The young men had known each other all of their lives, having grown up only a block apart in Hamilton, Missouri. Although James C. Penney was six years older than James M. McDonald and had gone to school with the older McDonald boys, J.M. had been a frequent visitor in the Penney home, drawn by Pearl, a sister who was his age. Their mothers were close friends and visited each other regularly. Their fathers were both members of the Hamilton school board as well as political contemporaries.

After about six months in Kemmerer, J.M. went to Spokane, Washington. His brothers had gone there and asked him to join them in a department store venture. In the ensuing years, he added to his experience of merchandising and buying and made a success of whatever he undertook.

On September 1, 1911, J.M. went back with J.C. Penney as an assistant manager in their 25th store in Pendleton, Oregon. Prior to this, while in Spokane, J.M. met a young nurse, Josephine Armstrong, a graduate of Minneapolis City Hospital, who was doing private duty nursing in the various Spokane hospitals. They were married on December 10, 1910. When J.M. went to Pendleton in 1911, the couple was expecting their first child the following February, so Mrs. McDonald stayed with J.M.'s parents, who had moved to Spokane to be near their sons.