Do you ever look back on decisions you made, and wonder, “What was I thinking?” Hindsight can be 20/20, particularly after a major transition such as starting a new leadership position. This brief talk will explore one new director’s experience in her first four semesters as director of a small academic library, including mistakes made that helped lead to lessons learned. Topics include preparing for the transition, relationships with supervisors, setting team expectations, and communicating with staff. Participants can expect to learn from someone else’s mistakes, and take away real-world, applicable advice that can potentially save them from making the same types of mistakes.