At age 15 Shiki became something of a political radical, attaching himself to the then-waning Freedom and People's Rights Movement and getting himself banned from public speaking by the principal of Matsuyama Middle School, which he was attending. Around this time he developed an interest in moving to Tokyo and did so in 1883.
The young Shiki first attended his hometown Matsuyama Middle School, where Kusama Tokiyoshi, a leader of the discredited Freedom and People's Rights Movement, had recently served as principal. In 1883, a maternal uncle arranged for him to come to Tokyo. Shiki was first enrolled in Kyōritsu Middle School and later matriculated into University Preparatory School. (Daigaku Yobimon) affiliated with Imperial University (Teikoku Daigaku). While studying here, the teenage Shiki enjoyed playing baseball and befriended fellow student Natsume Sōseki, who would go on to become a famous novelist.