Gender influences how researchers engage with the field (Porter & Schänzel, 2018). Departing from this proposition, this chapter offers reflections on gender from masculine vantages in the context of a qualitative research project investigating tourism enterprising in southern Sweden. Tourism enterprising is an important aspect of tourism development. Focusing on personal experiences associated with family relocation to, and involvement in, the research process, the chapter focuses on the emergence of masculinities of husband-hood and fatherhood at the intersection of family and field. Exploring the processes of family relocation, site selection and apprehension, the chapter shows how masculinities of father-hood and husband-hood influence research processes in the field as well as beyond it. In particular, assorted contingent masculinities stemming from family positions of father-hood and husband-hood affect the whole research enterprise, not only in the space of ‘the field’ but also in the spaces that lie ‘before’, ‘after’ and ‘beyond’ it. Consequently, the reflective researcher is doubly troubled, by finding gender in ‘the field’ as well as determining where the entanglements of gender and field start and stop. Furthermore, the masculinities at intersection of family and field are bi-directional, spilling beyond the professional domain of the researcher’s relation to the field into the personal domain of their relation to family. By focusing on the wider implications of the masculine entanglements of family and field, gender emerges as existential epistemological condition of life. The implication is that researchers have little option but to tackle the complex challenges of gender everywhere, both in and beyond ‘the field’.