Dedicated Dads: Mike Leonard

Tom Brokaw calls Winnetka’s Mike Leonard a national treasure.

Meanwhile, Leonard calls himself very imperfect and proud of it. Those “flaws” led to the creative and family success underpinning his national treasure status.

This father of four, whose tightly-knit family is known for high-jinx, laughter, video cameras and whiffle ball, has been a feature reporter on NBC’s Today Show for 30 years.

His endearing, hilarious book about the year he spent touring the U.S. in two motor homes with his wife, Kathy, young adult children and “crazy” 80-something parents, “The Ride of Our Lives : Roadside Lessons Of An American Family” (Ballantine Books, 2007) became a best-seller. He wouldn’t know if it made him rich, though, because, as he repeats throughout our long interview: “I don’t do financial stuff.”

And he didn’t do much of anything likely to build self-confidence as a short kid and poor student growing up at Sacred Heart Grade School and Loyola Academy, he says. “I was terrified to raise my hand in school, because I never knew the answers,” he explains, “I only earned 300s in math and 400s in English for the SATs. I kept asking myself, ‘What the hell am I cut out to do?’”

The answer came at a poorly attended Ravinia concert during the summer of 1964, when Leonard was about 17. “Like me, Bob Dylan was skinny, curly-haired and not very popular,” he recalls. But Dylan’s songs told stories that resonated.

“That night I decided to be creative,” Leonard says. He bought a movie camera and began creating short, poignant films.

It took another 17 years—most of them lived in Arizona on the edge of poverty with his wife and young children—before he landed on “The Today Show” and eventually co-owning Picture Show Films, a Chicago production company, with his children.

Leonard believes his open attitude about his own weaknesses and failures made him a better, more empathic parent. And his quest to carve out a creative living demonstrated his belief that “opportunity is like a subtle wind floating past you. To feel that wind, you have to take off the imaginary coat that hides your scars of imperfection.”

He adds, “You will also feel the fear of failure. But every attempt to better ourselves will include failures.”

Editor’s note: To see Leonard’s creative story telling in action, watch this segment from “The Today Show” on Capannari Ice Cream, a Mt. Prospect favorite.

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