Dialogical Self Theory has contributed to the endeavors to map and grid self-identity work in transition from military to civilian life throughout an empirical and longitudinal research project which focuses on existential dimensions. This article is based on a case study from this project and centers upon Sergeant Jonas, who, upon his return from deployment in Afghanistan, struggled with his transition as a new existential position was vocalized throughout the following annual interviews. This voice narrated feelings of meaninglessness, emptiness, and of having been deceived. In turn, this existential voice required an answer to a question which apparently had no answer. The meaning-making eventually evolved into an acceptance which enabled Jonas to proceed with his life. Dialogical processes between positions are important in order to go on with life amid existential concerns in the aftermath of military service since dialogicality of the self opens up a complex of dynamics of meaning-making processes, negotiations, and transformations. Based on the findings, it is suggested that the Personal Position Repertoire could potentially be strengthened by the addition of an internal existential position to its standard repertoire, at least when working with military personnel and/or veterans.