Dickson graduated from George Washington High School in San Francisco, California, where he was the Player of the Year in 2008.

[2] After graduating from George Washington, Dickson attended College of San Mateo, where he was an All-American as a sophomore and helped lead his team to consecutive league titles.

He led the California Collegiate Athletic Association in runs scored and helped take his team to the NCAA Division II Baseball Championship.

[5] In 2014, he played with the AA Chattanooga Lookouts of the Southern League, where he hit .269 with 17 homers and 73 RBI[5] and scored an invite to spring training for 2015.

[9] His first major league hit was a single to centerfield off of Madison Bumgarner of the San Francisco Giants on September 23, 2017.

[13] On December 26, 2017, Dickson signed a contract with the Tohoku Rakuten Golden Eagles of Nippon Professional Baseball (NPB).