This paper articulates the practices that I employ to encourage persons who might be standing on the threshold (a disorienting dilemma) of a potentially transformative process. Because their ontological security has been disrupted, they welcome a guide to accompany them as they venture into the unknown. During my fifty years as a psychotherapist and twelve as a professor, I have accrued some practical wisdom regarding that process. Theoretically, I shift the focus away from the interface between one’s meaning perspective and the circumstance that disorient to an emphasis on the internal meaning structure. There, I suggest that we are not unitary, rational creatures but rather a collection of sub-selves—each with their own premises—often competing with one another. When this occurs, something other than the person’s conscious intentions generate inadequate responses to their dilemma. I teach the individual to consciously welcome these sub-selves in order to promote overall integration. Next, I outline three methods: mapping psychological processes from intention to outcome, generating original behavioral responses, and utilizing the relationship to compensate for the above-mentioned loss of ontological security. Although these practices were developed in a therapeutic context, they implicitly inform my pedagogy as well.