In this episode, we talk with Stu Gray, associate professor of politics at Washington and Lee University, whose winding journey from West Point to political theory is a story of risk, reflection and relentless curiosity. Gray shares how his fascination with both Western and Eastern traditions reshaped his understanding of identity, meaning and what it truly means to live a good life. We explore the philosophy behind his popular courses, including one inspired by “Black Mirror,” and how he invites students to unplug, look inward and critically examine the role technology plays in shaping modern identity. From the allure of “becoming” over “being” to the quiet power of awe, this conversation delves into questions that linger long after the classroom. Whether you're interested in politics, philosophy or simply navigating a digital world more mindfully, this episode will leave you thinking deeply and seeing differently.

In this episode, Will Dudley, Washington and Lee University president and philosophy professor, shares how a lifelong love of asking questions shaped his path from an aspiring mathematician to a college president. As an educator at heart, President Dudley elects to teach one philosophy course a year, which explores the university’s mission statement. He talks of how remaining in the classroom grounds him and positively influences his role as president as he invites discussions on honor, integrity and civil discourse. From the value of freedom of expression to the joy of fly-fishing with students, our conversation invites you to reflect on the enduring impact of a liberal arts education and how to keep your mind an interesting place to live.

In this episode, we talk with Jay Margalus, Johnson Professor of Entrepreneurship and Leadership and Director of the Connolly Center for Entrepreneurship at W&L. Margalus shares his unconventional path from law to software to academia, and why he believes embracing risk is essential, not just for entrepreneurs, but for anyone seeking a meaningful life. We explore how he's helping students unlearn rigid, test-driven thinking and rediscover creativity through play, uncertainty, and real-world experimentation. From the philosophy behind W&L’s entrepreneurship programs to the hands-on work happening at the Connolly Center, this episode is packed with insight into what it means to take smart risks, build boldly, and avoid the quiet danger of regret. Whether you're an aspiring entrepreneur, educator, or just rethinking your next move, this conversation will inspire you to take the leap.