James Frederick Failing was born in New York on March 24, 1842 to Josiah Failing and Henrietta Legge Ellison. His father and older brothers, Henry and John William, arrived in Portland in 1851, followed two years later in 1853 by James, their mother, and sister, Elizabeth. James completed his education at Portland Academy, then joined J. Failing and Co. as a clerk. The company was a wholesale hardware business started by Josiah and Henry Failing at the corner of first and Oak Streets. James later became a partner at Corbett, Failing and Company. The company operated under this name for 22 years, before later becoming Failing-McCalman Company, operated in part by James's three sons.

In 1877, James Failing became a director of the First National Bank in Portland, remaining a senior director until his death in 1920. He married Jane Johnson Conner in 1880. She was born in Albany, Oregon on February 14, 1855 to merchant John Conner (1820-1902) and his first wife, Martha Mariea Bancroft Whittlesey (1827-1861). Later, John Conner married James's sister, Elizabeth Ann Failing in 1863. Jane Conner and James F. Failing had five children: Edward Josiah (1881-1936), Kate Whittlesey (1883-1971), John Conner (1886-1951), Frederick Ellison (1892-1929), and Henrietta Chase, 1895-1989). Kate and Henrietta participated regularly in Portland civic life, volunteering with numerous organizations.

James Failing and his family were members of the First Baptist Church of Portland. He was involved in the development and construction of the church's Taylor Street building between 1892 and 1893, and was both a trustee and a deacon. His daughter Kate created scrapbooks documenting the history of the church. He was also a director of the Young Men's Christian Association and a trustee for McMinnville College (later known as Linfield College), and an active member of the Oregon Pioneer Society and the Auld Lang Syne Society. Both his father, Josiah, and brother Henry served as mayors of Portland. While James never held public office, he was regarded as a prominent individual in the Portland business and civic communities.