Standing in the heart of downtown Chicago, in front of “The Flamingo” on Dearborn Street, junior Caleb Richards lines up his board for a trick he’s been practicing all week. The board rattles beneath his feet as he rolls across the pavement, heart pounding as he focuses on the trick before him. 

Over the past years, skateboarding has become an integral part of Caleb’s life and daily routine, giving him a creative outlet and helping him connect with a community.

Caleb’s fascination with skateboarding began with his cousin, who skated frequently around him when Caleb was younger. When Caleb was in eighth grade, his cousin bought him his first skateboard. 

Even with a new skateboard, Caleb didn’t begin skateboarding until ninth grade. He began looking for places to skateboard in downtown Chicago  and set a regular schedule for himself to skate.

“As I’ve gotten better, it’s opened my eyes up in a way, and now that I have these skills at skating, I realize how much I can do when I push myself,” Caleb said.

As he’s continued to hone his skills, Caleb has enjoyed the freedom that comes with skateboarding. Namely, he enjoys that the sport offers him an outlet to exercise his artistic creativity through skating. One way he demonstrates this creativity is through the videos he records and edits of his friends skateboarding, which has quickly become another favorite hobby of his.

“Not only is it fun to learn new tricks, you can choose what tricks you want to learn. You can also pick where you want to skate, and when I’m filming, I can pick how I want to edit it,” Caleb said.

This past summer, Caleb participated in an After School Matters program about skateboarding, and earned money by skateboarding and spending time with other skateboarders.

“I got paid to just go hang out and skate with my friends every day, and it helped me improve so much and get out of my comfort zone,” Caleb said.

Through the After School Matters program and practicing in Hyde Park, Caleb has met many other teenagers interested in skateboarding. He now considers skating as a social sport, and said that anybody can be a part of the skateboarding community.

“There’s so many ways you can be creative with skateboarding, and everybody has their own specific style, and anybody can be a part of the culture and do what they want,” Caleb said.

As the sun sets over downtown Chicago, and Caleb packs up his skateboard to leave, he reminisces over the new skills he’s learned and the people he has met.