Init2Winit is a gamified mobile application designed to promote college and career knowledge among adolescents. Init2Winit offers students multiple opportunities to explore college and career pathways using game tunnels; this tunnel play informs students' understanding of how mis/aligned choices can have varying consequences for their future. Our study examines player performance in the career tunnel--where students attempt to align their educational expectations with chosen career pathways. Students earn points when their educational expectations are correctly aligned with their desired careers and expected salaries. Init2Winit was tested in Midwest urban and rural high schools using a sample of 186 high students. Results show that students who earned high alignment scores increased their college-going expectations. Subsequent game plays increased students' alignment between college choices, career plans, and realistic salary projections.