In this paper we examine the effect an outdoor and experiential education program on the life effectiveness skills of its participants. A private boys school in Melbourne focused on the challenging time of year nine to implement a program they hoped would enable the boys to develop life effectiveness skills in the areas of time management, social competence, achievement motivation, intellectual flexibility, task leadership, emotional control, active initiative and self-confidence. The program involved a progression through a variety of curriculum areas including a number of outdoor education components and trips. We specifically considered two major areas of the program. The first, an examination of the boy's life effectiveness skills after the program; and secondly whether participation in the outdoor education component had a more significant impact on life effectiveness skills compared to the other programs. Results showed the life effectiveness skills of the boys increased after each aspect of the program, with a significant difference found between the life effectiveness skills of the boys who participated in two outdoor education programs compared to only one.