Masaoka attended the Japanese department of Tokyo Imperial University with Natsume Sōseki and Akiyama Saneyuki, later dropping out to work as a columnist for the newspaper company "Nippon".
Masaoka attended the Japanese language department of Tokyo Imperial University with Natsume Sōseki and Akiyama Saneyuki. However, he became fascinated with literature and eventually forfeited a scholarship by dropping out in 1892 to work as a columnist for the newspaper company "Nippon".