Ann's paternal figure held a prestigious position within the Ministry of Defence, which led to a nomadic upbringing for her, as she attended various educational institutions around the world. Her formative years were spent at the Royal Naval School in Singapore, followed by La Sainte Union Convent in Bath, before she matriculated to Birmingham University to pursue a Bachelor of Arts in Latin, graduating in 1969.
Upon completing her undergraduate degree, Ann proceeded to Lady Margaret Hall, Oxford, where she earned a Bachelor of Arts in Philosophy, Politics, and Economics in 1972, and later a Master's degree. Her professional journey commenced with Unilever in the marketing department from 1973 to 1975.
Subsequently, Ann relocated to London University in 1975, where she held the position of senior administrator. However, she departed the academic sphere to pursue a career in politics in 1987. Throughout her tenure, Ann gained notoriety for her candid remarks, including a memorable instance in 1997 when she accused her political superior, Michael Howard, of having "something of the night" about him, following a departmental dispute. This seemingly hindered his professional advancement until he was unexpectedly elected leader of the Conservative Party and the Leader of Her Majesty's Loyal Opposition in November 2003.
In 2001, Ann resigned from the shadow cabinet and declined to participate in the leadership election, marking a significant turning point in her political trajectory.
