Managing a busy clinical practice while promoting through military and academic ranks is one of the most challenging aspects of a career as a military surgeon. When retirement and transition out of the military can occur in the prime of a surgeon’s career, leadership roles can be acquired early in an attending’s career. With proper planning, a military surgeon can find time to complete professional military education, operational experiences, and academic or leadership career progression that also pertain to advancement to higher ranks. There are strategic, operational, clinical, and academic pathways to seek further leadership opportunities that can be tailored to one’s goals, skills, and interests. This chapter serves as a guide to show the various pathways, timelines, and recommended steps for those interested in advancing their careers in the military and beyond.