This paper describes ongoing research exploring how a place-based collaborative approach to design has the potential to enhance learning experiences for young people and businesses, as well as raise awareness of future employment opportunities in the local area. It highlights current challenges in skills and education, focusing on how a new approach to tackling these issues could be nurtured through design. The paper explores two projects in towns in the North West of England that have barriers to future work opportunities, in which collaborative design processes are having a positive influence on young people, businesses and the wider community. In the first project, a design company, youth workers and design researchers are designing a digital intervention for young people and businesses to connect through learning and work experiences. In the second project, a creative practice, secondary school pupils and design researchers are co-designing a place-appropriate programme of activities to be included in a major festival in the North West. This paper concludes with findings on how a co-design approach can engage and inspire local young people and businesses around future work opportunities, shape learning experiences, as well as foster resilient, sustainable communities, an area to be explored further in design research.