Trinidad and Tobago is a developing country which is challenged with the issues of poverty, human development, and the sustainability of that development to some degree. Over the years, governments have implemented numerous programs to address poverty and improve sustainability among the most vulnerable sections of society. I chose single mothers because they are one of the most vulnerable groups, and they also have unique challenges in balancing social and economic life with parenthood. I was curious with respect to why this particular group is not achieving what it is hoped they would achieve. For example, why wasn’t there a significant shift in the employment rate for single mothers? Why weren’t single mothers starting small businesses? Why was this family type still at risk? I was very interested in the socio-economic impact of skills training on poor single mothers in rural Trinidad, and there were no previous studies examining the circumstances of single mothers in Trinidad and Tobago. My research sought to document the relationship between single mothers, poverty, employment, and learning a vocational skill such as tailoring, floral decoration, tiling, or plumbing. I attempted to highlight some of the issues faced by single mothers who were educating themselves through some of these government programs while raising a family in a rural community. The study was qualitative in nature and should help the reader understand some research challenges which arose in interviewing, planning, and executing the research and how to work through these challenges as best as possible.