Retiring senior military officers (SMO) are a specific group of adult learners in role transition. SMOs have the shared experience of high-level leadership roles, senior managerial experiences, and military rank. They experience some similar transition challenges as other military affiliated learners, such as military-civilian culture; however, in their military roles, these individuals are in powerful roles of command, often in high stress to include life and death combat situations. Therefore, the SMO adult learner transitioning into post-retirement, second career work experiences has important context changes to explore. Those context changes include integrated ways of moving among levels of novice to expert in organizational structure, ethos, international experience, and managing and leading in crisis. Through reciprocal learning programs, hiring organizations and SMOs have an opportunity to make headway into bridging the military-civilian divide.