Dai started to write for the Shanghaiese China Foreign Daily (中外日報) and Tianduo Newspaper (天鐸報) at 19.

The Qing officials threatened him with imprisonment for his writings, so in 1911 he fled to Japan, and then to Penang, where he joined Tongmenghui and wrote for its Guanghua Newspaper (光華報).

Dai's fluency in Japanese, unusual for a Chinese young man, attracted the attention of Sun Yat-sen.

In 1926, he served as principal of the Sun Yat-sen University, and the chief of politics at Whampoa Academy, with Zhou Enlai as his deputy.

From October 1928 to June 1948, his official positions consisted of: Dai was one of the lyricists of "National Anthem of the Republic of China".

According to popular speculation, Dai believed knowledge of his extramarital affairs with the Japanese woman Shigematsu Kaneko would destroy his marriage and his career, so he entrusted Wei-kuo to Chiang Kai-shek, after the Japanese Yamada Juntaro (山田純太郎) brought the infant to Shanghai.