He went on to earn his doctorate at the University of Leipzig in Germany in 1901 under the direction of Eduard Sievers and Albert Köster.

Fife was a German teacher at St. Alban's School in Radford, VA (1895-1898) before continuing studies at Göttingen and Leipzig from 1898 to 1901.

Fife's first position at an institution of higher education was as an instructor of German at Western Reserve University (1901-1903).

At Wesleyan University, he remained a Marcus L. Taft Professor of German Language and Literature until 1920.

[3][4] After staying at Wesleyan University, Fife replaced Calvin Thomas as a professor of German at Columbia University in 1920[5] and upon his appointment at Columbia, received the Gebhard Professorship.

[10] Fife also served as the chairman of the Committee on Modern Language Teaching of the American Council on Education.