Determining the researcher role is an important, yet challenging decision for any project. It is especially difficult for new educational researchers whose prior experiences as teachers, administrators, and students may make it challenging to disengage from participant roles. In this case, we offer an example of a research project in which we struggled to negotiate participant and nonparticipant observation roles. We describe the project and our data collection efforts including our mistakes and eventual solutions. We present the benefits and challenges of engaging in participant and nonparticipant observation, specifically for those in the field of education. Finally, this case highlights the importance of thoughtfully selecting one's role in observational data collection. [This content is provided in the format of an e-book.]