In analyses of sports activities, the phenomenological concept of optimal grip is often used to describe how a felt sense of equilibrium tells the athlete if they deviate from the optimal course of their action. Across different fields of activities, optimal grip has been used to favor progressive accounts of developing skills and expertise. However, as ethnographical studies have made aware, in several new fields of sports-related practices (e.g. life-style sports, and new trends centered round ideas of exploring ‘natural movement’) participants deliberately seek to break with performative conventions of sporting practices and presents new conditions for how to engage in movement activities. In this presentation, I explore how participants in such sports-related activities contribute to broaden the scope of optimal grip and, accordingly, the ways in which embodied knowledge production can take place. The project presents my fieldwork with Fighting Monkey (https://fightingmonkey.net/ ) involves a cultural phenomenological approach as defined and discussed by, between others, anthropologists like Csordas (1990, 1993) and Zigon & Throop (2021). Sports-anthropologically, Fighting Monkey can be described as part of a counterculture confronting (traditional) sports ideals of progression. . Interestingly, Fighting Monkey does so by continuously developing different kinds of explorative and playful activities, using, between others, obstructive approaches, and task-based improvisation often in combination with different kinds of materiality and tools (e.g., sand and clay). By both challenging and exposing participants’ embodied world involvement, their embodied knowledge of optimal grip and skilled participation are put at risk as well as confirmed but on new and, at times surprising conditions. Optimal grip is thereby displayed as perceptually attuned resources that underlies participants’ ability to negotiate new and unpredictable situations and at the same time, the Fighting Monkey activities, pushing for explorations and potential failure, facilitate embodied experiences of the world also “gripping” the practitioner moving.