Abstract: Objective: The authors of the present study assessed changes to veterans’ perceptions of well-being following participation in a military-to-civilian transition program, Flourishing Through Life Transitions (Flourishing), a two-week residential program designed to address well-being and career development for veterans transitioning from uniformed service. Method: We administered assessments at baseline, upon program completion, and collected follow-up data at 6 wk and 6-months post completion. Among the 32 individuals enrolled in Flourishing, 22 participants completed the daily diary portion of the study, while 13 completed the follow-up repeated-measures assessments. Results: Pilot data demonstrated statistically significant improvement in strengths self-efficacy and satisfaction with life. Scores for social connectedness, meaning in life, and stress also improved, but were not statistically significant. Results of the daily diary demonstrated positive trends in hope, well-being, and mindfulness. Conclusion: Preliminary findings from this pilot study suggest the potential utility of Flourishing, providing feasibility for larger trails to confirm the results.