When he was a teenager, he got a job as a "helper" at the Post Sign Company. However, he and his younger brother Joseph were drawing signs of their own. Then some of his work was noticed by Lloyd Branson, an elderly American Impressionist and Knoxville's best known artist. By the early 1920s, Delaney became the apprentice of Branson. With Branson's encouragement, the 23-year-old Delaney migrated north to Boston to study art. With perseverance, he achieved the artist's education he desired, including informal studies at the Massachusetts Normal School, the South Boston School of Art and the Copley Society. He learned what he called the "essentials" of classical technique. It was also while in Boston that Delaney had his first "intimate experience" with a young man in the Public Garden. Through letters of introduction from Knoxville, he also received what he referred to as a "crash course" in black activist politics and ideas; having associated socially during his years in Boston with some of the most sophisticated and radical African Americans of the time, such as James Weldon Johnson, writer, diplomat and rights activist; William Monroe Trotter, founder of the National Equal Rights League; and Butler Wilson, Board member of the National Association for the Advancement of Colored People. By 1929, the essentials of his artistic education complete, Beauford decided to leave Boston and head for New York.