Drawing from the most recent scholarly studies in the books of Proverbs and Ecclesiastes, this commentary promotes deep theological reflection. In addition to the imaginative artwork used for illustration, readers will find a broad appeal to contemporary literature and authors as touchstones for applied reflection. These books both use universal concepts and images and lack a particularistic appeal to ancient Israel’s nationalistic story. These examples of wisdom literature in the Hebrew Bible may be some of the most relevant Biblical writing for our contemporary setting. For this reason readers are invited to recontextualize the wise council of Israel’s ancient sages through the perspectives of contemporary literature.