Like many artists, Billyo O'Donnell struggled with the decision to pursue art as a vocation. But standing in his boss's office at a Missouri saw mill, Billyo came to a life changing realization. He saw that there are no safe paths, and decided he might as well take his own chances. So he carved his own path in the world of corporate illustration, negotiating a brilliant deal with his employer that got his paintings into corporate collections across the U.S. After being rejected from multiple galleries in his home state of Missouri, a painting trip to California inspired Billyo to start his own painting ventures. We talk about the uncertainty and dedication in multi-year projects, how the NEA contacted Billyo and expanded on his project, plus the book that followed: “Painting Missouri.” We also talk about the plein-air events and what Billyo looks for when judging painting competitions plus how he sees the art world changing in the next few years.