In this engaging discussion, Rachel Barney, a Professor of Classics and Philosophy at the University of Toronto, dives into her academic journey and passion for ancient philosophy, particularly Plato. She shares her thoughts on the optimistic view of failure in philosophical pursuits and how setbacks can lead to growth. The conversation also reveals the surprising connections between art, philosophy, and even Monty Python, illustrating how humor can challenge societal norms and serve as a powerful teaching tool. Lastly, Rachel explores themes of fear and existential dread, enhancing our understanding of these complex emotions.