Whitaker was elected president of the New Orleans Educational Association, and served as principal of one of the largest public schools in that city.

[3] Of the six Whitaker siblings, only one other besides Lily survived to adulthood: a younger sister, Ida (d. 1925),[4][5] who was born in Augusta, Georgia.

[6] Whitaker's literary style was characterized as being "...full of grace, ideality and imagination, further possessing strength, wit and pathos".

[3] Her plays included The Useful and the Beautiful, The Study of the Rainbow, The Earth and the Ocean Peris, The Fate of Narcissus, The Golden Rod, Cupid and Pysche, Among the Stars, One Day in the Legislature, The Hobby Club, The Sunday Law, At the White House, and others numbering fifteen plays, all of which were produced at the New Orleans Grand Opera House with great success.

Whitaker's volume of poems entitled Donata, though written when a girl, won for the writer an enviable reputation.

[3] Whitaker, at her own expense, gave six receptions to a large circle of acquaintances, at each of which the actors of the day lectured upon some great play, playwright or dramatic epoch.

While in charge of the Department of Expression at St. Simeon's School, Whitaker, realizing the increasing demand for the harmonic development of physical, mental and moral faculties, began the instruction of a private class of fifteen pupils at Grunewald Hall.

This class expanded and greatly enlarged, and she added other courses and in January, 1894, the New Orleans College of Oratory was chartered by the Legislature and incorporated.

This normal department by proficiency gained the recognition and approval of the City Board of Education, and credit for work by public school teachers was given there.

Associated with Whitaker was her sister, Ida, who held the office of secretary and treasurer and was also on the staff of instructors.

From Oberammergau, the Whitaker sisters traveled through Switzerland and visited Milan, Florence, Venice, and Rome, where they had a private interview with the Pope, and then went up the Rhine to Cologne, thence to Paris.