Early in his career, Douglas briefly taught at Lincoln High School in Kansas City, Missouri before coming to the attention of Harlem Renaissance luminaries. Impressed with Douglas’s talent and ambition, Charles Johnson enticed Douglas to add his talent and voice to the discourse that was happening in Harlem.

Douglas’s arrival in Harlem coincided with the release of the landmark publication “Harlem: Mecca for the New Negro,” in the the March 1925 issue of Survey Graphic which included an introductory essay by Alain Locke, founder of the New Negro movement. By Douglas own admission, “it was the single most important factor in his decision to move to New York.” Douglas’s relocation to New York was fully “immersive.”

He was quickly enveloped into the cultural and intellectual community in New York. Douglas to studied with German émigré artist Fritz Winold Reiss, a well-renowned graphic designer and artists whose vibrantly colored images and interior designs graced the covers of publications such as Opportunity Magazine and the Apollo Theater. One of the greatest influences on Douglas’s work, however, was his decision to study African art. His adaptation of African inspired design elements, aligned with that of Europeans modernists and is reflected in Douglas’s work that appeared in Opportunity and The Crisis. The artist enjoyed unparalled level of popularity which provided him with led to an invitation from W.E.B. Dubuois to join the staff of The Crisis. He was recruited by James Weldon Johnson to illustrate Johnson’s "God’s Trombones: Seven Negro Sermons in Verse." Douglas left Harlem to study briefly to study abroad in Paris. However, his patronage was undiminished during the time he was in Europe where he studied at the Académie Scandinave.

Douglas’s legacy includes founding Fisk University’s art department; helping to establish the Harlem Artists Guild, along with famed sculptor Augusta Savage, muralists Charles Alston and Elba Lightfoot, and writer Arthur Schomburg. The guild most notable efforts included persuading the Works Progress Administration to generate more opportunities for African-American artists. He is credited with establishing the Carl Van Vechten Gallery at Fisk and helping to secure some of the collections most seminal works.