Outland was born in Hesper, Kansas to Thomas Outland and Mahala Outland (née Kemp) into a Quaker family who settled in Kansas from Indiana around 1860 during the Bleeding Kansas period as part of a larger Quaker immigration to Kansas in support of the Free state cause. He grew up mostly in Johnson County, Kansas in the towns of Lexington, Kansas and Edgerton, Kansas though. He was a member of the first football team at Penn College in Oskaloosa, Iowa in 1891. Outland captained the team in 1892, scoring 32 of the team's 36 points. After starring in football and baseball at the University of Kansas in 1895 and 1896, Outland went to Philadelphia to complete his medical education at the University of Pennsylvania. There he became one of the few men ever to win All-American football honors as b