In 1898 Li moved to Shanghai and joined the "Shanghai Painting and Calligraphy Association", and the "Shanghai Scholarly Society" while he was attending the Nanyang Public School (later became Jiaotong University). In 1905 Li went to Japan to study at Tokyo School of Fine Art in Ueno Park where he specialized in Western painting and music, and met a lover by the name of Yukiko who was to become his concubine. In 1910 Li returned to China and was appointed to Tianjin's Beiyang Advanced Industry School. The next year he was appointed as a music teacher in a girls' school in Shanghai. He went to Hangzhou in 1912 and became a lecturer in the Zhejiang Secondary Normal College (now Hangzhou Normal University). He taught not only Western painting and music but also art history. By 1915 Jiang Qian hired him as a teacher at Nanjing Higher Normal School (renamed in 1949 to Nanjing University), where he taught painting and music. He also taught at Zhejiang Secondary Normal School (浙江兩級師範學堂), the predecessor of the famous Hangzhou High School.