For many artists, the path to financial stability while pursuing creative passions is often winding and steep. Drawing from her rich experiences as a poet, professor and public intellectual, Carl’s guest Caroline Randall Williams offers unique insights into the subtle dynamics between education, wealth and social standing. She also shares her personal path to carving out space for creative fulfillment in a demanding professional environment.

This conversation also reveals a valuable lesson about the relativity of wealth perception. Caroline has existed on both ends of the wealth spectrum, from working as a teacher in rural Mississippi, to attending boarding school with students who had access to vast amounts of money and privilege. She candidly shares her experiences from both perspectives, as well as addresses the age-old question: Who’s the more important artist? Shakespeare or Lil Wayne?