In our work with educators at every level--from preschool through university, preservice and inservice--one of our greatest challenges is that of helping them see themselves as capable of orchestrating their knowledge of their discipline with their knowledge of their students in order to make informed instructional decisions and to act on them. This proactive disposition runs counter to their own experiences in highly structured, test-and-right-answer-oriented schooling (Carmichael, 2010) which influence how they work with their own students, whether P-12 or university. For those who successfully navigate this course, the excursion (Cousin, 2006) is nothing short of transformative (Land, Cousin, Meyer and Davies, 2005). Their language about themselves and about teaching (Meyer and Land, 2005) becomes more active, confident, and authoritative as they reconstitute their identity (Land, Meyer and Baillie, 2010) as “teacher”. For many, this rite of passage is troublesome (Perkins, 1999) and very messy, especially when the more compliant, other-directed role is reinforced by social or political context. The anxiety (Cousin, 2006) attached to this new “way of thinking and practicing” (Meyer and Land, 2003, p. 9) as an educator is often most distressing for our strongest students, who have been the most successful over the years in figuring out what their teachers consider “the right answer”, and in producing it. Whether we label it a threshold concept or a threshold conception (Land et al, 2005) or something else, the disposition to see oneself as an informed decision maker, and to act on that, is a crucial one in the professional development of educators. We will share data from our own work as we have grappled with this phenomenon.