In this essay, leaders of the Agency by Design Pittsburgh network Peter Wardrip, Jeffrey Evancho, and Annie McNamarra describe their process of pursuing documentation and assessment strategies for maker-centered learning that are based on the values educators bring to their work in schools and other settings. Using the metaphor of big rocks and little rocks as introduced by Steven Covey, the authors describe the process of identifying one’s values and documenting and assessing student learning from the perspective of one’s values. They then articulate the lessons they have learned and their suggestions for moving forward. The core findings that emerge from this work are: (a) identifying one’s values is challenging, (b) documentation requires practice, (c) one’s values are linked to one’s content, and (d) visibility supports measurement.