Overheard at Chicago Ideas Week


Last week the city of Chicago was overtaken by the 3rd annual Chicago Ideas Week--a weeklong series of presentations, workshops, and interviews designed to, as their website says, “inspire, connect, and activate the city of Chicago and beyond...the global hub for new ideas, an ecosystem for innovation and a playground of intellectual recreation.”

That’s a whole lot of fancy buzzwords. Having never been to any part of CIW in years one and two, I decided this year I would take part in the ‘intellectual recreation’ and attended three different sessions:


Edison Talks (a day-long series of speeches and interviews around the theme of “Departure”)

Hip Hop: Movement Beyond The Music

Here are some notable quotables and happenings from the folks on stage during my experience at Chicago Ideas Week. Note: Many of these quotes have been paraphrased because I could only write so fast while sitting and listening.



  • CIW Founder and Keynote Speaker Brad Keywell introduced the evening by asking everyone in the audience to take 30 seconds and introduce themselves to someone nearby. “See if you fit in their plans.”


Edison Talks


  • “Life starts after your major departure.”

    • Mike Wilbon. Co-host Pardon The Interruption, Analyst ABC & ESPN

  • “Retirement is about finding something that fulfills you.”

    • Grant Hill. Seven-time NBA All-Star, Film Producer, Philanthropist

  • Wilbon and Hill also talked at length about the misconception people have when professional athletes appear to ‘fail’ at retirement. They talked about how many people don’t realize or don’t want to acknowledge that it is tough for an athlete to completely remove themselves from the one thing that has validated their identity since puberty.

  • “The education system is not broken, it’s obsolete.”

    • Naveen Jain. Founder & CEO inome

  • “If we found out that there was a shortage of oxygen, we wouldn’t ask people to breathe less, we would find a way to create more oxygen...We must solve problems with an abundance approach.”

    • Naveen Jain

  • “I am intuitively more me, than other people are them.”

    • M. Night Shyamalan. Screenwriter, Director, Producer, Author I Got Schooled


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  • Musician and founder of Big Muse Peter Himmelman asked everyone to take out their phones, choose someone they love, and write a letter telling them they love them via email or text message.

  • “3 Lessons from the Undead: 1) Not everything that is terrifying is meaningful, but everything that is meaningful is terrifying. 2) Don’t be a hater. Be active, not destructive. 3) The only thing that allows us to transcend death is love.

    • Charity Tilleman-Dick. Soprano, Composer & Writer, and only opera singer to be the recipient of two double-lung transplants. (Her lessons from the undead refer to things she learned while in a coma for over 30 days after one of her transplant surgeries.)

Hip Hop: Movement Beyond The Music

  • “The media puts the spotlight on the 2% that’s wrong with Hip Hop”

    • Toni Blackman. Rapper, Actress, Writer, State Department Musical Ambassador on the misperception that there is a universal problem with the genre of Hip Hop

  • “There’s a problem when I walk down North Avenue between Damen and Ashland, what used to be primarily Puerto Rican...and all I see are million dollar condos and hipsters in skinny jeans. What happened to the people? What happened to the family?”

    • Boogie McClarin. Hip Hop Dancer & Faculty, Old Town School of Music on the larger issue of gentrification in Chicago

  • “Stop ignoring people because you think they can’t help you, start reaching out.”

    • Boogie McClarin on the concept of rebuilding the sense of community

  • “Stop worrying about Obama and call your alderman and fix what’s wrong in your community.”

    • Boogie McClarin on the concept of rebuilding a community, and focusing efforts in the right places

  • “Hip Hop is like a 3-course meal...you can have your appetizers if you aren’t too sure about the menu but just want a taste. These were the Will Smiths and Queen Latifahs. Happy Rap, I like to call it...then you have your main course, your conscious rappers, the ones bringing up issues and telling stories...this is your meat and vegetables…then you have dessert. This is the pop bottles and party music. Now dessert is fine as long as you have a well-balance meal, but the problem is that we’re only eating dessert. People are having dessert for breakfast, dessert for lunch, dessert for dinner, dessert for dessert...and that’s unhealthy...We cleared the table and all that was left was dessert.”

    • Brother Ali. Hip Hop Artist, Speaker, and Activist assessing the landscape of hip hop and how ‘mainstream’ became mainstream

  • “We must be intentional about our equity.”

    • Brother Ali on how artists and fans can bring back a ‘balanced diet of Hip Hop’

  • “Next time you go to a show, look around and ask yourself, “Do these artists look like me? Do the people here look like me?” If they do, then make an effort to diversify your tastes.”

    • Brother Ali on shifting Hip Hop from Colonial Capitalist to Cultural Catalyst


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All in all, I enjoyed my time at Chicago Ideas Week. Certain sessions inspired me, and others challenged me to re-evaluate opinions or norms. I had the opportunity to meet Malcolm Gladwell for a brief moment, engage in sound conversation with Jessica Buchanan and Erik Landemalm (co-authors of the New York Times best-seller Impossible Odds--if you haven't heard of them, Google them. They have an amazing story), and eat lunch with a founder at 1871, a Partner at an NYC-based law firm, and a group of Venture Capitalists.

Here’s where Ideas Week comes up short, though: I met those people and had those conversations because I made them happen. hundreds of people lined up to have Gladwell sign their copy of David & Goliath, but I made a decision to not just stand there and wait for his autograph, but tell him I founded Idea Lemon and I will meet him again because I believe in our success. I took it upon myself to tell Buchanan and Landemalm that their story inspired me and I truly felt for them as they shared on stage what it was like to be held hostage by Somali Pirates. This personal connection we established piqued their interest in who I am, and we began a five-minute discussion about Idea Lemon and our personal branding consultations. At lunch, I chose to sit at a table where I knew no one. Everyone was encouraged to do this, but I question how many people followed through. If you’re not used to stepping out of your comfort zone, you likely won’t make that first step at a conference of 1,000+ people.

CIW, in my experience anyway, while great, is all monologue (perhaps by design--perhaps it’s too large to run any differently). There were so many parts during the presentations where I wanted to jump in with my own opinions or stories. I have to imagine others felt this urge as well. It lacks in dialogue, and that’s where I see the strongest potential for growth and truly delivering a platform to "inspire, connect, and activate the city of Chicago and beyond, (and serving as) the global hub for new ideas, an ecosystem for innovation and a playground of intellectual recreation.”




Rajiv Nathan is the co-founder of Idea Lemon with a background in digital and mobile strategy. He is passionately curious, a people-meeter and lives by the motto, "you miss 100% of the shots you don't take."