The real data on students' postsecondary outcomes are affordable, accessible, and unfortunately underutilized. If harnessed for advising high school students before graduation, these data could significantly change the approach to preparing students for college and career success across the country. How can we get more leaders and stakeholders to access and use these postsecondary outcomes data? How can and should practices change to better prepare students for college and career? How can we change the way school districts approach postsecondary advising? These questions marked the beginning of a conversation in spring 2018 that found National College Attainment Network (NCAN) staff members wondering how to accelerate the adoption of knowledge and practices from the college access field into K-12 school districts. The To & Through Advising Challenge kicked off in NCAN's conference room that day. As this report is written, the 20 grantee organizations that received funding from the Bill & Melinda Gates Foundation to participate in the Challenge are in their second academic year and implementing ambitious plans to change how they support and prepare students for their lives after high school. This brief offers up insights and lessons from five of the organizations participating in the Challenge: Jefferson County (Alabama) Schools, the Partnership for Los Angeles Schools, Broward County Public Schools (Florida), AchieveMpls (Minnesota), and Sacramento City (California) Unified School District. Rather than try to capture the entirety of their experience or practice here, each profile centers around one big idea, including steps for replicating elsewhere if feasible, and provides additional context from organizations' coaches, highlights other key practices in which the organizations are engaging, and offers the organization's insights into some big questions they faced.