Presently, the bulk of research and theory on the veteran population has remained narrowly focused on correlates of psychopathology associated with posttraumatic stress disorder (PTSD). To date, inadequate research has explored understanding the broader category of transitional difficulties (including intercultural interactions, individual cultural identity, societal cultural values, social support loss, and cultural language fluency) and possible heterogeneity of outcome variables associated with both PTSD and acculturative stress. In this paper, I attempt to address this deficit by blending qualitative thematic analysis with first-person reflections associated with acculturation and acculturative stress. This approach is intended to offer the reader a contextually rich understanding of concepts that may be new, unfamiliar, or vague. Thematic analysis examines three aspects of acculturative stress impacting the lives of military veterans when returning back to civilian society: military and civilian cultural differences, perceptions of being stereotyped due to their differences, and adopting a new self-identity. Personal reflections on identical aspects of acculturative stress, draw upon my firsthand experiences going through the acculturation process between military and civilian societies. The conclusion offers implications based on this new understanding, which includes future lines of research needed to further our understanding and support of this community.