This study investigated the nature of transformative learning experiences as qualitative shifts in identity by employing a basic interpretative qualitative methodology using data from semi-structured interviews with eight participants in a re-entry job skills program, that is, with participants in a program that was designed to aid them with their re-entry into society. This study explored the nature of these learning experiences through the transformative learning theoretical framework articulated by Illeris (2014). The findings supported Illeris' conceptualization of transformation and contributed to the explication of key concepts in his theory including regressive transformative learning, and identity as situated in three dimensions of learning. Further, this study showed that, for the study participants, transformative learning as a qualitative shift in identity entailed interconnected changes in participants' ways of being in, acting in, relating to, and knowing the world. The data also helped explain learning experiences that were both transformative and negative experiences, that is, a kind of experience not countenanced by the predominant Mezirowian view of transformative learning. This study thus found that transformative learning conceptualized as a qualitative shift in identity accounts for such transformative yet purportedly negative experiences. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]