Masefield lived as a vagrant for several months, before returning to New York City, where he was able to find work as an assistant to a bar keeper. His wages were $10.00 per month plus room and board, and his hours of work were from 9:00AM to 2:00AM. Although this was grueling, his desire for writing did not ease, and Masefield continued to make time for reading whatever he could find, and writing poetry. Although his employment only lasted 2 months, Masefield did enjoy a close friendship with his bar keeping boss and family, and later in his life on a return journey to America, Masefield made a point of returning to visit with him.

For the next 2 years, Masefield was employed in a carpet factory. During this time, long hours were expected of all employees and conditions were far from ideal, certainly not for a young man intent on becoming a writer of stories and poetry. Masefield�s determination was great enough, however, for his dreams to survive, and he continued to spend much of his time reading and writing. He would purchase up to 20 books per week, and devoured both modern and classical literature. His interests at this time were diverse and his reading included works by Trilby, Dumas, Thomas Browne, Hazlitt, Dickens, Kipling, and R.L. Stevenson. Chaucer was also to become very important to Masefield during this time, as well as poetry by Keats and Shelley. Towards the end of this period of his life, the spark of desire to write and become a poet was kindled into a fire, and he yearned to return to England with the hope of being able to achieve his goals.