In February 1913, Anne and Helen began a fifteen-month lecture tour in the Northeast in an effort to supplement their income from Helen's writing. At this time, John and Anne's marriage began to collapse and in May, John traveled alone to Europe. Although the reasons are unclear, Anne's fiery nature and the household's shaky financial situation may have been part of the problem. However, ultimately, John may have felt neglected by Anne in favor of Helen, and in 1914 he left the household for good. In the fall of that year, a young Scotswoman, Polly Thomson, joined the two women as a secretary for Helen.
Anne's notes and writings about her failed marriage alternate between anger toward John and sadness over a man she loved deeply:
...of the many friendships that have enriched my life, none is more interesting than that with John Macy.
In Teacher Helen describes Anne's suffering:
For days she would shut herself up almost stunned, trying to think of a plan that would bring John back or weeping as only women who are no longer cherished weep. Mother, who was staying with us, said that it wrung her to see how Teacher suffered. "I do not believe, Helen, that fate deals more kindly with a handsome, brilliant woman who has been drawn into marriage than it does with other women. Certainly Teacher was aglow with plans which a man of John's varied abilities could surely have been instrumental in developing, and now the life of which she dreamed is falling about her in ruins."
The happy light faded from Teacher's face, but she was too reserved to show her grief openly, and she refused to be comforted. To no one, except myself in the silence of the night, did she speak of her anguish or the terrible dreams that pursued her. Her health was not good. She had once exercised vigorously, but one of her chief difficulties, overweight, was causing her immeasurable discomfort. Her sight was worse, and she could not longer console herself by even short periods of independent reading. But she was steadfast in her resolve that the healthy development through which she had piloted me should not be shipwrecked by any deficiencies or maladjustments that might beset her.
In the early years after their separation John would write and ask for money; however, as the years progressed he appears to have faded from their lives. John Macy died in 1932 at the age of 55.