Devastations, transitions, crises, and challenges can trigger what are sometimes referred to, particularly in the field of adult education, as "disorienting dilemmas." Jack Mezirow, an adult educator and social activist, maintained that a disorienting dilemma occurs when an individual encounters a life challenge that cannot be resolved by his or her previous frame of reference. Today, people are facing increasing numbers of personal, societal, and global challenges. Therefore, it is extremely important that resolutions to countless life challenges are researched and viable resolutions are found. This basic interpretive and descriptive qualitative study examined participants' approaches to resolving crucial life events which are considered disorienting dilemmas. Additionally, this study determined if the 10 phases of Mezirow's transformative learning theory were utilized in negotiating the dilemmas. Data were collected through face-to-face interviews with 14 participants. Purposeful sampling was employed in order to obtain cases that could give most insight into the approaches that were utilized in the resolution of the disorienting dilemmas Semi-structured questions were employed. Findings from the study revealed that factors such as (a) the acceptance of the dilemma, (b) the nature of the dilemma, and (c) an array of emotions, played important roles in changing or not changing perspectives and negotiating disorienting dilemmas. Findings also revealed that no transformations were sudden or immediate. Participants took from a month to six years to begin the process of resolving their dilemmas. Of importance is that most transformations were "modified" transformation and not total transformation as the participants continued to maintain many of their preconceived notions. It was also found that all participants utilized some of the 10 phases of Mezirow's transformative learning theory in negotiating the dilemmas, but all did not transform. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]