Jim served as Artistic Director of Redmoon Theater from 1992 to 2009. As artistic director he created numerous original theater and spectacle events ranging from massive public celebrations to formal indoor shows. Originally co-artistic director with founder Blair Thomas, Jim became sole artistic director in 1998 and has been a principal voice in over 30 productions in this capacity. Most recently, Jim created The Princess Club, an exploration of gender, fantasy, and beauty. He also created Redmoon's large scale spectacle Twilight Orchard in Columbus Park on Chicago's West Side, attracting 7,500 audience members over seven evenings.
Jim's other productions include The Golden Truffle, a dessert musical, and Galway's Shadow, which converted the facade of Chicago's Museum of Contemporary Art into a giant shadow screen. The All Hallow's Eve Ritual Celebration, which he conceived and directed, attracted tens of thousands of people to Logan Square for an evening of community spectacle from 1998 to 2002. He also collaborated on a large scale, site-specific spectacle with an international team in Tasmania, Australia entitled Dream Masons, which opened in March 2007.
Jim designed the Family Center at the Spertus Institute in Chicago. Jim's work has been commissioned by Chicago's Field Museum, the City of Chicago's Department of Cultural Affairs, the Mayor's Office of Special Events, the Pritzker family, and the Zell family.
Jim is a recipient of numerous Jeff citations, an Award for Excellence in Puppetry Arts from the International Puppetry Guild, and he was named an "artist to watch for the next decade" by The Chicago Tribune. He completed his course work for a PhD in Theatre and Drama at Northwestern University, but dodged his dissertation and took a Master's degree instead.
Called "one of Chicago's most creative individuals" by City of Chicago's cultural affairs commissioner Lois Weisberg, in July 2009 he was named Chicago's first-ever artist in residence.