Over the next decade, he intermittently pursued a public education while working various jobs as an oyster culler, hack driver, and steamboat waiter.

[1] Following several jobs as a waiter at resorts and servant for prominent families, Fields became employed as a butler for Alonzo B. Cornell, who served as Governor of New York from 1880 to 1882.

In 1887, Fields enrolled in the inaugural class of Cornell Law School, graduating in 1890 and having authored a thesis titled Trial by Jury.

Although he lost his sight in 1896, he became a leading lawyer in the area with a large law practice of both white and Black clients, and he was active in several community organizations.

Their son died in infancy, but their daughter, Inez C. Fields, became the second Black woman admitted to the Massachusetts Bar and worked for William H. Lewis.