Facilitating groups in outdoor education can sometimes be very challenging, and self-doubt and the fear of facilitating inadequately add to difficulties that facilitators must sometimes manage. In this paper, I will explore some of the ways by which facilitators contribute to the difficulties they experience and, furthermore, to explore some solutions. Negative self-talk can sabotage our best intentions as facilitators, by reducing the levels of free attention that are needed to facilitate well. I draw on the findings of a naturalistic inquiry conducted with 7 facilitator educators and 104 graduates of facilitator education programmes. Data collected through semi-structured interviews, participant observation and qualitative surveys were analysed using the constant comparison method. Based on my research findings, I contend that outdoor education programmes do not need perfect facilitators. Rather, facilitators who can be authentic, self-aware and fully present for their groups will improve outdoor education programs.