Self-identity work appears to be a challenge for many service members as they transition and reintegrate into civilian life. When other cultural influences seem to threaten an established self as it labors with transition, tension and conflict may arise and can potentially impact mental health. Insights from an ongoing longitudinal project on the subject matter indicate that an analysis of an individual, which utilizes the concept of I-positions may serve as a useful analytical tool during these processes. A longitudinal methodology combining a narrative approach with such an exploration of I-positions derived from a dialogical self framework may prove to be a promising avenue to advance the understanding of selves in transition beyond the dichotomy of the military and civilian spheres. The bridging capacity of I-positions lies partly in the capacity of significant others to link the self to both spheres and to help fill the perceived void between these two realms, which in reality may be overlapping and intertwined. The findings suggest, facilitated by two case study examples, that military transition to civilian life may benefit from a dialogical approach. This dialogical mind-set could even already be introduced and established during basic training. However, there is also a shared responsibility for individuals in civilian contexts to invite former service members into open dialogue just as the service members themselves shall strive to initiate earnest dialogue. Future research is encouraged to widen the methodology and knowledge of selves in transition.