Health professions are ranked among the most stressful occupations and have a much higher likelihood of absenteeism from work. In this article, we present findings from four health professional case studies in our Healthy Professional Worker partnership, involving surveys with 1,860 respondents and 163 interviews with nurses, physicians, midwives, and dentists conducted between December 2020 and April 2021. We found that the pathway from mental health experiences through to the decision to take a leave of absence and return to work differed between the health professions and that both gender and leadership matter greatly. There is a need to de-stigmatize mental health issues and encourage greater awareness and support from supervisors and colleagues. Leadership can play an important role in mitigating mental health issues, and as such investment in both leadership training and mentorship are important first steps in acting upon our research findings.