Upon graduation he attended East Central University in Ada, Oklahoma, and was a three-year letter winner as quarterback of their football team.

He used that experience to gain a head coaching position in 1983, at one of the premier football programs in Oklahoma, Davis High School.

After concluding one full season, Dickinson became a graduate assistant for the University of Oklahoma (1983–85), where he was part of the 1985 Sooner National Championship team coached by Barry Switzer.

At the conclusion of the season, Dickinson took his play-calling skills to Northern Illinois University where he served as offensive coordinator and quarterbacks coach from 1991 to 1995.

Here, he was attributed with bringing in highly touted recruiting classes and helped the Central Oklahoma Bronco quarterbacks pass for 8,944 yards and over 40 touchdowns in his four seasons with the team.

Throughout his coaching career, he has been credited to work with NFL quarterbacks Bubby Brister,Troy Aikman, J. P. Losman, Patrick Ramsey, Gus Frerotte,[9] Rudy Carpenter, Josh Freeman,[10] Rhett Bomar,[11] Matt Barkley,[12] Chase Daniel, Tyrod Taylor, Josh Johnson, and Mac Jones.