Based on the new perspective of syntactic analysis of the Shōbōgenzō 正法眼蔵, the chief work of Dōgen 道元 (1200-1253), it has been confirmed that the sentence structures in the Shōbōgenzō may be classified into seven types—affirmative, negative, imperative/prohibitive, interrogative/rhetorical complex sentences, expanding complex sentences, paraphrasing, and others, and many complex sentences have been used. In this paper, we aim to further clarify the syntactic features of the Shōbōgenzō through a comparison with and examination of contemporary Japanese texts, in this case the Zenkesetsu 禅家説 (discovered in Shinpukuji in 2006) and Nichiren’s 日蓮 (1222-1282) Kaimokushō 開目抄 (1272). As a result, it was possible to avoid immobilization through the substitution of words by complex sentences, especially complex expressions based on paraphrasing, and to further advance conceptualization. Further, this conceptualization prevents learned priests pursuing their studies from staying in a passive situation by requiring them to constantly confront themselves, thus compelling them to independently encounter harsh conditions to perform their ascetic practices.