For many historians, the path towards writing a first book seems relatively clear. Most first books, after all, begin as dissertations that have been conceptualized, researched, and written in conversation with a committee of advisors and graduate school colleagues. This roundtable seeks to address the question of strategizing and conceptualizing a second book project. It brings together a number of different perspectives – from tenure-line faculty and unaffiliated scholar to editor – to discuss the challenges and opportunities of the second book.