The question arises whether or not Anne would have chosen a different path for herself if she could have, rather than remain with Helen her entire life. John D. Wright, in the 1890s, noted her musical talent and Helen recorded that her teacher had a love and aptitude for sculpture. Anne was an excellent equestrian and loved poetry. Her letters and essays reveal a very talented writer. However, her thoughts reflect a degree of fatalism as to life's eventual outcome. In Nella Braddy Henney's book Anne Sullivan Macy, Anne is quoted as follows:
I have never known...the deep joy of surrender to my own, I cannot say genius, since I have not that immortal gift of the gods - but to my own individual bent or powers. I have been compelled to pour myself into the spirit of another and to find satisfaction in the music of an instrument not my own and to contribute always to the mastery of that instrument by another.
How often I have been asked: "If you had your life to live over, would you follow the same path?" Would I be a teacher? If I had my life to live over I probably should have as little choice of a career as I had this time. We do not, I think, choose our destiny. It chooses us.
In 1932, four years before she died, she again considered teaching. This time her pupil was to be a baby who was deaf-blind, however she was disuaded from doing so. The little documentation that we have suggests that her own volatile nature (and perhaps her bouts of ill-health) impaired her ability to focus her own talents. Moreover, her poor working-class background was perhaps a constant reminder that to remain Helen's teacher was a far more reliable way of ensuring a secure future. In Foolish Remarks of a Foolish Woman, she wrote the following:
I hate a mapped-out life, yet I can't find a centre within myself to grow from. Growth requires time and patience, yet I can't let them be. I am impelled to dig up the acorn and see if the oak has sprouted. Only in Helen have I kept the fire of a purpose alive. Every other dream flame has been blown out by some interfering fool.