Religion shouldn’t reinforce all of your ideas about the world. It should challenge you and push you to recognize uncomfortable truths about yourself and the world and spur you to transform both. So says Rabbi Shai Held, the co-founder of the Hadar Institute and a man who’s been named to the Newsweek/Daily Beast list of “Top 50 Most influential American Rabbis” numerous times.

He was in town recently to talk about his new book, The Heart of Torah: Essays on the Weekly Torah Portion. With the upcoming Jewish High Holy Days in mind, Held talked about a range of ideas, including how he grapples with the awesome power of religion, and how it’s used.