In this presentation, two junior IT staff members will share their journey of learning and implementing advanced endpoint management systems, specifically JAMF Pro and Microsoft Intune, within a resource-constrained higher education environment. We will provide a look at our experiences, from initially being overwhelmed to growing competence, highlighting the unique challenges we faced and the strategies we developed to overcome them. We will delve into our process of self-directed learning and team knowledge transfer. We will highlight the mistakes we made and what we learned from them, along with the small victories that kept us motivated. We will continue with a discussion with attendees to create a supportive space for professionals at all levels to share experiences, brainstorm solutions, and develop strategies for success in endpoint management. Whether you are new to the field, facing similar resource constraints, or an experienced professional looking to mentor others, our discussions will focus on providing insights and practical takeaways for navigating endpoint management.