After devoting over 35 years to my career in accounting I began to develop some health issues. I started to fantasize about what I would do if I left my nine to five job, a possibility would be to develop a career in selling my art. I had always considered myself to be an artist, so perhaps it was time to take the plunge and begin actively marketing my work via the Art Fair circuit. Through the years I had been accumulating and storing quite a few of my paintings and had gone to the expense of having some of the better paintings reproduced, all with the impetus of ultimately entering into art sales. I subsequently decided to quit my high stress job in accounting and sold my condo in Martinez, CA. and moved into a lovely home in the North State of California, with a wonderful view of Mt. Lassen. I hoped the transition to the country would provide a more conducive setting in which to create art. I also purchased a Ford Van conversion and a small hauling trailer, in order to begin this new phase of my life. I imagined what a relief it would be to celebrate life with other artists and share my paintings via exhibits and shows throughout California and perhaps even the Southwest, who knows, anything seemed possible with my new and exciting plans. My book, in diary format, encapsulates my adventures in participating in outdoor art shows over the course of several years. I learned many lessons about myself and human nature in general, as I attempted to change from my rather taciturn accounting personality to embrace a more out going sales persona but as they say, "a leopard doesn't change its spots" and frankly neither did I. However, I remained motivated to evolve into an Art Show Gypsy. I sashayed from show to show, hauling my little trailer filled with all the accessories required to set up a show on a street or in a park; the canopy, stands, etc. Being on the street, exposed to the elements of nature, was more challenging than I anticipated but it still felt good to be free of walls and structure. I hope that by sharing my stories about the shows I participated in will help other artists decide whether to take the plunge into a whole new world of being an "Art Show Gypsy."