This practical resource describes key approaches to help educators, counselors, and administrators to revise their own practices to better support the college aspirations of today's diverse students. This book encourages educational practitioners to reimagine school-based, postsecondary preparatory opportunities to be more inclusive, cohesive, and supportive of students and their families. With specific attention paid to students who have been traditionally underrepresented in college-going and college-graduating populations, the authors use theory, research, and empirical evidence to intentionally center and elevate students who have been overlooked or marginalized in the postsecondary planning process. Based on a college and career readiness program that supported the postsecondary aspirations of Black teenage girls, this book identifies how, where, and when school policies and practices create barriers to college and career planning. Within that program, traditional postsecondary practices were redesigned with specific consideration of the essential elements of time, care, cultural relevance, and lived experiences. Book Features: (1) Challenges school practitioners, administrators, and district leaders to reexamine the policies and practices they are using to prepare students for postsecondary lives; (2) Demonstrates how to intentionally dismantle one-size-fits-all approaches to postsecondary preparation by centering the needs of diverse students; (3) Includes insights and reflections from a three-year college and career readiness program in a public high school in partnership with a group of Black teenage girls; and (4) Provides intentional strategies for including race, class, and gender in postsecondary planning.