A constraints-based framework enables a new understanding of expertise in outdoor adventure sports by considering performer-environment couplings through emergent and self-organizing behaviours in relation to interacting constraints. Expert adventure athletes, conceptualized as complex, dynamical movement systems, pick up affordances for action to regulate adaptive transitions between functional movement behaviours. For example, icefall properties contain affordances that can induce variable motor coordination patterns in expertclimbers, whereas beginners use a basic and stable motor organization to achieve the main goal of maintaining body equilibrium with respect to gravity. Movement pattern variability could play a functional role as individuals adapt their behaviours to ecological constraints of performance by exhibiting multistability and metastability. The properties are exploitable by coaches and educators who can use system instability to stimulate creativity and skill acquisition. In this way, expertise relates to the neurobiological property of adaptability, a subtle blend between stability and flexibility, as experts are able to be stable when needed and variable when needed. We highlighted a new emphasis on how novices and experts individually manage motor system degrees of freedom in coordinative structures through redundancy or degeneracy as they structurally adapt system and sub-system organization to achieve functional goals. The main implications for adventure athletes are to identify and manipulate key constraints to perturb and create emergence of appropriate behaviours rather than to encourage the imitation of a single response in reference to a putative ideal expert model. Indeed, imitating so-called ‘expert behaviours’ could lead to frustration and a prolonged skill-acquisition process, as novices may encounter difficulties in matching the required behaviours. Using a constraint-led approach could lead to the emergence of individualized movement responses directly related to the preexisting intrinsic dynamics of a performer in outdoor adventure sports.