The paper analyzes the emergence of the concept of motive in Alexey N. Leontiev’s early writings and its correspondence to Kurt Lewin’s ideas and to the distinction of intrinsic versus extrinsic motivation and the concept of the continuum of regulation in the present day self-determination theory of E. Deci and R. Ryan. The distinctions of extrinsic motivation based on reward and punishment versus “natural teleology” in K. Lewin’s works and of (extrinsic) motive versus interest in early A. N. Leontiev’s texts are explicated. The relationships between motive, goal, and personal meaning in the structure of activity regulation are analyzed. The author introduces the concept of quality of motivation referring to the degree of correspondence between motivation and one’s needs and authentic Self at large; the complementarity of activity theory approach and self-determination theory as regards the quality of motivation issue is highlighted.