Boss's Day History: Patricia Haroski, a secretary from Deerfield, Illinois, originated National Boss Day in 1958 in honor of her white-collar father, who helped all of his children with good advice throughout their careers. In honor of the elder Haroski's birthday - October 16 - daughter Patricia registered the day with the U.S. Chamber of Commerce. Four years later, National Boss Day was backed by Illinois Governor Otto Kerner who officially proclaimed the day in 1962. The idea quickly gained favor across the country and is now even observed in England, Australia and South Africa. Today, National Boss Day (or Bosses Day) always falls on October 16 and is traditionally celebrated with greeting cards, e-cards, flowers, gifts, and a few extra smiles in honor of the big Boss Man or Lady.