Penney's father was a Baptist preacher and farmer whose strict discipline included making his son pay for his own clothing once he reached eight years of age.

In 1902, owners Guy Johnson and Thomas Callahan, impressed by his work ethic and salesmanship, offered him a one-third partnership in a new store he would open.

Penney and partner Ralph W. Gwinn invested heavily in Florida real estate, including 120,000 acres (490 km2) in Clay County.

[3] After the crash, Penney lost virtually all his personal wealth and borrowed against his life insurance policies to help the company meet its payroll.

After hearing the hymn "God Will Take Care of You", written by Civilla D. Martin, sung at a service in the hospital's chapel, he became a born again Christian.

In 1940, during a visit to a store in Des Moines, Iowa, he trained a young Sam Walton on how to wrap packages with a minimal amount of paper and ribbon.

[18][19] A member of both the Scottish and York Rites, Penney was coroneted a 33rd Degree on October 16, 1945, and received the Gold Distinguished Service Award by the General Grand Chapter, Royal Arch Masons, in Kansas City, Missouri, in 1958.

[20] At the end of the Great Depression in 1939, Penney teamed with Thomas J. Watson, president and founder of IBM, Arthur Godfrey, the radio and TV personality; and Norman Vincent Peale, a minister, inspirational speaker, and author of The Power of Positive Thinking, to help Henry Simler, an executive with Remington Rand[21] form the first board of 40Plus, an organization that helps unemployed managers and executives.

The Penney Family Fund supports national organizations and state-based ones in Georgia, North Carolina, Arizona, and New Mexico that work to advance racial and environmental justice.

In 1960, Penney teamed up with the University of Missouri to establish the Penney-Missouri Awards to recognize excellence in Women's Page journalism, hoping to improve the sections where his stores most often advertised.