I’ve made a few friends among other delivery folks, and we often share tips on good spots to eat. My girlfriend’s a nurse, working crazy hours too, so we hardly get to see each other, but we make it work. She’s my rock. For now, my goal is to stabilize my income, get my app off the ground, and maybe finally take that vacation we’ve been dreaming about. The hustle is real, but I’m learning a lot about resilience and making the most out of every opportunity. When things get overwhelming, I remind myself of my favorite comfort food, shrimp and grits from a spot back home. It brings a sense of nostalgia and motivation to keep pushing forward.”

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