This paper grapples with methodological issues related to ongoing debates on positionality and reflexivity by drawing on the author's experience of conducting research in a culturally familiar field. The paper is based on in-depth qualitative research that examined the lived realities of unemployed young people residing in the township of Daveyton in South Africa's Gauteng Province. This paper aims to transcend conventional perspectives on 'outsider-insider' dynamics as these do not fully explain the complexity of conducting research in a familiar field. The research involved the use of one-on-one interviews and group discussions. I use the term "politics of conducting research in a familiar field" to explain the texture, language, and daily realities of Daveyton, which are familiar to me given my upbringing in a similar community that I grew up in. To elaborate on this, I formulate three dimensions of the politics of researching a familiar field which are as follows: (1) Ambiguities of the 'element of surprise'; (2) Re-negotiating entry; and (3) wider concept of the researcher as 'outsider'. The paper concludes by calling on researchers conducting studies within their own or similar communities to pay specific attention to the nuances of class privilege, exclusion, and power in order to provide meaningful analysis of the existential conditions that participants face.