An essay on personal and collective responsibility amid shifting economic sands and elusive safety nets, focusing on one of Los Angeles' great economic engines: creativity.  Aerialists, singers, musicians, visual artists, science fiction writers, film directors, and special effects specialists are herein represented in the quest for a healthy professional life. Woven through the stories of these small business owners and entrepreneurs is the history of California's contributions to the development of health insurance in the US. Risk comes in many forms; managing it demands many strategies. Are freelance artists the coal mine canaries for a large portion of our economy? Embrace the uncertain, accept the pain, and pick up some ideas about what to wear to the upcoming semi-formal economy.