Worldwide schools are confronted with a myriad of contextual challenges such as teenage pregnancy, HIV and AIDS, poverty, substance abuse, child headed households, suicide, to mention a few. South Africa, a country that is yet to win the war against poverty and underdevelopment is not an exception. Life Orientation (LO) as a subject presents schools in South Africa with opportunities to empower young people with knowledge and life skills to make meaningful choices. Whist the Department of Basic Education in South Africa has developed a clearly set LO curriculum, which has well-defined outcomes; it is not clear whether their training as LO teachers adequately equips them to deal with these multiple social issues affecting learners. The focus of this phenomenological study was to explore the dynamics in the Personal and Professional Development (PPD) of LO teachers in South Africa, in the Gauteng Province. Data were collected through nine individual interviews, two focus group interviews and two collages by participants from 14 districts within the Gauteng Department of Education (GDE). The findings suggested that the PPD of LO teachers was impeded by the fact that it did not address issues such as their personal experiences, their attitudes towards LO, the LO curriculum delivery, and the complex roles they play in dealing with challenging issues. Based on these findings recommendations are made on how to best address these dynamics through their PPD and how to best support LO teachers to ensure meaningful teaching of LO.