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The unique organization and structure of On Freedom is intended to render the content more accessible to readers. Each chapter (including the Introduction and Conclusion) is made up entirely of short vignettes, most ranging from two to three pages, that are somewhat self-contained. They include anecdotes from Snyder’s life, historical information, references to philosophers, and current events (usually American). While there are some callbacks to other anecdotes, for the most part when Snyder relays a personal story within a vignette, it is uniquely relevant to the topic. This shares some similarity with Snyder’s similarly titled On Tyranny, his most popular work, which contains 20 short lessons from 20th-century authoritarianism that can be applied to the modern day. 

Whereas On Tyranny was simplified for readers with only a cursory understanding of American government, On Freedom requires slightly more focus and attention. Vignettes are grouped into thematically-titled chapters, a less defined structure than that of On Tyranny, owing to On Freedom's philosophical exploration of freedom and new ways of defining it. The vignettes often utilize terms of Snyder’s own design (e.g., negative freedom/positive freedom, politics of eternity) and sometimes dense political science vernacular (e.g., imperial mobility). The short, contained nature of the vignettes allows Snyder to break up the material into smaller pieces and urge readers to reimagine their understanding of freedom in an approachable way.

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