Data on enrollment in healthcare occupational training in programs such as the Health Profession Opportunity Grants (HPOG) Program are available at both the local program level and nationally. Summarizing "which" trainings participants choose is straightforward, but why they make those choices is not well understood. This second brief in the HPOG 2.0 Participant Perspectives series considers why HPOG 2.0 participants chose the healthcare field in general, and why they chose their specific healthcare occupation. Because job quality was a clear consideration for the participants we interviewed, the brief also provides further detail on their understanding of job quality within the healthcare field. This paper also offers perspective on how interviewees thought broadly about what De Vos, Akkermans, and Van der Heijden (2019) term "crafting" a career--an ongoing, dynamic process of fitting together family financial needs, work experience, and opportunities for additional training. Finally, it offers some policy implications, particularly for the structure of career pathways program design and employer engagement. The brief draws on data from 153 in-person interviews with participants in career pathways programs funded by the HPOG Program. [For Brief 1, see ED621587.]