Amy Beckford Bailey was born on 27 November 1895 in Walderston, Manchester Parish, Jamaica, to Anne (née Lawson) and William Frederick Bailey. Bailey was the fifth of eight children born to her parents who were both teachers. Her father was the founder of the Jamaica Union of Teachers and encouraged all of his children to become teachers, as there were few other opportunities open to black Jamaicans. After attending elementary school at Mount Olivet Primary School, Bailey studied at Shortwood Teacher's College, graduating in 1917. Soon thereafter, she was stricken with severe dysmenorrhea. While recuperating, she studied on her own to earn accounting, bookkeeping, and shorthand.
In January 1920, Bailey began teaching at the Kingston Technical High School (KTHS), when she was hired to replace her sister who was taking a three-month leave of absence. Ivy didn't return to the school, and Bailey, who began as a shorthand instructor, remained until 1958. After she retired from KTHS, Bailey taught at the College of Arts Science and Technology between 1958 and 1963.
In 1936, Bailey and her sister Ina founded the Women’s Liberal Club (WLC), with the goal of helping women improve their employment opportunities, as rarely were women promoted for their qualifications, but instead by having to curry favour from prominent men. They believed that by improving the socio-economic status of women, they would improve their cultural and national pride. In 1939 WLC organized a conference to allow women to discuss the problems they faced. Issues they highlighted were that women were barred from participation in the Legislative Council; could not be appointed as officials, such as inspectors, jurors, justices of the peace, or police officers; were barred from upper positions in civil service jobs; and that racial discrimination impacted their employment opportunity. Bailey formalized these issues into recommendations, which were submitted to the governor in 1941 and led to a law prohibiting sex discrimination. The law allowed women to hold public office and eliminated employment bans for women.

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