The six authors of this commentary series, who have recently transitioned into or within an academic career, discuss challenging aspects of an academic career change. This is a three-part commentary series that explores select challenges: 1) feedback, evaluation, and advancement; 2) understanding and balancing of distribution of effort; 3) learning how and when to say yes. Faculty, or those interested in pursuing a career in pharmacy academia, can refer to this commentary series as a reference. Schools of pharmacy may utilize this as a tool for new faculty members during orientation in order to ensure smooth integration into the academic environment.