While in Chicago, Simon participated in oil painting workshops in the evenings but still did not consider an art career. Still searching for his calling, Simon chose to pursue an MBA in international business during which he studied in Paris, New York, Tokyo, and nine other cities throughout Eastern Europe and Asia. At this point, his travels had brought him to over thirty countries as the cultural exposure continued to fuel the latent artist.
After receiving his MBA, Simon accepted a consulting assignment in Paris. Here he could explore the art world, which so intrigued him. In his free time, he visited art museums and painted in his studio apartment in the famous artist's quarter of Montmartre. Upon completing the Paris assignment, it became clear to him that the artist within must be acknowledged.
It was then that Simon made the decision to pursue his real passion. In 1994, at age twenty-nine, he moved to California to start his art career. He has since published five art books of his work.