This project explores the micro-processes of identity construction within the emerging profession of coaching, whose members are predominately self-employed. While efforts have been made to survey the coaching industry in order to paint the “big picture” (see AMA, 2008; ICF 2008, 2012a, 2012b; Sherpa Coaching, 2008), the intent of this research is to examine the diverse experiences of the individuals who perform this work, using qualitative/ethnographic methods and analyzing data from fieldwork carried out between 2007-2011. This study speaks directly to practical issues expressed by the ICF (2008), particularly regarding the preparation of and resources available to new coaches, and the long-term sustainability of the profession. The findings suggest that the institutional support for individual coaches is uneven, depending on a number of factors—one being the chosen coaching specialization. As well, several of the profession's resources, tools, and practices for identity construction can actually be the source of new conflicts, contradictions, and challenges, which in turn produce anxiety and demand more intense identity working efforts from the individual coach. Consequently, some coaches are struggling more than others and would benefit from added assistance from the professional community to develop their coaching practices. This project's ultimate aim is for its findings to be instrumental in creating new and shaping existing policy and regulation, and to alert key players within the coaching community to possible opportunities, concerns, and areas for future investigation.