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9 Takeaways from 9 Years of Chicago Ideas


The foundational design of Chicago Ideas is in sync with these times in which we find ourselves.

When so much of the world feels uncertain or confusing, the mission of Chicago Ideas to galvanize our community by starting with what is and heading straight into what is possible through storytelling, ideas and connectivity takes on a special importance. Now more than ever, we believe this power of imagination matters.

We believe this is a time to consider the role each of us plays in creating the future. In this tenth year of Chicago Ideas, it’s time to RE. REthink, REview, REorient, REvise, REmind, REcommit — to name just a few. The South African poet Gift Gugu Mona advises: “Rethink, relearn, replan” rather than regret. Her words truly resonate in these times.

The pandemic and the resulting “zoom overload” have led us to REformat Chicago Ideas Week 2020. We’ve REvised our in-person, week-long series in today’s landscape and stretched our  programming year-round to include free virtual events. We are acting on our belief (in mid-Covid times) that connectivity is best created incrementally (rather than through big-bang productions). We embrace this evolution. We find great optimism within change.

In previous years, my nights before Chicago Ideas Week took on a mindful and contemplative tone. The last number of years I’ve had this reflection and curiosity on what I learned during the years before, what energy I got from the speakers, and where these connections might go from there. This year, I’m REenergized by the Chicago Ideas platform. Curiosity has the extraordinary power to open up optimism and opportunity, especially during hardship.

I thought I’d share some of the lessons I’ve learned over the past nine years — so I offer a far-from-complete list of Chicago Ideas Week insights:

  1. The quality of the questions asked is directly correlative with the depth and intimacy of the response. If you take the time to prepare for a conversation with someone, and do your best to do your homework on their lives and their background, you will be prepared to derive the greatest possible insight that they can offer about their journey and their cumulative wisdom. Great interviews depend on an interesting subject, but also an empathetic and curious interviewer.
  2. It pays to be intentionally, outwardly curious. My conversation with director Brian Grazer taught me about his “Curiosity Sessions” in which he intentionally reaches out to a wide variety of people with no agenda (and no “ask”) other than to get to know them and explore their passions. Grazer has been nominated for many Academy Awards (and won one for A Beautiful Mind), and the source of much of his work begins with people he meets in these Curiosity Sessions.
  3. A consistent theme of extraordinary achievers across a wide variety of fields is that they do what they do out of love (and Martine Rothblatt’s story stands out, for both her tremendous sense of love and achievement across fields). Love for being their best, love for exploring their passion, love for the journey of life. I often asked people about the “why” that drives them, and (not surprisingly) the answers are rarely money, nor are they power or fame. The pursuit that drives them is their love — love of exploring the limits of their skills and abilities, love for the fields that they are in, love for their families and for their friends, and the love they feel for themselves when they are doing their best work.
  4. Failure is a part of every great success story. Time and time again, whether talking to doctors, journalists, entrepreneurs, activists, ultra-marathoners, military leaders, or many others, the binding tie that is part of lifelong learning is the value of failure, and the reaction of these individuals to adversity. Failure is inevitable if you are putting yourself out there and testing your limits, and failure is a hurdle to be overcome on the trail of life — not a consequence that leads to an end.
  5. Excellence can be found when you are willing to take what you’ve done and then ask yourself “now where do I go from here” — when you set a high bar for a feeling of “satisfaction.” I asked the question to several people who have achieved remarkable success, “How often do you feel satisfied? How often do you reflect on what you’ve done, rather than think about what you still can do?” If I had to put a percentage on it, I’d say the consensus was 10 percent reflection on accomplishments, and 90 percent focus on what can now be done with the talents that the person has developed. I’m not saying that this is good or bad, just that it is my observation from the speakers on the various Chicago Ideas stages.
  6. Humor is an amazing way to build relationships. The more stories I heard from world leaders and military commanders, the more stories I heard about conflict that was solved through a series of conversations and compromises that in some way were facilitated by humor and a lightness of being. Even in the most intense situations, a good laugh goes a long way.
  7. We are all human — even those we hold to be icons in their fields, and especially those who are “famous.” The human condition and its limitations, and the opportunities that arise from finding basic human bonds despite these limitations, seem to be a part of every story of impact. In other words, the more we can be empathetic to others, the more effective we can be.
  8. Last year, David Lynch said onstage that for him “Ideas have always driven the boat,” which captures my feeling that it’s all about stories. We are a series of stories that are told to us, told about us, and told by us. We communicate best through stories, not rote facts. And storytelling is the art that enables progress in any and all fields — not just theater and film and other types of art, but also medicine, space exploration, social activism, criminal justice, and so much more. Doing our best to become better storytellers is an effort worth making, as it offers the tools that empower each of us to better accomplish our goals.
  9. My greatest highlight of the past nine years of Chicago Ideas? Being told about an incredible number of serendipitous relationships that have resulted from the starting exercise of each CIW event. What’s the exercise? A simple request of the audience: “Please introduce yourself to someone you don’t know!” This two-minute exercise at the beginning of each Chicago Ideas event has led to more relationships, more collaborations, and more “beginnings” than I can list in this post.

I’m reminded of one more lesson — something that has taken on new importance this year. In 2015, Dan Harris spoke at CIW about the importance of fitting in meditation in your days as a practice of mindfulness. The energy that comes from a thrilling speaker like Dan at Chicago Ideas is the same energy that comes from meditation and of the process of going from imagination to reality. Which is why, after nine years of Chicago Ideas, I’m more excited than ever to listen, ask, learn, think, and then act to put some of these ideas to work.

To learn about upcoming Chicago Ideas virtual events, visit our website.

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Brad Keywell ©2021

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