The winner of the 2018 Pozen Prize for Innovative Schools— the Edward M. Kennedy Academy for Health Careers (EMK) in Boston— seeks to empower underrepresented students to succeed in college and high-wage careers. With an emphasis on healthcare-related career exposure and experiential learning, the school places a deliberate focus on preparing every student with the skills they need to succeed in fields related to science, technology, engineering, and mathematics (STEM). Taking part in a rigorous college preparatory program, students know that simply getting to college is not the goal. Instead, their school equips them with the habits of mind that will prepare them to graduate college with the skills needed for a STEM related career. This case study highlights the key practices that have facilitated the EMK’s success, including an exploration of the school’s healthcare theme as a vehicle for practical college and career planning and the impact of community partnerships and supportive student and staff relationships.