This article explores some of the challenges and benefits of doing a dissertation with participants from a population to which I belong and on a topic some consider controversial, that of gay and lesbian educators. I describe the homophobia I experienced and how that homophobia affected my choice of topic, the research process, and my job prospects. Each step of this research journey presented me with a variety of delicate decisions. I discuss my thought processes in resolving these dilemmas and some of the practical solutions I used to address a variety of difficulties. Although written specifically about doing research with gay and lesbian teachers, many of the lessons I learned throughout this process can be applied to a range of research situations. For example, many researchers share cultural backgrounds with their participants. This presents both the opportunity to establish rapport with participants quickly but also the danger of the researcher reading his or her own experiences into the data. I describe some of the ways I addressed this issue as well as others commonly faced by those doing dissertations. I conclude that doing a dissertation on a topic I feel passionately about sustained me throughout the dissertation process.