In 1919, he visited Japan for the first time on a school trip that lasted 18 days—it was an eye opener.
In 1927, he joined the Kurisha Poetry Society [zh], a group that would produce some of Taiwan's best known modern poets.
Ten years later, he managed to secure an appointment as "Chief Disciplinarian [zh]" of the schools in Kansai, Shinchiku, but he resigned in 1940, following an incident in which the teachers were insulted by the Japanese authorities.
[1] He stayed in China for 15 months and returned home in 1943 and took a position with the Taiwan Daily News.
At that time though, emphasizing Taiwanese identity was still politically controversial and Wu was pressured by the authorities to drop 'Taiwan' from the title of his magazine.