This study is an interpretation of the democratic thought of the Progresive-era United States, focusing on the role of work in the writings of Jane Addams, Herbert Croly, and John Dewey. Many other thinkers of the period turned their attention to questions of work, but Addams, Croly, and Dewey played public roles that made them uniquely influential. This study is a close reading of the work of these three Progressive thinkers. It focuses exclusively on their writings that bridge the nineteenth and twentieth centuries, identifying the period between the Pullman Strike of 1894 and World War I as a critical juncture in the development of their thought. Relying on a close reading of their academic writings, periodical pieces, public addresses and social commentary, the analysis critically examines themes of labor, occupation, and vocation, using the writers' own words to illustrate and interpret not only what they thought about work, but also how central it was to how they thought about democracy.