This document provides a retrospective on major developments in open educational resources (OER) over the past 20 years. It discusses key choice points that helped shape the field, including: adopting open source to redistribute power; using open licensing to facilitate collaboration; pursuing sustainability to support long-term creation and use of OER; prioritizing interoperability to improve discovery; promoting open textbooks for awareness; and increasing supply to drive adoption. The document also outlines the CARE framework for OER stewardship and notes some current choice points like navigating intersections with other disciplines and defining commitments to accessibility and inclusion.