This cross-sectional retrospective study examined the life significance of participation in an Outward Bound (OB) wilderness expedition up to 50 years later to discover what participants learned, if their opinion about the experience had changed, whether the experience played a significant role in their lives subsequently, and its relative importance in comparison to other life experiences. Respondents (n = 180) completed at least one OB expedition between 1967-2017; therefore, data represented 46 of the 50 years under investigation. Over 90% of respondents indicated that their OB course(s) had made a positive difference in their lives. Emergent themes indicated that their OB course: a) promoted greater confidence and courage, b) provided lessons and skills that were transferred to other life contexts, c) increased their self and social awareness, and d) helped them develop teamwork skills. These findings enhance our understanding of the long-term impact of OB and OB-type expeditions and support the notion that significant experiences are often used as reference points in a person's life story.