In 1898, Penney began working for a small chain of stores in the western United States called the Golden Rule stores. In 1902, owners Guy Johnson and Thomas Callahan, impressed by his work ethic and salesmanship, offered him one-third partnership in a new store he would open. Penney invested $2,000 and moved to Kemmerer, Wyoming, to open a store there. He participated in opening two more stores, and when Callahan and Johnson dissolved their partnership in 1907 he purchased full interest in all three stores.
On December 26, 1970, Penney fell and fractured his hip. Just a few weeks later, he suffered a heart attack and never fully recovered. He died February 12, 1971. The Reverend Dr.Norman Vincent Peale delivered the eulogy at Penneys‘ funeral. Penney was buried in the Bronx section of New York City.