Background: The outdoor industry has experienced a number of problematic issues, one of the most prominent being staffing concerns related to hiring, retention, and burnout. Purpose: This study investigated the relationship between the level of experience, gender, and age on the selected variables of resilience, coping skills, mental toughness, levels of anxiety, job positivity, and burnout. Methods: This study used an electronic self-report instrument to measure the six variables. For simplicity, level of experience was measured as the overall length of time working in the outdoor industry. Findings: Results partially supported the hypothesis that level of experience can be linked to higher job positivity, lower anxiety, and higher levels of burnout. No significant relationship was found between level of experience and resilience, mental toughness, or coping. Gender and age did not moderate the relationships between experience and the outcomes of interest. Implications: The findings of this study suggest that experience in outdoor adventure programs may be associated with higher job positivity, lower anxiety, and lower levels of burnout among more experienced staff. These results highlight the importance of providing opportunities for individuals to gain experience in order to enhance their well-being and job satisfaction within outdoor adventure programs.