She continued auctioneering for nearly 20 years and wrote a book about her experiences, entitled Sold to the Lady in the Green Hat (1962), before retiring in the late 1960s.

[1] Since their new home was an old house in need of repair, and the family was having difficulty paying bills, Bailey decided to start an auction business to supplement her husband's income.

[3] Her Saturday auctions soon became a regular local event, and her family helped out: Bailey's husband organized the sale items, and her daughters did the record-keeping and sold concessions.

[2] Bailey sold a wide range of items, including antiques, farm tools, books and household furniture,[3] and was known for her "poetic" promotional descriptions of wares.

She developed a reputation for fairness and "scrupulous honesty," once putting police onto a group of antiques thieves who had approached Bailey under false pretenses for help selling their goods.