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This paper explores whether human proactivity can be considered an expression of free will. The discussion involves two paradigms, which are mutually complementary and encompass psychological proactivity and reactivity. Both paradigms raise the question of linear and non-linear determinism, which inevitably leads to the issue of free will. The analysis attempts to find a compromise between linear and non-linear determinism through the approach of human dialectical complexity (Lebed & Bar-Eli, 2013). This refers to the relationships of two types of complex subsystems within a human: the perceptual-motor dynamic system (PMDS), which is mostly determined by linear impacts and expressed through reactive behavior, and the “free-will” 1 complex system (FCS), which is mostly determined by non-linear redundant determinism and expressed through proactive dynamics. In summary, it is concluded that there cannot be a categorical assertion of the permanent existence of free will in human functioning. The human dialectical complexity expressed by both proactivity and reactivity causes the “floating” presence of free will depending on the prevalence of proactive control factors and the non-linear determination of a living human system. [ABSTRACT FROM AUTHOR]