Establishing a clinical education track as part of a radiology residency is essential in shaping future radiology educators. Many obstacles will be encountered while starting, maintaining, and improving these educational pathways. Hurdles may include recruiting suitable residents for the track, recruiting and supporting faculty advisors, sustaining long-term resident engagement, counteracting educational exclusivity, and providing adequate time and financial support. Although every program and institution may face individualized "mountains" to overcome, they are not insurmountable. The goal of this review is to address different conflicts we have encountered while maintaining the clinical education tract at our institution and to provide tips for overcoming them.