In 2008, I began the process of preparing for a study that I carried out over the next 3 years to examine resiliency among Mexican and Mexican–American transsexual entertainers. My interest in the population was generated by my own lived experience of coming out in the community some 20 years prior to the study, and the fact that this was a community who were under-represented in transgender-serving clinical settings. My literature search yielded disheartening data that indicated high risks of drug abuse, depression, and exposure to sexually transmitted diseases, while there was little that portrayed strength and resiliency that came with the experiences of navigating multiple identities as Mexicans or Mexican–Americans, entertainers, transsexuals, and women. I chose a multiple case study design, using interviewing, observations, and reviewing artifacts as my data sources for work with three participants. What follows is my experience of using a personal network of people in the gay bars to identify participants, the difficulties of managing observations in bars, the role negotiation that occurred during times when interviews became emotional for participants, the experiences I had as the study developed and matured, and the practical issues that arose with compiling data for each of the separate cases.