In this article, I share two lessons learned through engagement in practitioner inquiry. The purpose of my inquiry was to understand self-regulated learning as it developed in students receiving intensive instructional supports within a newly designed 21st century learning space. I illustrate each lesson with salient excerpts from three types of data: field notes, student artifacts, and my own daily journal entries. Prior to my discussion of these lessons learned, I define self-regulated learning and describe how I applied it to my Tier-3 instructional practice. This study affirms the importance of structure when first introducing self-regulation to students, and additionally provides insights into what it takes to put effective structure into place.