2 Degree Shift Work-Based Learning (WBL) reverse engineers the needs of employers or organizations’ desired skill sets, capacities, and capabilities. In working with youth, the goal is to increase student engagement with industry and their communities. WBL research and data highlight job shadowing, internships, and apprenticeships as valuable learning avenues; however, these work experiences are often logistically difficult. Challenges arise in transporting hundreds of youth to job sites or asking a busy parent to line up an office opportunity for teens. Thinking about ways to simulate WBL, addressing where learning occurs in organizations, and examining needs and expectations is critical. We focus on preparing and supporting learning to build the learner’s confidence to engage and prepare for deep learning in collaboration with others. We seek to co-create and develop the capacity that leads to success for youth in speaking up and sharing ideas, interviewing for a job, and gaining skills to earn a place at the table. Practice and participation solidify learning and accelerate careers. Our approach assumes the logistical challenge and the desire for meaningful learning toward earning and thriving in livable wage jobs.