In this narrative inquiry study, we interviewed 5 graduate assistants who served as the primary point of contact for their public university’s lesbian, gay, bisexual, and transgender (LGBT) student services. We were interested in understanding the structural challenges that affected these employees’ experiences in their roles. Participants were interviewed 3 times over 1 academic year to better understand their job roles and expectations in-depth. From the data, 1 major theme experienced across the participants was a feeling of being set up to fail within their positions. The participants also discussed 4 subthemes that focused on external structural challenges; these included (a) the institutional geography of the LGBT center; (b) inconsistent supervisor support and content knowledge; (c) lack of formal training and professional development; and (d) limited resources of time and money.