A disorienting dilemma is related to a sense of loss of balance or normalcy complicated by a problem that seemingly has an unsatisfactory solution. According to Mezirow (1998), disorienting dilemmas are also connected to events that have been set into motion, causing a learner to engage in self-examination resulting from feelings emanating from an experience. This article presents the author's reflections on her disorienting dilemmas and discusses how her disorienting dilemmas have helped to shape and inform her philosophical belief and practice as an adult educator. The author concurs with Merriam (2004) who notes that it is because of these moments, learning can be transformative, ultimately leading one towards mature, autonomous and developed thinking. Here, the author shares two memories that are illustrative of what she struggled with as she worked to understand her new life as an adoptive parent of a twelve-year-old adolescent child.