In the early years of the 20th century a small community or colony on Monte Verità near Ascona at the Lago Maggiore became refuge and encounter for different representatives of the Lebensreform. Main issues culminated here, and here the representatives conflicted with each other. Controversial response proposals uncovered the fundamental divergencies of a naturalistic world view. Thus, Monte Verità spotlights pedagogical problems in the context of Lebensreform and Reformpädagogik. Based on the writings of the respective protagonists and their environment, and referring to repeated visits to the Monte Verità, we propose a reflection of its development and central motives and deconstruct critically the understanding of the child and the new conception of the educator on the ‘Mount of Truth’. Ida Hofmann, as one of the main founders, individualist, and naturalist Gusto Gräser and the psychoanalyst and anarchist Otto Gross shaped essentially Monte Verità and formulated the motives that still nowadays keep floating like a will-o’-the-wisp in the models of Reformpädagogik. Education is always tempted to ‘tame’ contingent structures, to anticipate an uncertain future and to define clearly the role of the educator. Frequently teleological suppositions sneak into the educational praxis and confer the present action an image of validity and offer the educator tranquilizing certainties. Monte Verità represents a clear example for this. To understand pedagogical thinking as focusing on growth with open results, therefore guided by an anthropological perspective, requires a clear decision for continued questioning of subtle basic presuppositions. Instead of mental certainties, the search for always new, concrete, child-centered educational action, in short, an education that parts “from the Child”.