This article illustrates the potential of drawing as a creative method to document and analyse the shifting insider-outsider status of the researcher during fieldwork. I draw on my experiences conducting field-based research at night around outsourced call centres in Mumbai, India, where I examined how women made decisions regarding night-time urban mobility and household social reproduction. While conducting research, I analysed my fluctuating position as an insider or outsider, and how these shifts impacted research dynamics. Furthermore, I relied on boundary-making to alter my relative distance from research participants, thus shaping my positioning on the insider-outsider spectrum. I used hand drawing as a representational technique to document the site, as well as to analyse my positionality within it. This article places feminist methodological insights in conversation with geographic scholarship on drawing to make the following contributions. I show how drawing as a technique can enrich feminist claims about the complex relations between researcher and research participants, challenging a static and dichotomous framing of the researcher as insider or outsider. I also contend that feminist concerns about power dynamics can shape the use of drawing as a critical methodological tool.