This article uses life coaching as a case study for understanding the attempts of one occupational group to define their work as a profession and themselves as professional people. Life coaches' efforts to legitimate their work are examined within the context of the economic downturn and exemplify an emerging employment trend in the American labor market: college-educated workers pursuing non-standard work as independent contractors in personalized service occupations. Using in-depth interviews with life coaches, I focus on the collective and individual strategies workers use in their attempts to carve out new occupational jurisdictions for their services and bolster their professional status. I explore how gender shapes life coaches' experiences and professionalization tactics; further, I predict that these gendered processes will ultimately influence the trajectory of the life coaching industry more generally. My findings highlight the complexity of current employment relations and offer empirical insights into the study of work, occupations, and gender.