However, his position was not stable as shown by the fact that he was appointed as Daisōjō four times back and forth following his brother Kanezane's ups and downs in the political world.

[2] This is because as the leader of Tendai, in addition to holding rituals and maintaining Buddhist monasteries, he also served politically as the guardian of Kujō Michiie, the grandson of his brother Kanezane.

Jien eventually began to study and write Japanese history, his purpose being to "enlighten people who find it hard to understand the vicissitudes of life".

When Emperor Go-Toba attempt to overthrow the Shogunate, Jien, fearing that the Kujō family would be affected, began to trace the history of Japan and wrote Gukanshō, a combination of History, Buddhist ideas and legends, to try to dissuade emperor Go-Toba from overthrow the Shogunate.

[4] Overall, he wanted to help people, especially the Emperor, to come to understand Dori through Japanese history so that he could shape a desirable future and help the country go through mappo.

In The Unfettered Mind the Zen Buddhist Takuan Sōhō cites the following poem from Jien, interpreting it in the context of No-Mind:[5] The flower that would surrender its fragrance before my brushwood door Does so regardless.