This chapter will provide an overview of career theory and practice for working with youth who choose an alternative postsecondary plan in lieu of pursuing a four-year college degree. Utilizing Young’s ecosystems theory, in conjunction with brief solution-focused techniques, school counselors and career advisors can successfully guide students toward success after high school. The authors will explore options that may appeal to Gen Z students through paths to education, job training, and careers in the emerging fields of eSports and iGaming.