One of the hardest parts of being a Chicago photographer isn’t taking the photos. It’s finding the next opportunity. There are slow seasons, algorithm changes, and days when you wonder where your next inquiry will come from. This is the story of how one TikTok DM led to photographing Chi Picnic Club and reminded me that sometimes all it takes is putting yourself out there.

Like most nights, I was lying in bed scrolling through TikTok when a profile caught my attention. TikTok had recommended Chi Picnic Club, and I was immediately intrigued. Their aesthetic felt intentional, their content looked polished, and the entire concept was something I could genuinely see myself photographing. It didn’t feel like a random business. It felt like one of those accounts where you immediately think, “I’d love to work with them someday.”

Rather than overthinking it, I opened my messages and introduced myself.

To my surprise, I didn’t have to wait long. One of the hosts, Ben, replied saying they had an event happening that Saturday. It was only Thursday, but suddenly I had plans to photograph a lakeside picnic overlooking the Chicago skyline. I immediately said yes.

Walking into a collaboration with people you’ve never met can be intimidating. I wanted to make a good first impression while also staying true to my photography style. Thankfully, the moment I arrived, everyone was incredibly welcoming.

Little did I know, this wasn’t where our collaboration would end. Since that first picnic, I’ve had the opportunity to photograph multiple events for Ben and Janniel, the hosts of Chi Picnic Club. One of my favorite full circle moments happened while I was photographing a maternity session at the same park where Janniel was setting up a surprise proposal picnic. We unexpectedly ran into each other while working completely separate events. It was a small reminder of how connected Chicago’s creative community can be.

If you’ve been looking for a unique way to meet new people in Chicago, keep an eye out for Chi Picnic Club’s upcoming events. Their picnics are thoughtfully planned, incredibly welcoming, and always seem to sell out fast.

One of my favorite things about Chi Picnic Club is that you can show up alone and leave feeling like you’re part of a community. In a city as big as Chicago, that’s something really special.