What does it mean to grow up? Why is it important? How does one measure it, and what factors make it so difficult to realize? This paper explores how one's experience in an outdoor adventure education program may be observed, understood, and potentially maximized through the lens of Robert Kegan's constructive-developmental theory. This paper shares the theoretical foundation of constructive-developmental theory and related literature relevant to understanding how a program participant makes meaning of their outdoor adventure experience. The constructive-developmental perspective can help inform understanding of participant experiences of change and may direct practices underpinning outdoor adventure programming. Kegan's theory may provide cogent understandings of change, how it is facilitated and measured, and insight as to why some youth thrive and others struggle in outdoor adventure programs.