How Free Intelligent Conversation Helped Me Break Out of My Shell

Cliff Allen
Free Intelligent Conversation
4 min readJan 15, 2019

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It’s not often that you form life long friends in elementary school, but I was blessed to gain a few from my time there. One of those friends is Kyle Emile. Having known Kyle for so long, one thing that has remained consistent over the years is that he has a very unconventional way of thinking. So, in 2013 when he asked me to travel to Chicago with him, hold up signs, and talk to strangers, I wasn’t too surprised that this seemingly unbelievable idea was coming from him.

Me & Kyle with our JV basketball team

Now, one thing that you should know about me is that my natural disposition is that of an introvert. I would much rather explore adventures in my mind from a book than in real life. Yet, despite this reservation, I have always held a keen affinity towards the close friends that I have. So, though Kyle’s proposition terrified me, I decided to give it a shot.

Fast-forward to a few weeks later and I found myself walking down Michigan Avenue holding a sign with the words “Free Intelligent Conversation” on it. To be honest, my initial thoughts were filled with self-doubt and fear of the unknown. What if I sounded like an idiot? What if everyone was rude? What if I just stood outside for 2 hours without talking to anyone? While I was thinking these thoughts to myself a woman runs right up to me and says “abortion, go!” At that moment everything else in my mind unrelated to that question faded away, and before I knew it, I was invested in a conversation about planned parent hood and its variety of services with a group of moms on a girls’ trip!

Group with whom I had my first FreeIC conversation

From there, my own Free Intelligent Conversation (FreeIC) experience has continued to grow one interesting conversation at a time. I’ve discussed U.S. History and Middle Eastern affairs with a student from Cairo, learned about a theory that Reptilians run the country from a native Chicagoan, spoken with cops about their perspective on what it takes to protect society, and so many other amazing and intriguing conversations! Each FreeIC outing brings its own unique experience, and leaves a lasting impression on those involved, regardless of how long the conversation was.

A taste of some of my favorite outings

From this impression and the myriad of experiences gained from my conversations, I have grown and gained a new ability to engage with new people in new places. Each time, reducing the sense of “other” that often accompanies new people and new environments.

One of many amazing interpersonal conversations

This personal growth and investment in interpersonal connection with others has been at the heart of every FreeIC outing, and is the life force that causes FreeIC to continue to grow more and more after each outing.

Since the first outing back in 2012, the movement has continued to expand and touch others’ lives. From outings in cities like Chicago, San Francisco and Washington D.C., to outings outside of the U.S. in places like Sydney and Paris, FreeIC has crossed cultural barriers and lands, while motivating thousands to set aside their mistrust and invest in connecting with others. If this all sounds too good to be true, I invite you to find your local outing and try it for yourself.

Free Intelligent Conversation is a non-profit organization that facilitates engaging conversations in public places. Learn more at www.freeic.org

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