This paper highlights the authors' experiences teaching high school students Science-Technology-Engineering-Mathematics (STEM) and technology literacy skills. Productive learning is engendered by trust, safety, supportive interpersonal relationships between mentors and students, and adaptation of teaching style to match the students' frame of reference. These principles are incorporated in the design of an online learning program called Best We Can Be. We discuss how technology-aided instruction encourages students to explore subject matter beyond their comfort zone. This fosters students' natural curiosity about STEM topics, and helps overcome their anxiety about whether they will be able to learn the subject matter. In Best We Can Be, students participate in structured, hands-on activities illustrating the cross-fertilization of academic disciplines (e.g., bioethics, which encompasses social, health and biological sciences, humanities, law, etc.) and their interdependency in society. We examine technology's enablement of student interactions within secure networks of mentors, experts, and peers. We discuss transformative impacts of broadening student appreciation of the world of possibilities that await them in future educational and career paths. The ultimate goal is for students to become self-motivated, life-long productive learners.