I reflect on the methodological processes underpinning a dissertation that investigated male learners' reasons for leaving high school early and the strategies they employed to negotiate everyday life. A qualitative case study was conducted with nine male early high school leavers between the ages of 18 and 25, as well as 12 stakeholders involved in the Orange Farm Township, south of Johannesburg. Purposive and snowball sampling techniques were used. Data were collected through in-depth interviews, document reviews, and observations. Narrative analysis revealed complications related to the notions of space and place of the potential participants and the researcher. In the first place, the difficulty was not in identifying participants, but in establishing rapport to the extent that they agreed to participate in the research. Assumptions about space and place gave rise to expectations that had to be managed, and consequently the researcher had to rethink the methodological choices. In particular, participants' perceived real social positions and their relation to different social spaces had to be negotiated. It is suggested that relatively novice researchers, researching male early high school leaving in familiar spaces, can mitigate complications of space, place and stigma during fieldwork by using multiple sources of data and strategic, flexible interviewing techniques.