“Walk in My Shoes” leverages city leadership support to allow a number of justice workers across disciplines to act as mentors to the youth enrolled in Goodwill® GoodGuides®’ 52-week, school-based mentorship program. “Walk in My Shoes” also provides program enhancements at the launch of the engagement, a special neighborhood walk for the group to build greater empathy, and an incentivized “graduation” celebration upon completion of the full program for the youth and their families. Funded in part by in-kind contributions from city and community partners and financial contributions from corporate partners, this model can be applied in communities with Goodwill® GoodGuides® programs across the region, state, and nation.