Background: The short-term impacts of outdoor orientation programs (OOPs) have been documented in the literature for close to 40 years. While there is a fair amount of research examining the immediate effects of OOPs, there are relatively few studies exploring long-term impacts. Purpose: This study examined the important longitudinal "lessons learned" from participating in an OOP. Methodology/Approach: This study utilized a retrospective qualitative approach and employed the Most Significant Change technique to understand meaningful lessons learned. Alumni from an OOP participated in semi-structured interviews. Thematic analyses included open coding, focused coding, and axial coding. Findings/Conclusions: Primary themes that emerged from the coding process included community and social connections, mental health and well-being and environmental appreciation and value of nature. Participants reported learning valuable lessons related to community building, coping, stress relief, resiliency and thriving, and connection with nature. Implications: Results provide evidence supporting positive long-term effects of OOPs. A particular highlight is how participants noted the OOP helped shape their "favourite self" years after their university experience. Researchers and practitioners can use these results to inform OOP curricula and to include in program marketing and lobbying efforts.