This session offered a fresh perspective on how to support learning in foundations or nonprofits. We broke from conventional thinking that better learning is simply a technical problem solved with the right tool, the right template, or even the right data and findings. We applied a systems lens to the challenge of learning, looking at it from unexpected angles and across multiple disciplines, identifying how the day-to-day ways in which we think and work impact our ability to learn. We explored questions such as: How do our biases get in the way? Do open space workspaces support learning? How do organizations actually reward and incentivize learning? Participants walked away with ideas on how to cultivate learning as an everyday practice—a way of working and thinking and a set of habits.