The demand for higher education has been increasing in Jamaica as in many other Caribbean countries. Those who respond to such demands, pursuing further studies in higher education, will need to navigate many obligations and challenges. Additionally, some individuals may be First Generation (FG) adult learners and may lack the tacit knowledge and emotional sustenance to help them succeed. Consequently, adult learners pursuing postgraduate studies will need support in understanding themselves as learners and how to succeed. This study reports findings on challenges that non-traditional adult learners in a Jamaican higher education context face in pursuing postgraduate studies. Using the photovoice research method, qualitative data were collected from 10 adult learners through photographed representations of prompts, photovoice focus group discussions, and participants' reflections. The main findings revealed that the adult learners experienced multiple conflicting emotions as they engaged in their postgraduate programmes of study; experienced challenges balancing their multiple roles and responsibilities, some of which were linked to their status as FG adult learners; and characterised the COVID-19 pandemic as having a dualistic nature, one that exacerbated challenges whilst also offering them opportunities to focus on their studies as well as themselves. The article makes recommendations for supporting these adult learners at the institutional and personal levels as they pursue their studies.