This project addresses the urgent workforce transition challenges facing Midland, Michigan. Baby Boomer retirements, a lack of structured workforce capabilities, and a Gen Z talent exodus threaten regional business continuity. Partnering with the Midland Business Alliance (MBA), our team conducted a situational analysis and comprehensive literature review, then designed four positive psychology–based professional development tools. They are tailored to the MBA’s diverse 3,000-member businesses and leverage existing strengths of credibility, diverse membership, and advocacy expertise. These positive interventions, the Legacy Transition Program, Cross-Generational Mentorship, Intergenerational Teams, and Appreciative Inquiry Summits, aim to preserve institutional knowledge, foster high-quality connections, cultivate mattering across generations, and create new innovative possibilities. In turn, the benefits to each participating MBA member organization include increased engagement, productivity, and retention. The proposed toolkits offer low-cost, scalable, and context-sensitive solutions, grounded in evidence-based frameworks such as character strengths, job crafting, mattering, high-quality connections, and psychological safety. Our approach aligns with MBA’s mission to support economic development while enhancing employee well-being, leadership continuity, and organizational resilience. Together, these strategies reframe retirement not as an endpoint but as an opportunity for thriving employee-organization, employee-employee relationships, and intergenerational collaboration.

Keywords: Positive Psychology, Succession, Retirement, Workforce Planning, Intergenerational, Professional Development, Mentorship, Mattering, High-Quality Connections, Character Strengths, Employee Engagement, Appreciative Inquiry.