CIW Attendees Learn Life Lessons from Malcolm Gladwell, Ben Rattray and More

Throngs of people flock to the Cadillac Palace Theatre for CIW’s Lessons: The Choice is Yours Talk on Oct. 14.
As the music got louder and the two-minute countdown projected onto the screen, people hustled into the Cadillac Palace Theatre, shuffling among several white “Reserved for you!” signs to find their seats for Chicago Ideas Week’s Lessons: The Choice is Yours Talk on Oct. 14.
Ben Rattray, founder and CEO of, and Malcolm Gladwell, New York Times the best-selling author and staff writer at The New Yorker, were just a few of the dynamic speakers to take the stage that Monday night. The event was one of 24 Talks and more than 100 events taking place across the Windy City as part of CIW’s weeklong innovation festival each October.
Brad Keywell, founder and co-chairman of CIW, kicked off the evening by asking the audience to introduce themselves to someone they didn’t know – because CIW was all about unexpected connections.
“Tonight you are in a classroom for storytelling, reflection and imagination,” he said.
Gladwell shared the different ways of looking at the 300-year-old story of David and Goliath that he found while writing David and Goliath: Underdogs, Misfits and the Art of Battling Giants – and the lessons that can be gleaned from it.
Malcolm Gladwell chats on camera backstage.
“The mistake we make is being passive in the face of what we assume are insurmountable obstacles,” Gladwell said backstage. “The thing about David is he refuses to believe the battle is over, which I think is a lovely lesson for all of us.”
Rather than viewing David as a naive boy with a slingshot, he told the packed room that he saw him as someone with an innovative, deadly weapon. And Gladwell said he saw Goliath as a mere mortal with a pituitary tumor that made him grow to a massive size as opposed to him being a terrifying giant.
“Giants are not what they seem, and sometimes shepherds have a sling in their pocket,” Gladwell said.
Ben Rattray shared how he changed his perspective on life after his brother told him he was gay – and that the most painful part for his brother wasn’t people who were anti-gay, but those who did nothing at all.
“That night, I realized I wanted to serve others and myself,” said Rattray, who changed course from becoming an investment banker to founding, a website that promotes social change through online petitions.
Catherine Hoke then shared lessons she learned on her way to launching Defy Ventures, an entrepreneurship program and incubator  that helps felons like high-ranking drug dealers start legal businesses after being released from prison.
Omar Cantwell, a 39-year-old Defy Ventures graduate, took the stage and told the audience how he grew up in poverty and associated violence with manhood. He said he wanted to change and show young men that other lifestyles are possible – with Defy’s help, he started an industrial kitchen cleaning business.
“Surprisingly I wasn’t nervous, but that had a lot to do with the preparation we took beforehand, just to get used to telling our story, especially the difficult parts about our backgrounds. It took a lot of repetition just to be comfortable sharing that,” he said.
The audience’s support radiated through their loud applause.
“What you think is going to be the obvious highlight of the night isn’t necessarily always the case – it’s the people who you wouldn’t really expect it to be,” said CIW attendee Justin Winget, 33, of Chicago. “I think hearing those stories and the power behind those was really just amazing.”
Speakers share their personal stories and life lessons before a full house.
After Hoke’s Talk, Rattray interviewed stand-up comedian, Tig Notaro. Backstage she said she wanted people to walk away from her discussion knowing that everything in life is ultimately manageable.
I just love that I’ve been given this opportunity to use my comedy in a way that I just have never thought to do,” Notaro said.
She shared her chain of earth-shattering event, ranging from her mother passing away to being diagnosed with cancer – and how she never gave up. While her tale was tragic, she had the crowd laughing the entire time.
“…Then I got cancer, and I was like, ‘Okay. Now everything’s hilarious,’” she said.
CIW volunteer and Chicagoan Michelle Gilio, 46, said Notaro’s story resonated with her.
“Just hearing Tig talk about going through so much,” Gilio said. “And it was the funniest thing, she’s saying, ‘I was already a happy person, this [lesson] was wasted on someone.’ ”
Backstage speaker Josh Kilmer-Purcell, the best-selling author and reality show co-star of The Fabulous Beekman Boys, said he
“My agenda with my speaking tonight is to get people think a little more broadly about the lessons that they learn in life, that they’re not as concrete as people think,” he said.
Onstage Kilmer Purcell discussed the “non-lessons” he learned from his parents and other experiences over the years – from his years as a drag queen to Planet Green cancelling his reality show to what it took to win CBS’ game show The Amazing Race.
“We treat our lessons as fences,” he said. “I used them as guideposts.”
As the speakers finished their presentations, the crowds filed out of the theater, and many headed straight for the book signings.
“What I saw a lot of was that these [speakers] are everyday man who stops trying to fit in and decides to tread a path on their own, and just be dedicated and devoted to that path,” said CIW volunteer Muriel Jackson, 50, of Chicago.

*Check out in January to see full videos of  the Talks each of our dynamic speakers gave!*

Written by: Marlee Septak
Sara Serritella contributed to this story.

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