When the author thinks back to all the wilderness educational expeditions he has led, one thing sticks out in his mind: While he knows these were amazing experiences for the students (primarily university undergraduates), could he have done more to help them transition into the experience and out again afterwards? The author has continued to contemplate transference during three expeditions to Haida Gwaii (the Queen Charlotte Islands), one on the Stikine River and another in the Antarctic. All of these subsequent expeditions were run as field courses at the University of Northern British Columbia. In this article, the author tries to draw out theory as well as examples and lessons from practice that he feels are potentially valuable in re-shaping the way educators/instructors/mentors conceptualize transition and transference in their programs in the future. (Contains 2 figures.)