The primary purpose of this paper is to clarify the relationship between Montessori educational thought and the influence of theosophy in Montessori’s work before, during (1939–1946), and after the period she stayed in India. The image of the Montessori method is corrected by consideration and various concepts of the Montessori method compared with theosophy are presented as a new perspective. A peculiar vertical paradigm related to theosophy as a “relationship that I conform to the universe” and a “transformation of the subject for the rise of the spirit” is shown as an effective index for understanding Montessori educational thought. Through a profound perspective based on concepts such as holism, various concepts of the Montessori method, such as “social reformation,” “order,” “concentration,” “work,” and the “sensitive periods” are reviewed as a “prelude to religious awakening.” This vertical paradigm can also be found in Steiner educational thought. The second purpose of this paper is to introduce the practice of both therapeutic education systems based on this vertical paradigm.