Robert began his involvement with periodical publishing as a feature writer and weekly columnist for The Northern Review, Ohio Northern University’s print newspaper. He later became the editor-in-chief of the same publication, as well as a stringer for the local "Ada Herald". During this time, his academic writing and field research focused on understanding and depicting the lives of musical street performers.

While in graduate school at Stetson University, Robert served as a funded composition consultant in the writing center as well as a teaching assistant for the English department’s ecological writing course. In a related venture, he created a blog, focused on conveying the natural side of Florida through his own photography and writing. During this time, Robert also released original music with the multimedia insert in Touchstone, Stetson’s literary journal, and he composed his master's thesis, addressing structural contributions to the creation of American identity through Ernie Pyle’s dispatches from North Africa.

After completing graduate school, Robert briefly covered all beats as a staff reporter and photographer for The Gadsden County Times. He then began his career in education by returning to Stetson as an adjunct instructor before eventually progressing to a full-time position at Eastern Florida State College.