How do we partner with families to help transition their children into High School with an eye toward the many paths to future success? What aspirations do they have for their children and do they know if their child is on track to achieve those aspirations? How can parents foster critical life skills to help navigate change, added responsibility and more? How can we help parents lean into their child’s interests and strengths to foster student agency? What are some of the milestones to consider for various college and career pathways? These and other questions were explored in the second in a series of webinars from Learning Heroes and Remake Learning Days Across America.