(WBBM NEWSRADIO) – Chicago photographer Lenny Gilmore has been living a little dangerously for well over a year by spending a portion of each day on roller skates.
There’s a point to this, he says.
“It’s okay to fall, it’s okay to get a little bit hurt,” Gilmore tells Looped In: Chicago. “We all have to take a calculated risk with that, but I think we shouldn’t let those fears stop us from finding joy in our lives and in the world.”
The Batavia native and former Red Eye photographer is known for his portraits of celebrities, including Chicago musicians Chance the Rapper, Jeff Tweedy and Chief Keef and actors Michael Shannon and Rebecca Ferguson.
His current fascination with skating – from traditional roller skating to roller blading – dates back to 2015. That’s when the former hockey player laced up some roller skates while shooting a story about a women’s roller derby team in Chicago. He recalls being more than respectable on wheels.
“That kind of got me thinking about it. Then, I moved out to California for two years. Skate culture was just everywhere there.”
Fast forward to a few years ago when he became interested in the idea of rollerblading the RAGBRAI course in Iowa. After attempting a leg of the course with mixed results, Gilmore said he hit the reset button by committing to roller skating every day to stay conditioned. His modus operandi is to make small improvements to his form and not worry about going vertical or doing dangerous jumps. He takes video of many of his runs.
“Skating is just a pure act of joy,” Gilmore says, using that word often. “It’s kind of how I found community. I found creative collaboration and exercise. Anywhere I go in the world I can find someone who wants to roller skate.”
His consecutive streak of daily skating sessions, which he has done across an array of settings, brought him earlier this week to the WBBM Newsradio studios at Prudential Center. He marked his 500th day on wheels; that tally continues.

Now, Gilmore has spun his passion for roller skating into a children’s book, “If You Roller Skated the World,” which has an environmental message. It’s also meant encourage young people to set aside their fears of the unknown, he says.
“I want this book to kind of encourage kids to find their passport, find their excuse to go see the world, see what’s out there.”
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