Uncomfortable Conversations and How to Have Them

The year’s first McCloskey Speaker sets the tone for the exchange of ideas.
On a recent Sunday, students, faculty, and School guests settled into the comfortable seating of of the Milligan Center to learn about how and why they might make themselves uncomfortable.

The event was a talk by Zachary R. Wood, the first in this year’s McCloskey Speakers Series. Mr. Wood, known for his dynamic perspective on free speech, race, and dissenting opinions, is the former president of the group Uncomfortable Learning and a recent graduate of Williams College. Mr. Wood is currently a columnist and assistant opinion editor at The Guardian and a Robert L. Bartley Fellow at The Wall Street Journal. His recent work has appeared in The New York Times, The Wall Street Journal, The Washington Post, The Huffington Post, The Nation, The Weekly Standard, Times Higher Education, and Inside Higher Ed.

In his talk, Mr. Wood shared some of the personal history that led him to embrace and champion uncomfortable conversations. He also described his guidelines for conducting constructive dialogue with people holding opposing viewpoints. The talk concluded with a dynamic question and answer period, which highlighted how much the talk resonated with the students. After joining the School’s Formal Dinner directly following his lecture, Mr. Wood continued the conversation with students in the Thacher Room.  

“I really enjoyed the lecture,” said junior Mike Sanderson. “My favorite part of Mr. Wood's message is the necessity to understand all points of view to make the best decisions for yourself. It truly encourages intellectual and political independence.”

The next day, Mr. Wood spent some time with the juniors the U.S. Honors History class taught by Whitney Livermore CdeP 2004. “He kept them at the table and wanting to know more about his ideas,” said Whitney, “even as some of those ideas may have been hard for us to grapple with. I came away with a renewed sense of commitment to pushing myself to seek out different perspectives, as well as an even higher sense of respect and pride for our students, who had truly maximized this opportunity to probe deeply their own ways of thinking and learning.”

Junior Tea Wallmark emerged from class with a sense of optimism. “I truly enjoyed Mr. Wood’s visit to our class because it showed me that change is possible. His passion and dedication towards spreading uncomfortable learning to young students gave me hope that we can still strive to find unity and understanding in this divided country.”

Mr. Wood also sat down for a conversation with two Thacher seniors and you can read their interview here
“Our goal with this first McCloskey Speaker of the year was to invite the community to consider what we have to learn about ourselves, our world, our values, and our responsibility as citizens by engaging with those whose viewpoints differ greatly from our own,” explained Head of School Blossom Pidduck. “If we protect ourselves from difficult conversations, from uncomfortable realities, from the challenge of solving complex problems, how can we thrive in a diverse and often divided world? How can we build authentic community? How can we do good where it is needed most? Our work is to reach beyond what we know and are comfortable with, to see the world through the eyes of those wholly different from ourselves, to listen carefully and critically, and to engage for the greatest good. It’s my hope that this year’s McCloskey speakers will help us do just that.”

Later this year, the McCloskey Speakers Series will risk some potential discomfort by bringing other speakers to campus to share their perspectives, some of which are likely to provoke disagreement. Before and after these lectures, which have yet to be announced, time will be set aside in and out of class to provide Thacher students with context for grappling with the ideas these speakers will bring and to encourage deep listening and critical discernment.

The McCloskey Speaker Series aims to bring high caliber, inspirational resources and speakers with a wide degree of expertise and interests to Thacher and to the Ojai community at large. It was made possible by a 2016 donation from the McCloskey Family Charitable Foundation that supports the operational costs of the series in perpetuity at Thacher. Previous McCloskey speakers include Dr. William “Bill” R. Cook, medieval scholar and lecturer, and Troy Carter, talent manager and founder/CEO of Atom Factory.

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