The Design Day brought together youth sector stakeholders – youth, youth workers, policy makers, researchers, funders and citizens – to collaboratively tackle four ‘thorny’ challenges, or Idea Labs, that youth and youth workers experience. This event was hosted in collaboration with the Youth Opportunities Fund at the Ontario Trillium Foundation. This report is a snapshot of this Design Day and includes the four Idea Lab challenges that the Design Day focused on and the eight prototype pitches that participants co-developed in response to these challenges. The report includes reflections on the collaborative process along with resources and case study examples that can inspire our youth work.