Revision with unchanged content. Self-employment has taken the centre stage in the Canadian economy. In Canada, in the 1990s, 75% of new jobs were created through self-employment. Studies have tried to understand this trend using aggregate data, with limitations. This book also asks the question of why self-employment? using qualitative data. This book began as a Masters’ thesis presented to the anthropology department at Concordia University in Montreal. It remains in its original format. The author explored why two web designers reject the notion of working for a corporation and choose self-employment. This book should be read by anyone interested in understanding the anthropology of work, self-employment, self-identity and creativity. As a student the author was encouraged by her university professors to study in her own backyard, and it is the hope that anthropological students may read this book and be themselves inspired to do the same.