An inspiring teacher, Dickey was on the faculties of Cornell University and Denison University before taking a position at San Francisco State University, where he taught English and creative writing for almost 30 years until his retirement in 1991. He received an award for classroom excellence from the California Association of Teachers of English.
Modern technologies captured Dickeyıs interest: he taught a graduate seminar on multimedia computer poetry and wrote poetry in that medium. His essay "Poem Descending the Staircase: Hypertext and the Simultaneity of Existence" was printed in the 1991 book Hypermedia and Literary Studies(MIT Press).
Dickey wrote about his Reed memories for his 40th reunion, in 1991: "Of influences that changed me at Reed, Lloyd Reynolds, both as a teacher of creative writing and as a calligrapher and typographer, was surely the most radical, though I owe a debt of gratitude to other faculty members as well, particularly including Donald MacRae."
Dickey graduated Phi Beta Kappa from Reedhis creative writing thesis was a 290-page novel called Chaldeaand earned further degrees in creative writing from Harvard University (M.A. 1955), supported by a Woodrow Wilson fellowship, and the University of Iowa Writers' Workshop (M.F.A. 1956). He was later a Fulbright Fellow at Jesus College, Oxford University.